Inspirational profiles of women in
leadership roles in the tech scene.

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Lead(H)er Profile - Ashima Dua, Director of B2B Product at Outcomes4Me banner image

Lead(H)er Profile - Ashima Dua, Director of B2B Product at Outcomes4Me

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Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Ashima Dua, Director of B2B Product at Outcomes4Me.


Where did you grow up and how would you describe yourself as a child?

I was born in India and came to the U.S. with my parents when I was 5 and my brother was 4.  We were lucky to have my uncle and aunt (from both sides) to help us adjust to a new country.  I loved my childhood growing up in Somerville, Mass. During the year, our days were spent going to school and playing with the other kids on our street. It felt like a big, community family with members from many places around the world. Summers meant either spending more time outside with trips to area locations or visiting family in India. I always felt lucky that I had the opportunity to be immersed in two cultures and enjoy the richness that comes with that. 

What did you study in college and what was your first job out of school?

I studied computer science at MIT and actually thought I was going to be an engineer when I graduated. Working as an engineer was my first job out of school, but I never coded. When I was hired, my company transitioned to a globally distributed model and I was given a new opportunity to be a business analyst. I had no idea what that meant or what we were supposed to do, but I was very lucky to have an information architect on my team who taught me how to talk to users, understand the problems they have, and truly try to solve them. I credit her with taking me under her wing and helping me get my footing in a brand new role and realm. It was incredibly kind of her. I've taken that lesson of her mentorship with me to try and do the same. I always want to share as much as I learn to help others grow and progress in their careers as well.

Can you share the details on your career path and what were the critical moments that got you to where you are today?

As I mentioned, my first role was as a business analyst and as I grew in my career I have had the opportunity to work in many different industries, including: criminal justice, telecom, government, financial services, education and healthcare. What’s interesting is the rules and regulations and the terminology of these industries are all very different but at the end of the day our role of building great products remains the same. To build great, and useful, products, you have to have an understanding of the environment the user is in, solving the problems they have, and then creating seamless experiences for them. If I look back at the critical points of my career, the first was when I started and the mentorship I received and the passion I found in figuring out people’s pain points. The second was when I started working in the world of startups. After working in a larger consulting organization (Publicis.Sapient) for many years, in 2016 I left to join a smaller, 15-20 person company called WiserTogether. It was an awesome opportunity and that’s where I became hooked on startups. Yes, they can be fast-paced and intense, but there is also so much opportunity to learn and grow and make changes that create better outcomes at a speed not possible at larger organizations.  

What is your current role and responsibilities?

I’m currently the Director of Product, B2B at Outcomes4Me.

Outcomes4Me is an AI-driven patient empowerment platform that helps cancer patients navigate their care and gain access to personalized treatment options. The company is on a mission to democratize healthcare by providing real-time, evidence-based clinical information to cancer patients, ensuring they can take a more active role in their own care. At the same time, we’re working to promote health equity by generating deeper insights that improve care, accelerate research, and lead to better outcomes.

I feel privileged and honored to be working at an organization that is working to empower patients, in our case cancer patients, with the tools and information they need to have a better journey with their disease. Every day I get to work with incredibly kind and talented people as we build product experiences for our patients while partnering with life sciences companies.

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position?

I think we all unfortunately know many people in our lives affected by disease and cancer and for so many it’s a very personal subject. I didn’t think I’d have the opportunity to take the skills I have and apply them to products that have the potential to help someone at a critical juncture in their life, but now I do. I feel honored to have this opportunity to help people at such an important and emotional time of their life and I try to do my best every day because of it.

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?

Be curious in both the role you’re looking for and the roles adjacent to it. For those looking to get into product, it’s so exciting to be able to partner with many departments in the company: user experience and research, design, engineering, marketing, customer success, and more. There is so much to learn from everyone. The best thing to do is reach out to people, understand their problems, and try to solve them. If you’re looking to move into a role that you don’t currently have, think about whether you’re in an environment where you could let others at your company, or even your manager, know. Many people are willing to help you in your career path if you let it be known and can help you work towards it. Voicing what you want is often the first step. And if the culture isn’t one that would embrace self-driven growth, it might be time to contemplate finding a place that would.

What are the most important skills that you need to do your job well?

To work in product leadership, you need to be curious, opinionated, able to use data (qualitative and quantitative), and open to ideas and feedback.

What do you find most interesting/rewarding about your work?  What’s the most challenging?

The most challenging thing about product is that everyone wants a new feature, button, or experience. Understanding what is the best thing for your users and being able to articulate and prioritize that as well as staying true to your North Star metrics are key to your success. It’s most rewarding when you’re able to watch users enjoy your product, and benefit from it.

What is your proudest professional accomplishment?

There are many I’ve been involved in which I feel lucky to, but one of the most recent was when I was working at my former company Evive. At the start of the pandemic, I worked with our team as we stood up a free public website evive.care with listings of all COVID-19 testing locations across all states in the country. Such a resource was not available at the time (this was prior to this information being available on Google Maps, etc.) and it was amazing to see our team work tirelessly to have this done in manual and automated ways simply for the greater good of society. I loved the pace we worked at and am honored to have launched such a product. 

Are you involved with any professional organizations outside of the company? Volunteer work?

While right now I’m very busy with my full-time role and family life, I have previously been involved in Women in Product and the Boston Product Management Association, and highly recommend them both.


Q&A

What do you enjoy doing in your free time?

I love spending time with my family and friends, especially my 4-year old who keeps me on my toes in the best way possible. I know as adults we’re trying to teach children things about the world, but sometimes I think the best lessons of kindness and honesty come from them. I am blown away by it every day.

How do you manage stress?

I love taking walks and spending time with family and friends to rest and relax.  It helps me recharge.

How many cups of coffee do you have in a day?

A cup of tea every day to wake up and then a coffee in the afternoon to enjoy the day.

What advice do you have for recent college graduates?

You can switch roles anytime or multiple times in your career. Try something, and if you don’t like it, try sometime else. Be curious about the work at your company and learn if that may be a fit for you!

About the
Company

Outcomes4Me is on a mission to improve health outcomes by empowering patients with understandable, relevant, and evidence-based information.

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Lead(H)er Profile - Carolyn Pampino, Vice President User Experience at SmartBear banner image

Lead(H)er Profile - Carolyn Pampino, Vice President User Experience at SmartBear

Open Jobs Company Page

Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Carolyn Pampino, Vice President User Experience at SmartBear.


Where did you grow up and how would you describe yourself as a child? 

I grew up in a suburban community just outside of Pittsburgh, Pennsylvania. I am the youngest of six kids, and yes, I still make the face I’m making in the picture, especially when I’m making an important decision. <wink> 

Early on, I was shy and perfectly content with creative projects or reading – until a YMCA opened a swimming pool. My parents were enthusiastic supporters. So much so, that when the YMCA ran out of money and could not finish painting the pool, my father collected exterior paint, rollers, and a crew of volunteers from the neighborhood. I have a vivid memory of standing in the corner with a paint brush while the volunteers bustled about with paint rollers determined to open the pool on time! The white was a funky beige, and the “black lines” were an eery blue, but the pool was painted! And it opened as planned! 

Holiday Hills YMCA. Circa ...too long ago to admit, but check out those bathing suits!  

That surge to meet deadlines has served me well throughout my career in tech! More importantly, the community felt like we owned that pool. After all, we made it happen! That spirit of coming together and allowing everyone to have a part in making something great happen has formed the basis of how I approach my job.  

What did you study in college and what was your first job out of school? 

I am the first in my family to graduate from college and work in tech. When I announced I wanted to study sculpture at Carnegie-Mellon, my parents didn’t know how to react. We were a blue-collar family, and Carnegie-Mellon is just as prestigious as an ivy league school. It would be great if I wanted to study something they considered practical, but art? Somehow, they managed to accept my ambition and support me. Then, I saw my first Pixar movie – Luxo Jr. At that time 3D animation was new, and I found myself spending time in the computer lab enamored by the idea. The processors were horribly slow, and there were very few classes, let alone a chance to major in computer animation. In my senior year, I went to a career fair and was recruited by an alumnus to join his software company in Boston. They developed high-end graphic design software primarily used for product packaging and high-end printing. They also rendered the design in 3D so manufacturers could test packaging ideas. Allured, I accepted the job and learned how to provide customer support to graphic designers. Hearing the customer confusion using our product helped me to develop empathy for their experience. 

My favorite getaway with friends at Carnegie-Mellon dreaming of our future.  

Can you share the details on your career path and what were the critical moments that got you to where you are today? 

My path wandered a bit as I explored different opportunities. It wasn’t long before I was recruited to quality assurance as a tester. Then a rare opportunity opened to sculpt for the New England Aquarium, and I leapt at the opportunity. We created a groundbreaking work. Instead of putting sculpted pieces into the aquarium, we built great structures to hold the aquariums. The effect was like walking through the Amazon Rain Forest.  We obsessed about the visitor experience as they moved through the aquarium from one exhibit to next – visitors entered into the Rainforest canopy seeing the birds flying among the leaves, next they were beside a rushing stream with three giant tanks of fish, turn right and come face-to-face with a poison dart frog at eye level in a tree! Looking back, this was my first lesson in experience design. 

It was a temporary job, and afterwards, I reentered the software industry testing fonts, then to complex document publishing software at Interleaf. It was here that I discovered user experience design, and then progressed through a variety of roles such as project management, product management, and engineering manager. I was a product director when Interleaf was acquired by BroadVision in 1999. I will never forget snowshoeing in Vermont and receiving a phone call to come back to Boston. We drove late at night through a wicked snowstorm. The next day, I was participating in the due diligence meetings with the executives. BroadVision was a Silicon Valley success story, and we were thrilled to be acquired by them. Our stock options took off, and I was a millionaire – on paper, as most of it wasn’t vested. I sold some, and I will always remember driving down US 101 in Silicon Valley, telling my stockbroker Vinny to “Sell, Vinny! Sell!” It sounds like a Danny DeVito movie, doesn’t it?  

After BroadVision, I joined Rational Software and soon after IBM acquired us. Rational was known for software development tools and its unified development process. A defining moment at Rational came when I was asked to do a “red thread.” The product managers were hearing our customers wanted integrated products. The “red thread” was intended to show how hard it was to accomplish a goal using more than one product. We changed the name to “green thread” to focus on the positive, or “to be.” If you have heard of the term “user journey,” this was an early form. In our case, we tracked the journey of a team of people working together to deliver software and identified the tools they needed to do their jobs. The shockers always came from counting the number of tools our organization was asking them to use, along with the gaps that prevented a team from using them efficiently. From then on, I was enamored by the storytelling that came with a user journey and the designing for an experience. I became a design manager, and then a director. 

Now my focus is creating environments where designers can thrive. I’m attracted to roles where I can transform a team and create a culture of collaboration with the peer disciplines. Afterall, it takes a team working together on journey to deliver great software, similar to how it took an entire neighborhood of volunteers to paint the bottom of that new swimming pool!  

What is your current role and responsibilities? 

I am the VP of User Experience Design at SmartBear. SmartBear creates products to help development teams deliver quality software. I view my responsibility as creating an environment where innovation can thrive. Our customers deserve to experience one SmartBear. This means our products must be easy to discover, try, buy, use, and support. It is my responsibility to make it easier for our product teams to work across boundaries, to think differently about the problem to solve, and to enable them to do their best work. This means we collaborate with our product peers and also our web, branding, sales, and support teams. In terms of the UX design team, I am hiring designers and writers to create a team and a design practice. All design practices come into play, such as visual design, interface and interaction design, user research, user experience design, UX Writing, and Technical Writing, along with the lesser-known practices of information architecture, content strategy, service design, design thinking, and design system design.    

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position? 

Definitely not when I first started. Initially, tech was my back up plan to fund my desire to sculpt!  Eventually though, I was lured into the excitement of creating software solutions to improve people's work lives. Then it became a mission finding ways to work with my peers to empower teams and deliver better software. As important as this all was, the pride in my dad’s eyes as I advanced propelled me the furthest. 

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals? 

I heard an expression used by TV writers: “Be good on the page, be good in the room, and be good to work with.” This translates perfectly to designers, and any discipline in my book. 

Designers today are more likely to be learning and growing in organizations that are supportive of their work. Designers and engineers are graduating with the training to collaborate as a multi-disciplinary team. However, not all organizations have this culture. This was the case for me. So, the first piece of advice is to ask questions about the culture before you join. Some companies are product-led with a strong emphasis on design, others want designers but don’t incorporate them into the culture in a healthy and meaningful way, still others diminish the role all together. A good designer knows how to ask open-ended questions and listen to the themes. Do that with your interview!  

Once in, be good on the page. Learn your products, your domain, and your design system if you have one. Most importantly, get to know your users! Make sure your designs meet the needs of your users while fitting with your brand and design system. Design and usability test with the people who will use your product when it’s released. Bring the best from the outside into your practice and hone your craft. 

Be good to work with. Get to know your peers on a personal level. Also involve them in your design decisions. Be prepared and ask meaningful questions. Collaborating to co-solve problems will improve your reputation as someone others want to work with. As a trained designer you have a unique advantage. You can use your powers of empathy to understand the pressures your peers face, and then use your creativity to solve their pain points with a design method. By this, I mean there are many situations where the team you are working on is struggling. In that moment, do you know a design method that can help them solve the problem? Try to convince them to do it together, or just do it yourself and present it back to them. Sometimes it works on the first try, sometimes it doesn’t. But try – with moderation. Go too far and you are no longer good to work with! So, try to balance it by reading the response. Are they open to your suggestions because you are winning them over or are they turning away? Through it all, you are gaining skills in problem solving, collaborating, influencing. When it works, it not only wins trust, but it also shows leadership. You willingly leaned in, made a recommendation, and helped advance the team’s mission!  

Be good in the room. Throwing your peers under the bus in meetings is a bad way to advance your career. A friend once taught me the expression of being “dead right.” It means you are right and you’ve angered everyone around you to the point that they no longer listen to you. Don’t do that. 😉 If you are good on the page and are appropriately involving your peers as you evolve your designs, team meetings and reviews will go much smoother. Learn how to present your work and to listen to feedback. This may be one of the most important skills you can hone – how to present a design and direct your audience’s attention to where you need their feedback. David Royer and Suelyn Yu offer good advice for presenting a design in this blog

Read obsessively. Not just design blogs & books, but business blogs and books, too. It’s important to learn the language of the business to align your work with business outcomes. Learn about leading change, about influencing without authority, and apply one lesson at a time. Then, when someone opens a door of opportunity, run through it with all your glorious superpowers!  

What are the most important skills that you need to do your job well? 

See the previous answer. 😊 Design can be a misunderstood discipline. Many people assume that designers make something look good, when in fact, good design defines how a product works and the impression it creates in the mind of the user. This involves uncovering what people need, help defining the problem to solve, then solving it by working through a strategy, creating, and testing prototypes, and eventually nailing the screen layout and visual impact. Educating our peers, winning trust, speaking the language of business, and gaining trust are fundamental to your success.   

What do you find most interesting/rewarding about your work?  What’s the most challenging? 

A designer's job is to create solutions that make people's lives better. Studying people is fascinating.  Ideating with a group of people to solve human problems is energizing. Making that solution easy to use and aesthetically beautiful is both frustrating and rewarding. It is incredibly difficult to make hard tasks easy. It is equally challenging to scrap a design and start over. But when you observe those people take delight in using your solution, it is worth it!  

There are many situations where the different disciplines on a team haven’t figured out how to work together. Often, design skills are misunderstood, and designers are brought in too late. This creates frustration for the designer and places an unfair burden on the product managers and developers to do the work a designer could have done. When you get the mix right, the designer thrives, and the product manager and developer jobs get easier. You can feel and see the stress levels go down. Together, they build momentum and the solutions they deliver to their customers are better as a result. I find this incredibly rewarding. It’s human nature to rely on what you know when you are under pressure. Introducing change and convincing teams to try working differently can be challenging. So, I look for opportunities and coach my designers to look for opportunities to lead. There is always a moment where the designer can lean in with a proposal to solve a problem. Once they do, trust builds, and eventually the designer can find themselves exactly where they belong – as a trusted leader on the team. 

What is your proudest professional accomplishment? 

I have a couple. Interleaf, 1999. Uniting as a team to have Interleaf acquired for $851 million was an amazing experience. We were a small but united team that managed to get noticed by one of the early high-flying internet companies, BroadVision. It was thrilling, and that’s what created the “Sell Vinny sell” moment on US 101. Then about a decade later, the scenario work at IBM Rational became the underlying thread that drove a line of products. By driving integrations across three products, we managed to triple their revenue.  The value proposition is what was implemented, tested, marketed, and sold. Again, a team of people came together and united around a mission. Moments like these give me goose bumps. My last one was at my prior company. We had groups of designers who were brought in by acquisition, who hadn’t been treated appropriately for their skills. The same could be said for the technical writers. By the time I left we were a united team, and the individuals were thriving and growing. I know I left them in a better place than where they were when I met them. It’s now my newest mantra: If I were to leave today, are they better off than how I found them? This drives me each day. It’s less about perfection, and all about incremental improvement each day to enable designers to do their best work. 

Are you involved with any professional organizations outside of the company? Volunteer work? 

I try, but honestly, I leave it all on the “working field.” I do donate food to a local food pantry and the Newton Freedge. The Freedge is a 24/7 pantry that anyone can donate or take food from. Food security is something that is personally important to me. It feels good to stock the shelves and the fridge with food people need.  


Q&A 

What do you enjoy doing in your free time? 

My Cardigan Corgi’s hypnotize me into giving them most of my free time. They make me smile, play, and take long walks. I’ve had other dogs, but the Cardigan Corgi is different. It is as if they have hypnotizing powers, and before I know it, I am doing exactly what they want me to do. Their full names are Shapeshifter Sam, and Sookie TruBlu, but they answer to Sam, Sookie, and ‘treato!’ I could fill this entire article with their stories.  

I’m currently tending to a small vegetable garden – I have seven varieties of potatoes in grow bags. I can spin quite a tale about the virtues of growing your own potatoes. Really, home grown potatoes are better, just like home grown tomatoes are better. Seriously. I haven’t bought a potato in three years. And the varieties you can grow are so much better than the store offers. All it takes is a growbag. 

I still pick up a hammer and chisels to sculpt alabaster when I can. Right now, I’m creating two clay sculptures for a friend from college. I gave him a sculpture when he graduated, and recently a new cat knocked it off the shelf. He contacted me asking if I could recreate it! The first led to a request for a second, new piece that includes his children. Here’s a photo of the original, and the recreated version still in “draft” form.  

How do you manage stress? 

See my free time. 😊 I have many approaches to suit my mood and energy levels. The fun I have in my free time is my best stress reliever. When that isn’t enough, I practice yoga, cycle using the app called Zwift, or solve puzzles. 

How many cups of coffee do you have in a day? 

One 

Any book or podcast recommendations?

Professional: The Outward Mindset: Seeing Beyond Ourselves. The Arbinger Institute. This was introduced to me by a peer, and it’s a fantastic example of how approaching situations with empathy can lead to extraordinary outcomes. The book is filled with stories which makes it an easier read and inherently creates an outward mindset in the reader. For example, one story involves a police team raiding a home. Amidst the chaos one officer notices a screaming baby in his mother’s arms and warms a bottle of formula to comfort the child and the mother. They were a group that took a very different approach to their role in their neighborhood. We could use a lot more of that now.  

What advice do you have for recent college graduates? 

For design graduates, I have two requests.  

First, apply to the appropriate position for your level. I don’t know how many new graduates I see applying for senior and even director positions! The second I see that, you’re out.  

Second, your resume and portfolio are your key to the interview. Apply your design process to creating these two important representations of your talent. The care and attention you give to these two artifacts speaks volumes about you as a designer. Start with empathy for the hiring manager. Hiring managers have open positions – this means they are understaffed, which means they're incredibly busy! They receive upwards of hundreds of applicants. How are you going to catch and hold their attention? What do you want them to think, feel, say, do when they look at your resume? Now design it for the right outcome... which is to open your portfolio.  

Now that they see your portfolio what do you want them to see and do? Take everything you know about design into account. What is the ‘gestalt’ impression. How about the visual hierarchy? What story are you telling us? When you only provide images of your work how likely will they understand what it is, what your contribution was, and whether it solved an important problem or not? The details matter! Please take the time to explain your process, the key decisions you made and why you made them, whether the design succeeded at the intended goals, along with the key learnings.  Consider choosing one case study and explain the full process. This is more valuable than a bunch of images with no words. The designer who can tie their solution back to the user problem and back to the business goal is that one that impresses the most. And don’t password protect it! I pass over applicants simply because they added a password to a portfolio. I’ve adopted this because of the number of passwords that didn’t work!  Interviewing is labor intensive. Adding any friction to that process, such as a password on your portfolio, could lose the chance of an interview. So, apply the design process and win yourself that job!  

About the
Company

Smartbear's tools are built to streamline your DevOps processes while seamlessly working with the products you use – and will use

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Lead(H)er Profile - Alison Durant, Chief Marketing Officer at EngageSmart banner image

Lead(H)er Profile - Alison Durant, Chief Marketing Officer at EngageSmart

Open Jobs Company Page

Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Alison Durant, Chief Marketing Officer at EngageSmart.


Where did you grow up and how would you describe yourself as a child? 

I was born and raised in Massachusetts and was a competitive sailor growing up. Sailing has always been a huge part of my life and has shaped who I am today. I was only a few months old the first time my parents took me on the water, and I began competing as soon as I could hold a tiller.

I was and still am extremely competitive and learned a lot of valuable skills competing in a sport that requires both quick-thinking and a true partnership with the rest of the crew. Sailing is a sport dominated by men, so what I lack in strength and size, I make up for in skill, determination, and communication skills. All of this has translated over into my professional life and success today.

What did you study in college and what was your first job out of school?

I studied Campaign Management at Franklin & Marshall College and landed my first job as an Account Executive at an agency focused on medical devices and diagnostics. I took on several public relations agency roles before moving into a leadership position at Horn Group where I spent ten years building the Agency’s Boston practice, shaping the external communications programs for startups and what are now some of the largest companies in enterprise technology. PR requires both quick and strategic thinking as well as close collaboration with a variety of personalities in high-stakes scenarios - similar to the skills required to win on the racecourse.

Can you share the details on your career path and what were the critical moments or turning points that got you to where you are today? Was there a person who influenced and/or inspired you along the way?

A real pivot point on my professional journey was the shift from client service and strategic communications on the agency side to in-house marketing. Suddenly, I had one client but more stakeholders than ever to consider in day-to-day operations. When I joined Endeca (acquired by Oracle), there was a very palpable sense of building something great together with some of the smartest people I’ve ever worked with. My Endeca colleagues have gone on to build amazing new companies and to take leadership positions in formidable enterprises. It didn’t feel like a turning point at the time but looking back it very clearly stands out as the point when I realized that the companies and teams you surround yourself with matters. We should be asking ourselves - are you inspired and challenged to think bigger by your colleagues? Do you feel supported by your team to try new things and take risks in the spirit of innovation and competitive advantage? You can say you are going to do all those things, but without an atmosphere of mutual support and good humor at work, things easily fall into status quo. 

Sabrina Horn was certainly a big influence early in my career. So much of what she embodied as an authentic leader, confidant to CEOs, and mentor to her teams still shapes the way I view my work and my role as a leader. Authenticity is talked about a lot because it matters. Sabrina walks the walk and during the decade I spent at Horn Group, she inspired her people to bring not only their best selves to work, but their whole selves. I strive to do the same thing for my peers and my team. We can’t possibly be as innovative, competitive, or productive otherwise.

What is your current role and responsibilities? 

As the Chief Marketing Officer, I oversee all aspects of EngageSmart marketing. This means wearing many hats, but my primary focuses are building our corporate brand identity and supporting our solution marketing teams in their efforts to build and grow awareness in the markets they serve. 

Much of the value in EngageSmart is in the strength of our vertically tailored solutions: SimplePractice, InvoiceCloud, DonorDrive, and HealthPay24. While these solutions have been connected for several years, the EngageSmart brand is fairly new, so a big priority for me is to help build awareness for and understanding about Corporate brand both internally and externally. Another, and equally important, priority is to grow our Enterprise business. Each vertically tailored solution serves a distinct audience (municipal tax and utility billers; enterprise nonprofits; and healthcare and hospital systems).

In addition to working with EngageSmart leadership and the executives of all our solution groups, I partner across the organization with key functions like HR to drive internal communications and employee engagement, corporate communications, content marketing brand identity, public relations, social media, and so much more.

I joined EngageSmart in the fall of 2020 as the company’s first marketing leader and less than a year later, we took the company public. Many critical functions worked to together to ensure our teams were operating in complete alignment required to be successful as a public company. This was a huge undertaking, and one that I’m very proud to have been a part of. But in a lot of ways, the real work has just begun—we have a whole new set of audiences to engage. It’s exciting, and it’s going to require a lot more people to help us continue to develop our amazing solutions and continue to delight our customers and their clients as we grow. Did I mention we are hiring?!

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position?

As a competitive sailor, I grew up on teams and have always enjoyed working with others. I knew I wanted to be around smart, creative thinkers and doers. People with vision who also put in the work to make it happen. Marketing and strategy appealed to me, but I’m not sure I understood what it entailed until I found myself doing it. Again, it was the people and learning opportunities that I sought out first; the actual subject or area of the work came second to that. I think it's extremely important to be open-minded when entering the job market because you never know when new opportunities will present themselves. I entered the working world and joined an agency following college graduation based on a relationship I had in the sailing world.  

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals? 

In terms of long-term career goals, I can’t stress the importance of working with people you can learn from. Much like sports, you only get stronger, smarter, and more skilled by playing with folks who excel in areas you don’t. Also keep in mind that if you have joined the right team, you bring a unique point-of-view and skillset to the job. You want to be around people who inspire you to learn and grow, but who also support your curiosity and build the confidence of the team in positive ways.

Spend time considering who influences you. Is there a mentor or two you can consult and strategize with? Will they also be your champion in the workplace? Do you have confidence among your peers that you can turn to on the hard days? Finally, who are you mentoring and championing for? A solid network is critical to success. I’m not just talking about connections in positions of influence; I’m talking about people you can directly learn from and vice versa in very tangible, productive ways. Who you surround yourself with on a daily basis, how you treat them, and how they treat you can make a much bigger impact on your career path than simply a few powerful contacts. I also believe that our networks make for a happy work life—something we all need, or the journey just isn't’ worth it. 

EngageSmart’s company culture really stood out to me when I was looking to make the next step in my career. EngageSmart has leading products in the markets our solutions serve, delighted customers, and most important to me, employees who were excited to come to work. I knew I wanted a position where I could grow as a person, and where I’d be supported in building something new. I think most people want to make an impact in some way and to also be impacted positively by the people they work with – I found this at EngageSmart.

What are the most important skills that you need to do your job well?

The ability to understand, and connect with, your audience cannot be understated. On a day-to-day basis, I may be connecting with four or five different audiences. It can be easy to over-simplify the audience groups into internal and external, but if it’s internal—which solution am I connecting with? And from an external perspective, am I connecting with clients? Shareholders? What message do I want each audience to walk away with? What do I want them to do? Understanding and connecting with your audience is a critical foundation of marketing and communications in any organization.

Adaptability and creativity are next on my list. We live in a time of rapid change and growth, what may have worked well six months ago can suddenly stop working. Having the ability to think outside the box, quickly problem solve, and adapt to our ever-evolving environment is key. 

Finally – the ability to stay focused. As a leader overseeing multiple solutions, I often find myself being pulled in different directions with competing asks—which could lead to distraction and stalled execution. However, staying truly mission-focused allows me (and my team) to quickly weed through the work that may not directly align with our strategy and goals—and focus on what does.

What do you find most interesting/rewarding about your work?  What’s the most challenging?

I touched on this a little bit, but culture at EngageSmart is extremely important — and working with such dedicated, fun, and supportive people really is rewarding. Our leadership team has worked hard to build an inclusive work environment where employees are excited to come to work.

Given that the EngageSmart brand is still relatively new, one of the biggest challenges for me as a marketer is around sharing the overarching brand story. It takes a lot of thoughtful work at the strategic level, but our biggest challenge (and of course, opportunity) is building understanding and advocacy from employees throughout the organization. We’ve got distinct solution groups under the EngageSmart umbrella that have established brands that are known and loved by their respective customers and employees. I need to partner with the solution teams and help preserve the enthusiasm for each of these while also building equal understanding and excitement around our corporate brand. 

One thing I love about marketing is the ability to craft a brand’s identity and connect with customers in meaningful ways. The good news is that every member of our team is united behind the company ethos to make people’s lives easier with our products and solutions. At EngageSmart, we believe that every time someone says “it shouldn’t be this hard,” they’re right. Whether it's paying bills or booking an appointment with a therapist, our jobs  help make our customers’ lives easier. That is really gratifying.

What is your proudest professional accomplishment?

There are two separate things that come to mind. First, I love helping employees grow within our organization, and to develop their own career. I’m proud to be a mentor to some of the amazing former colleagues. It's very rewarding to support these talented individuals and watch them achieve their goals, many of whom have moved on to run their own marketing departments and build their own new teams.

I’m also extremely proud of our team’s work taking EngageSmart public last fall. Leading the marketing efforts for our IPO, alongside colleagues in Finance, HR, Legal, Operations, and more was both challenging and rewarding. Working together as a newly established team to become a public company was an important step in our company’s growth, and I’m proud to have been a part of that. With amazing solutions and a team of top talent, I’m also very excited about the next stage of growth for EngageSmart.

Are you involved with any professional organizations outside of the company? Volunteer work?

As I’m sure you can tell, sailing has always been a huge part of my life, and still is. I’m on the leadership council at the Buzzards Bay Coalition, as well as the Board of Directors for the New Bedford Yacht Club. I think it's important to find meaningful causes outside of work, so I’m fortunate to be a part of these organizations and their missions to support the Southcoast of Massachusetts. I have also helped fundraise and plan events for the Community Boating Center of New Bedford, as well as the Lloyd Center for the Environment. It’s been great giving back to the community that introduced me to my favorite sport and hobby.

What do you enjoy doing in your free time?      

We are an active family and I spend a lot of time outdoors with my husband and our two kids. We split our time between Sunapee, New Hampshire and Dartmouth, Massachusetts and spend a lot of time sailing together in the summer and skiing in the winter. It’s great to share sports with my family that we all enjoy and can do together. The newest addition to our family is an Australian Shepherd, named Rhea, who ensures hiking is a part of every-day life,    

Both my son and daughter are involved in high school sports and watching their games is priority for me. Not sure the kids feel the same way! Being the parent of a pitcher and a goalie is tough stuff! 

I’m so fortunate to work for a company that prioritizes health and well-being and encourages employees to take time with their family. There is a fair amount of data that shows that people are not taking enough vacations even when they have enough paid time off. I try to lead by example and encourage my coworkers and employees to do the same.

How do you manage stress?

Getting outside is my favorite way to manage stress. Whether it’s a dog walk or a quick trip on the boat, the fresh air is renewing. I also love working in the garden – pruning and weeding are little projects that provide instant gratification. I’m totally clueless, but herb gardens are hard to mess up! 

I love talking to my kids about their day, their games, their goals – even weekend plans. I try to set evenings aside for that stuff, and while I can’t say it happens every night, it does help me stay rooted in what really matters.

How many cups of coffee do you have in a day? 

Ha! A lot – probably eight. I also am known to enjoy a box or two of candy during the day. Hot Tamales, Good-n-Plenty and Peeps!.

Any book or podcast recommendations?

I highly recommend reading Make It, Don’t Fake It by Sabrina Horn — it's one of my favorite books. Sabrina is one of my mentors, and I worked with her for about ten years. “Make It, Don’t Fake It” is something I strive to live by in my professional and personal life. An enjoyable and sustainable workplace needs to be driven by authenticity, as does any marketing strategy or business plan designed to put customers first.

What advice do you have for recent college graduates?

Network as much as possible! People are often hesitant to reach out because they don’t want to seem annoying or assume they don’t know anyone who can help them. Your network is much bigger than you think — you have friends, family, coworkers, and alumni networks. It may surprise you how willing some people are to help. Networking is more than just looking for job opportunities. It's about building relationships and maintaining connections for the future. 

And, when you’re out there interviewing, I think it's extremely important to focus on the company’s mission and try to envision yourself working there. Hiring is a two-way street — while the company is interviewing you, you should be making sure the company is a good fit for you. Pay attention to how companies present themselves publicly. Do their values align with yours? How do they support their employees? How real is the person interviewing you willing to be about the challenges of the job? Consider the opportunities it presents. Ask hiring managers what they do outside of work—and how much they know about their colleagues’ own passions and pursuits. That can tell you a lot about the people you’re going to be working with, and in turn, the culture of the company itself and how it supports the whole selves of its employees.

About the
Company

EngageSmart is a leading provider of vertically-tailored customer engagement software and integrated payments solutions.

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Lead(H)er Profile - Ashwini Tumne, VP of Engineering at Everquote banner image

Lead(H)er Profile - Ashwini Tumne, VP of Engineering at Everquote

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Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Ashwini Tumne, VP of Engineering at Everquote.


Where did you grow up and how would you describe yourself as a child?

I was born and raised in a small town, near Mumbai in India. As a somewhat introverted child, I had always been a curious, inquisitive child who was known for engaging with close adults around me in a wide variety of conversations. Kudos to my parents for instilling the habit of reading and always encouraging that inherent curiousity towards broadening my sphere. This in turn drove me towards science and space. In my early years, I had wanted to be an astrophysicist with a goal of becoming a NASA scientist.  

Ashwini Tumne EverQuote

What did you study in college and what was your first job out of school?

When I was in high school, I had an opportunity to write my first program, in BASIC! This drove me towards the field of computing and I ended up with a bachelor's in Computer Engineering and later, Masters in Computer Science from Northeastern University. My very first job happened in a year between my two degrees when I worked at a Naval Engineering company and wrote ship loading software for huge cargo carriers.  

Can you share the details on your career path and what were the critical moments that got you to where you are today?

In the first few years after my college, I was doing deep software development on a variety of platforms and stacks. I experimented with different programming languages and ultimately was focused on multi-tier architecture software. The opportunities I had along this journey taught me a lot about designing consumer facing software and also internal business critical platforms. 

Having this experience and background, I was offered a role at an almost startup small company called Grasshopper. This was a new chapter in my journey. At Grasshopper, I learned about telecom, user experience, usability, API development at scale, payments landscape and so much more. Being at a small company and fortunate enough to have a great leadership team, I was offered my very first management position. The chasm of moving from an individual contributor to a people manager was deceptively small at first. But took on that challenge and never looked back. I was now entrusted with not just my work, but also the work of my team. I helped grow the product and team, oftentimes with constraints and numerous challenges along the way. Learned valuable lessons in change management at every level - infrastructure to people organization as the company was acquired and ended up as a growth product at LogMeIn (now GoTo). Another pivotal moment for me was being part of a tiger team tasked with innovating our way towards the next product. Four months that I spent in the incubation bunker was a crash course in product-driven development with the bonus of actually bringing this vision alive and going to market with it. 

After 7.5 years at LogMeIn, having led global engineering teams, and never shying away from new and unknown areas and situations, I started stagnating slowly. When I was reached out by the EverQuote team, I leaped at the opportunity to lead the Ad Tech engineering team, which represented a completely new domain for me. 

What is your current role and responsibilities?

Today, I lead and drive engineering involved in Consumer Engagement and Experience at EverQuote, both of which are crucial backbone for delivering value to our shoppers by empowering them to protect life's most important assets, while providing the value add to insurance providers. My role is to help set the technical execution strategy for the mission and vision while upleveling teams and platforms. I execute primarily on the four dimensions - people, product, platform and process. All four pillars get continuous assessment and improvement to deliver and perform at their best. 

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position?

My personal north star has been continuous learning, challenging and upleveling myself and others while helping build systems that make a difference, at scale. At every crossroad I had taken up opportunities and sometimes crafted them up to lead me towards that north star. So, I continue to be able to do that and I can say this is where I want to be. However, I am not tied to a specific rigid ladder or a path in my mind either. 

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?

In my perspective, if a person wants to move the needle on their career paths, first off, they need to be open to ideas and change. Oftentimes we have prebaked notions and biases about various topics in this field and they end up limiting us. Invest in people and strive to lead and be part of a healthy team. Take time to understand the company’s value streams and follow the impact areas to help figure out your next steps. Always endure to understand and explain the ‘why’ behind the product and engineering decisions to be able to deliver on either or both. Stakeholder management is sometimes the most essential function a leader can play. And last one, incident management is an underrated team building activity and getting involved always offers a wealth of information! 

What are the most important skills that you need to do your job well?

Leading and driving teams towards their short and longer term goals while navigating through a changing environment.

What do you find most interesting/rewarding about your work?  What’s the most challenging?

Successfully reacting to ever changing landscapes, reaching team milestones, delivering value to stakeholders and helping folks around me scale themselves up. 

What is your proudest professional accomplishment?

Honestly, it's hard to select just one. When I see the impact of my work by means of folks stepping up and growing their chosen paths, high functioning teams producing sustainable systems and platforms that serve their purpose and some more. Ultimately seeing business creating value and impact in the lives of others using these, it is an ultimate gratifying and proud moment.


Q&A

What do you enjoy doing in your free time?

Spending time with family, taking walks with my husband, reading, traveling, and exploring new places. 

How do you manage stress?

Break out my paper to-do list to write all that's on my plate, then prioritize and make it manageable. Walk, meditate, and listen to music.

How many cups of coffee do you have in a day?

1-2, but I love having herbal teas and Indian chai! 

Any book or podcast recommendations? 

Books - No Rules Rules, Lean In. Podcasts - MarketplaceIdeaCast, InfoQ

What advice do you have for recent college graduates?

Take time to learn and be unafraid of new avenues ahead. Keep challenging yourself and others around you by asking the hard questions. 

About the
Company

We are the largest online Auto Insurance marketplace in the U.S. We're helping end distracted driving with our safe driving app, EverDrive.

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Lead(H)er Profile - Christine Ho, Senior Director, Technical Programs Lead at Motional banner image

Lead(H)er Profile - Christine Ho, Senior Director, Technical Programs Lead at Motional

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Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Christine Ho, Senior Director, Technical Programs Lead at Motional.


Where did you grow up and how would you describe yourself as a child?

I was born in New Jersey, but was raised in Hong Kong and Tokyo. My parents immigrated to the U.S. from Hong Kong, my sister and I are first generation Americans. The global nature of my upbringing made me culturally aware at a young age that there was much more to learn. This translated into my career as an engineer. I've always had a sense of curiosity and wanting to problem solve, whether it was puzzles, clocks, door knobs, or light switches.

What did you study in college and what was your first job out of school?

I received a BS in Material Science and Engineering from Rutgers University and a Masters in Systems Engineering at Stevens Institute of Technology. Initially, I was interested in learning more about materials, but that passion evolved into wanting to make a greater impact on society. My first job after college was the Engineering Leadership Development Program (ELDP) at BAE Systems. It’s a rotational program to see different parts of the corporate world.

Can you share the details on your career path and what were the critical moments that
got you to where you are today?

There have been many moments but a few that stand out to me:

  • At BAE Systems, I had the opportunity to see different life cycles of a program: Final test set-ups (understanding the customer needs to develop something to be easy), to mature products, to continually integrate them.
  • At Gogo Business Aviation, I leveraged system engineering foundations to accelerate architecture and design for in-flight connectivity and entertainment systems.

I would say the most critical moment is what got me to where I am now at Motional. I realized I wanted to diversify my skill set and jump into an industry, autonomous vehicles, that I had zero exposure or prior knowledge about. I took a leap of faith into this world of cutting edge technology - it’s been an exciting journey.

What is your current role and responsibilities?

I serve as the Technical Program Leads at Motional where I oversee a large group of talented technical programs managers. We’re focused on bringing our fully driverless (SAE Level 4) robotaxis to market, starting in Las Vegas in 2023.

Looking back, is this where you thought you’d be professionally? Was it always your goal to be in this position?

I’ve always known I’ve wanted to make an impact on people's lives and be surrounded by a strong team that’s passionate about our mission.

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?

I’d say to never give up on your goals, stay focused on what excites you. While mentorship is frequently discussed, it’s not always easy to enter into that type of relationship. Even without a formal mentor, you can still learn from those around you. Find colleagues or leads who you work with and pick one or two attributes you would like to adopt and use day-to-day. I’ve implemented habits that I admired in leaders
throughout my career.

What are the most important skills that you need to do your job well?

In such a dynamic role, it’s critical to:

  • Listen to other people's ideas
  • Be attentive and present in the conversation
  • Obsess over the details
  • Trust your colleagues and your strategy

What do you find most interesting/rewarding about your work? What’s the most
challenging?

At Motional, I’m really fortunate to work with an incredible group of people who have an
unwavering focus on our mission, making driverless vehicles a safe reality.

The most challenging aspect is what we’re building, the technology, level 4 autonomous vehicles. This is one of the most challenging engineering projects of our lifetime. It’s rewarding to work through problems that have never been solved before and see our vehicles hit the roads. AVs will significantly improve transportation for communities around the world, and we’re responsible for making that a reality.

What is your proudest professional accomplishment?

Delivering products to market. At Motional, I worked on the team that was responsible for reaching a significant technical milestone - fully driverless operation in 2020. There are very few companies in the world capable of this, and we’re one of them.

Earlier in my career at Gogo Business Aviation, I helped to deliver a modular platform that is now known as the AVANCE Platform. I was involved in the process to certify the product to meet DO-254 Design Assurance Level (DAL) D which was a first for the company at the time!

Are you involved with any professional organizations outside of the company? Volunteer
work?

Professionally, I’m part of SWE, Society of Women Engineers. In my personal life, I’m an avid golfer and am a part of the LPGA Amateur Golf Association. 


Q&A

What do you enjoy doing in your free time?

As I mentioned before, I’m an avid golfer.

How do you manage stress?

Going for a walk with my partner and dog around Boston’s North End, and of course, golf.

How many cups of coffee do you have in a day?

Depending on the day, 1 to 3 cups.

Any book or podcast recommendations?

Anything Malcolm Gladwell - Blink or Outliers.

What advice do you have for recent college graduates?

Don’t compare yourself to others. You are a unique individual on your own adventure: you get to define, learn, and iterate through every step in your career. Also, you are your own biggest cheerleader and advocate. This advice is especially relevant for women who often aren’t as vocal in advocating for their advancement, whether it’s taking on a new project, position, or raise.

About the
Company

Motional is making driverless vehicles a safe, reliable, and accessible reality.

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Lead(H)er Profile - Erica Jenkins, Chief Product Officer at Crayon banner image

Lead(H)er Profile - Erica Jenkins, Chief Product Officer at Crayon

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Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Erica Jenkins, Chief Product Officer at Crayon.


Where did you grow up and how would you describe yourself as a child?

I grew up just outside Rochester, NY about an hour from the Canadian border.  As a child I was into several sports, including horseback riding and I loved Summer camp.  My teachers would say I was very bright but a little too social so I probably talked to my friends more than I should have!  My folks would say that I asked a lot of questions which has proven to be a valuable personality trait in my career.  #curiosity 

Spending time with my daughter supporting her passion. We travel often for her shows around the SE US. 

What did you study in college and what was your first job out of school?

Looking back I wish I’d known more about technology and computers but it just wasn’t taught much in the early 1990s, especially to females. Traditional sciences were a big interest to me so I entered college as a biology major.  Once I realized this wasn’t a true passion, I swapped over to business studies with a focus on PR.  If I’m honest with myself, I learn best by “doing” and shadowing others.  I wasn’t sure what I wanted to “grow up to be” so I took a break.  After a short self-reflection, I jumped into a real estate career.  It was pre-social media but I quickly learned how to become a marketing lead engine with content and engaging on forums.  This digital transformation of marketing tactics and consumer communication ignited my entrepreneurial spirit.  

Can you share the details on your career path and what were the critical moments that got you to where you are today?

As I mentioned, in the mid-2000s marketing tactics and consumer communications with social media emerging created a pain point for me as a business owner.  I needed time back and the idea for my startup was born.  I didn’t realize it at the time but social media management to publish, drive engagement and measure the impact was emerging as a big business.  Expion was competing with Hootsuite, Sprinklr, Sprout Social and many others.  Learning enterprise marketing challenges was extremely valuable for me to see how large corporations were in need of so many different types of collaboration tools.  The knowledge I’ve gained from working with large global brands, social media developer partnerships and the many brilliant engineers I’ve had the pleasure of working with has been invaluable. 

Another aspect of what I’ve learned is growing a team and having empathy for employees.  My hope is any of my old colleagues would want to work for me or with me again.  People matter far above building software.  

What is your current role and responsibilities?

Chief Product Officer at Crayon.  We’re growing our team to unlock competitive intelligence to infuse competitive awareness for positioning, sales enablement, and overall stronger business awareness of competitive moves in the market.  

What is your proudest professional accomplishment?

Bootstrapping a startup and successfully getting acquired.  

Last International Trip on March 11, 2020- I was the only person in my cabin to London

Are you involved with any professional organizations outside of the company? Volunteer work?

I join a few product management mentoring Twitter Spaces to help share my journey and the executive viewpoint of skills and attributes I value in a product manager.  Volunteering is scattered amongst my daughters' school events when I can.  I need to lean into joining more organizations to learn or contribute my experience to my Personal development goal for 2022. 


Q&A

What do you enjoy doing in your free time?

In season, I love to spend time on my boat with friends.  I’m always reading tech and business news to keep a pulse on the latest and greatest for work and my own knowledge.  Working at a growing series B startup keeps me busy so a quiet Saturday with some Netflix is my time to chill out and not feel guilty for being lazy.

I enjoy getting out on the boat to spend the day on the water and occasionally drop a line! 

How do you manage stress?

Great question, one day at a time!  As a single Mom, I have to really try hard to make time for myself.  Walking outdoors helps me de-stress.  An early morning routine I’ve tried to adopt during the pandemic is listening to a guided meditation for 20 minutes before I start my day.  It helps with centering my thoughts to start the day.

How many cups of coffee do you have in a day?

2 cups before 10am.  One to get me through carpool, the other to get me through my email backlog. 

Any book or podcast recommendations?

Radical Candor by Kim Scott

What advice do you have for recent college graduates?

Be curious.  Coursework can only teach you frameworks in technology.  The more you dig into a business problem, the more you understand and generate empathy about how to solve it.

About the
Company

Crayon’s award-winning competitive intelligence platform helps your organization see and seize opportunities so you can create a sustainable business advantage.

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Lead(H)er Profile - Laura Miyakawa, VP of Engineering at Reprise banner image

Lead(H)er Profile - Laura Miyakawa, VP of Engineering at Reprise

Open Jobs Company Page

Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Laura Miyakawa, VP of Engineering at Reprise.


Where did you grow up and how would you describe yourself as a child?

I grew up just outside Atlanta.  I was a nerd in many senses of the term.  I got a high school letter for the math team.  (I never got the letter jacket to go with it.)  But, I was also a chorus nerd - I was in the madrigal choir, dressing up in full regalia - and a community theater nerd, playing various Cratchet children in the annual production of A Christmas Carol (though never Tiny Tim).

What did you study in college and what was your first job out of school?

I went to Carnegie Mellon University, because it was a great school, but wasn’t just a tech school.  I loved hearing music from the practice rooms echo across campus as I walked home from my labs.  I studied electrical and computer engineering, but my heart was always in signal processing.  The math is intense, and getting your brain to think in both time and frequency spectra was loopy.  

I wasn’t really sure what I wanted to do coming out of college, but since I was a good student and enjoyed TAing a class, I thought I should stay in school, get a PhD and become a professor.  When I finished up in Pittsburgh, I went straight to MIT to start graduate school.

Can you share the details on your career path and what were the critical moments that got you to where you are today?

I realized pretty quickly that I hadn’t considered the research responsibilities both of graduate school as well as becoming a professor.  I had a conversation with my advisor that went something like this:

Me: What is it about speech recognition that gets you up in the morning?

Advisor: It’s such a hard problem…

Me: <nodding emphatically>

Advisor: I’ve worked on it for 25 years, I could work on it for 25 more.

Me: <thinks to myself “that sounds like a life sentence”>

I left graduate school the next year (technically it was a leave of absence, but I doubt they’d have me back at this point), looking for an opportunity to have an impact but on MUCH shorter timelines.  I joined a management consulting firm.  

I loved working with smart people on tough projects.  I had the opportunity to work in Australia for a couple of years (highly recommended).  But it also felt like it wasn’t quite what I wanted.

I found myself in engineering leadership at a startup after a few other stops along the way, and it just felt right.  I was back working with the technical folks I’d learned with in college, but I could bring the business acumen I’d developed in consulting.  

What is your current role and responsibilities?

I’m the VP of Engineering at Reprise.  I define my role as being responsible for the People, the Process, and how we work with the Product team.  I have had the privilege of building the engineering team here at Reprise, and I’m so proud of what this team has accomplished.

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position?

Definitely not.  It felt like a slow series of steps.  At some points, it felt like it would be the slowest process of elimination to figure out where I belonged.  But at each step, I learned more about what motivates me (team) and what orgs I fit well in.

What are the most important skills that you need to do your job well?

Listening, enthusiasm, authenticity, and an eye for detail.  I’m not even close to the most technically proficient member of the team, but I know how to get things done - how to organize technical resources to get the best outcome.  I care about the members of my team, and I’m always trying to find the solutions that best suit my team’s needs and meet the needs of the business.

What do you find most interesting/rewarding about your work?  What’s the most challenging?

The answer is the same: the rate of change is both challenging and rewarding.  I love being in a small agile organization that is growing.  There are new problems to solve every day.  The challenge isn’t easy, but it’s rewarding to solve.


Q&A

What do you enjoy doing in your free time?

Before having kids I competed in triathlons.  When I can find the time, I still love getting out on the bike or going for a run (swimming laps is still not my fave).

How do you manage stress?

I picked up the ukulele as my pandemic hobby, and it’s been an incredible stress management tool.  It requires so much focus, that I can’t really think about anything else.

How many cups of coffee do you have in a day?

One.  More than that and I can’t sleep.

Any book or podcast recommendations?

I listen to a lot of podcasts, mostly for fun.  I enjoy Reply All, One Bad Mother, Throughline, and The Memory Palace.

What advice do you have for recent college graduates?

You don’t have to have it all figured out.  Start with something that seems right-ish and keep learning and iterating from there.

About the
Company

Reprise is the product experience platform for product-led growth.

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Lead(H)er Profile - Jess Dashner, Director of Media Strategy & Operations at Gupta Media banner image

Lead(H)er Profile - Jess Dashner, Director of Media Strategy & Operations at Gupta Media

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Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Jess Dashner, Director of Media Strategy & Operations at Gupta Media.


Where did you grow up and how would you describe yourself as a child?

Growing up in Trumbull, Connecticut, I loved learning: learning how other people think and act, learning new things in school, learning about the way the world works and my place in it. If you asked me my favorite school subject as a child, I would have said “all of them.” I wanted to be free to explore all potential subjects, including the ones I was less “naturally inclined” to excel at (I’m looking at you, gym class).

What did you study in college and what was your first job out of school?

Throughout my four years at Boston University, I explored many different potential paths, eventually landing on Psychology, Advertising, and Statistics. After gaining much-needed perspective from internships that spanned agencies, in-house marketing roles, and start-ups, it became clear that I was looking for a role that would combine the versatility of agency life with the challenges of working at a small company that would teach me how to build a successful business, not just work for a successful business. This led me to Gupta Media, which, at the time, was a recently established Cambridge-based digital marketing agency that primarily focused on managing search engine marketing campaigns for record labels. Believe it or not, I’m still there 14 years later, though my role and the agency itself have both evolved immensely since those early days.

Can you share the details on your career path and what were the critical moments that got you to where you are today?

I know that my path has been fairly unique in that I have been with the same company throughout my career. When I started at Gupta Media, I was an individual contributor, responsible for day-to-day campaign management. The first critical moment in my career was one that our agency’s Founder, Gogi Gupta, still remembers fondly every time employee annual reviews roll around. It was the first real performance review of my career, and I went into it expecting the professional equivalent of what I’d come to expect from years of straight A’s in school: put in the work, get the top grade. Needless to say, my review was lackluster at best, and I was left confused and disappointed. It was then that I learned effort isn’t enough in the real world. You need to be able to deliver results and self-promote. Keeping that early lesson in mind, I developed my skills and formed deeper relationships with our clients. This led to more autonomy and bigger opportunities. Early in my career, earlier than most, I was given my own team to manage, along with my own roster of clients. I had just returned from a few months working out of Sony Music’s office in London. I’d just crammed a lot of life experience into a short period of time and was about to embark on a completely different type of professional journey. This was another pivotal “sink or swim” moment for me and one that I’m glad I dove into head first, as it was a very important piece of my journey to where I am today.

What is your current role and responsibilities?

Today, I am the Director of Media Strategy & Operations at Gupta Media, as well as an Account Director within our media department. This position allows me to assume two different roles at once. As Director of Media Strategy & Operations, I help ensure that our immensely talented media department has everything they need to deliver best-in-class work for our clients. This spans a variety of responsibilities, from managing partner relationships, to guiding training and career development, from working across departments to determine agency strategies and POVs, to making sure we’re the first agency to test new opportunities in performance marketing. As Account Director, I oversee our relationship with several of the agency’s top clients while also pitching and onboarding new business.

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position?

I still can’t believe that I’ve been with the same organization since I was 21 years old. To be completely candid, I’ve often wondered if I’m missing out on the more holistic perspective that I could have gained from bouncing from company to company. However, I would have had to sacrifice all of the invaluable experience that comes with growing a successful business over many years of innovating, scaling, and learning. So to answer the question, no this was not where I expected to be in 2022, but it was always my goal to be a valued member of the leadership team at a cutting edge, ever-evolving company.

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?

  • Be hungry, be curious. You can’t move forward in your career unless you’re jumping on every good opportunity that comes your way, and you can’t prove that you deserve those opportunities unless you’re asking the questions and doing the research that it takes to turn those opportunities into success stories.​
  • Start your career at an agency. Agencies allow you to work with a diverse group of clients, industries, and personalities very early in your career. Bonus points if you work at a small agency, where you will also likely work across departments and assume different roles at the same time.
  • Advocate for yourself. As I learned at my first performance review, it’s not enough to work hard and quietly do the job well. You need to make sure your achievements are getting recognized, and you need to stand up for yourself if you’re getting passed over for opportunities that you’ve earned. It’s not always comfortable, but it’s important.
  • Try, fail, learn, repeat. We learn from both our successes and our failures. It’s important to stay nimble and accept that there’s always more to learn.

What are the most important skills that you need to do your job well?

  • Adaptability. Marketing, particularly digital marketing, is an ever-changing industry. If you can’t learn to reprioritize, pivot quickly, and learn without an instruction manual, then you fall behind.
  • Empathy. My job is part client consultant, part team leader. You need to understand where a person is coming from and where they want to go in order to help them on that path.
  • Organization. It might sound like a basic skill, but when you’re part of a team, you can’t afford to be disorganized and unreliable. An organized mind can provide clarity for everyone.
  • Self Awareness. It’s important to lean on your strengths, know how you like to manage and be managed, and be authentic to your own personality. You can fake it ‘til you make it to a certain extent, but at the end of the day, you need to be the best version of yourself to succeed on your own terms.

What do you find most interesting/rewarding about your work?  What’s the most challenging?

Managing people is the highlight of my work. I love being a part of someone’s success story, helping them tackle a challenge by teaching them how to think through a problem rather than dictating  each step to take to solve it. It’s very rewarding to see someone achieve their professional goals, both while they’re at Gupta Media and wherever life has taken them after.

There is never enough time to achieve everything I want to achieve, and sometimes there’s barely enough time to achieve the bare minimum. The same is true for my team, and even for my clients. I’m always wary of burnout, relationships becoming transactional, and sacrificing what is best for what is fastest/easiest.

What is your proudest professional accomplishment?

A few years ago, Harvard Business School selected Gupta Media to be the subject of a case study that examined our unique approach to performance marketing. I worked closely with HBS to discuss our work, as the case delved into the projects that I had personally overseen in my role as Account Director. When the case was ready to be taught to all HBS first-year MBA students, I was invited to lead a Q&A session in one of the classes. It was a true honor to stand in front of some of the brightest minds from around the globe, acting as teacher rather than student.


Q&A

What do you enjoy doing in your free time?

In addition to spending time with my husband and 2-year-old son, I love to walk and run outside, play board games with friends, and eat my way through whatever city I’m in.

How do you manage stress?

A little stress can help get the job done, but a lot of stress isn’t good for anybody. For me, perspective is important. Sometimes, I need to take a step back, look at the situation from a different perspective, and give myself a moment to react without actually acting.

How many cups of coffee do you have in a day?

Current answer: 1-2 cups per week. Plus, I love tea. However, ask me again in a couple of months when I have a newborn and a toddler on my hands.

Any book or podcast recommendations? 

I love the Intelligence Squared U.S. Debates podcast because each episode takes a debate topic and invites highly regarded experts and thought leaders to debate their opposing viewpoints with each other. It’s a great way to learn more about certain subjects, while challenging yourself to approach the debate with a truly open mind that can be changed if the case is compelling enough.

What advice do you have for recent college graduates?

Seize every opportunity you can. Say yes to everything (within reason). If it pushes you out of your comfort zone, even better. Some of the best opportunities are ones you need to ask for, so don’t wait for them to be offered to you. And when you do ask, make it easy to get that “yes.” You might not be ready to take the lead on a juicy new account, but you’re ready to listen in on the pitch or help the team with research. These will all be valuable learning experiences early in your career, so be a sponge.

About the
Company

Gupta Media is a performance marketing agency, founded on the idea that advertising creates huge leverage for our clients.

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Lead(H)er Profile - Anna Fisher, Chief Marketing Officer at Spiff banner image

Lead(H)er Profile - Anna Fisher, Chief Marketing Officer at Spiff

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Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Anna Fisher, Chief Marketing Officer at Spiff


Where did you grow up and how would you describe yourself as a child?

I was born in Russia and grew up in Andover, Massachusetts. I moved to the United States with my family when I was six, and went straight into first grade without knowing any English. That experience definitely shaped me as a child. Instead of regular English classes, I went to ESL. I didn’t like being separated from my classmates and wanted to fit in, so I was really motivated to work hard and figure things out quickly. I think a lot of that drive came from my parents, and just seeing how hard they worked. They also really valued education, so grades were always super important.

Anna Fisher Spiff

What did you study in college and what was your first job out of school?

I majored in communications, with a minor in education. Growing up, I always wanted to be a teacher. I thought marketing was interesting too, but that was originally a backup plan. My first job out of school was in client services at Brown Brothers Harriman.

Can you share the details on your career path and what were the critical moments that got you to where you are today?

I had a great career trajectory at Brown Brothers, but just didn’t feel like I was on the right path. I decided to take a risk and join what was then a small startup, ZoomInfo.

I was quickly entrusted with a lot of different marketing channels. Resources were limited, so I had to prove everything, hold campaigns and channels accountable, and have positive ROI. 

If I made a mistake, I had to fail fast. My team had to be nimble, get things done, and build processes and infrastructure so we could scale. I don’t think I would have really gotten to where I am if I didn’t have that experience.

I stayed at ZoomInfo for eight years, through two acquisitions and an IPO.

What is your current role and responsibilities?

I’m currently CMO at Spiff. My team’s responsibility is two-fold. We're responsible for generating the majority of the pipeline, whether through digital marketing, demand gen, or our SDR org. On the other side, we really focus on the customer experience with new product launches, and making sure our internal team is aware of the incredible solutions we're bringing to market.

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position?

This is definitely not where I thought I’d be 20 years ago, but for the past five years or so, my career has been heading in this direction. I’m really excited for the journey ahead and the position I am in. We have the ability to build a great team and bring an incredible product to market. So grateful for the opportunity I have in front of me.

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?

Be data-driven, and focus on initiatives you can measure and replicate. Then you can double down on what’s working, and stop doing the things that aren’t.

Also, focus on hiring. Find good people who care about and understand the end goal, so you’re aligned. Most importantly, treat them well. I don’t think any person in a senior position could have gotten to where they are or at least been impactful without their team behind them.

What are the most important skills that you need to do your job well?

I think being able to communicate clearly with both the internal team and other stakeholders is crucial— like making sure the sales org understands your goals and strategy. Another important skill is being able to identify the key criteria you should be measuring. Hiring and recruiting is also big, you can find the top talent you need for each individual role on your team.

What do you find most interesting/rewarding about your work?  What’s the most challenging?

Our team sets pretty challenging goals— whether it’s generating new pipeline or launching new productions—  so when we hit them, it’s just super rewarding.

Another thing I really love about my job is being able to promote other people— not just their title and salary, but also the work that they put forth. Focusing on the people is so important. How do we take care of one another? How do we support women on our team? How do we build a core culture of high performers, who are still kind and caring? That’s what I’m really excited to be doing.

As for challenges, we haven’t necessarily had the full headcount we’ve needed to achieve our goals. It takes time to lay the foundations in marketing orgs, and I’m always trying to hire the right people, but sometimes it can feel like refueling in the air.

What is your proudest professional accomplishment?

My team. I’m really grateful to have had so many people follow me when I joined Spiff. Everything we’ve accomplished so far would have taken longer and been harder if we didn’t have such an incredible core team, who put their trust in me before there were any major marketing initiatives here. At the same time, I think new perspectives are so important. I’m just so unbelievably proud of our team and excited to continue growing.


Q&A

What do you enjoy doing in your free time?

I love spending time with my family, and try to get everyone together at least one a month. I also really enjoy trying out new restaurants with my friends and traveling with my husband.

How do you manage stress?

I make lists, identify my biggest priorities, and then try to not to worry about the smaller things at first. Sometimes I have to reshuffle, but it helps keep my focus on what’s most important.

How many cups of coffee do you have in a day?

I try to limit myself to one Venti, and spread it throughout the day.

Any book or podcast recommendations?

I really enjoyed Essentialism by Greg McKeown. I think a lot of women say yes when they shouldn’t, because they have enough on their plate already. I try to focus on the most impactful things on any given day, and this book has some great guidance on how to do that.

What advice do you have for recent college graduates?

Don’t get hung up on what title you think you should have, or the salary you believe you deserve. Just get in there, do the work, and get your hands dirty. If you work hard, you’ll move up quickly. If you can find something you love, things won’t feel as tedious along the way. Also, learn from others. Being new is actually a great opportunity, because there are so many smart people willing to help if you ask.

About the
Company

Spiff is the leading sales compensation platform that automates commission calculations and motivates teams to drive top-line growth.

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Lead(H)er Profile - Caitlin Reiche, Chief Commercial Officer at Zus Health banner image

Lead(H)er Profile - Caitlin Reiche, Chief Commercial Officer at Zus Health

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Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Caitlin Reiche, Chief Commercial Officer at Zus Health


Where did you grow up and how would you describe yourself as a child?

I grew up in Newton, Massachusetts - close to Boston. I loved school but wasn’t particularly athletic, and spent much of my time outside of school with my parents, older brothers, and kids around my neighborhood. 

Caitlin Reiche Zus Health

What did you study in college and what was your first job out of school?

I went to Middlebury College, a small liberal arts school in Vermont. After switching my major three times - from economics to history to poli-sci, I finally settled on Psychology, for no other reason than I realized my psych classes were the ones I was always most excited to attend. In retrospect, I realize that the basic concepts of psychology are probably the most important to understand to navigate all relationships, including those in business contexts. But I didn’t always want to go into business - I thought I would be a clinical psychologist and so followed that “path” out of undergrad, and coordinated clinical research trials in the Psychiatry Department at Massachusetts General Hospital. It was in this role where I was first exposed to the inadequacies of existing HCIT and the opportunity for improved technology to provide efficiencies and superior care. 

Can you share the details on your career path and what were the critical moments that got you to where you are today?

During graduate school at the T.H. Chan School of Public Health, I did a consulting internship at Deloitte and worked on a value-based care project for Harvard Business School and Brigham and Women’s Hospital. I knew that value-based care (as opposed to fee-for-service) was going to change the way we think about and pay for healthcare, but I quickly recognized that very little technology existed to support these new models. 

After a number of conversations with folks in my network, I decided to pursue a role at athenahealth, one of the most innovative and transformative healthcare technology companies during that time. Athena was growing quickly at the time, providing a number of opportunities for someone early in their career, like me. I was able to chart my own course there, holding roles in Product Strategy, Corporate Strategy, Enterprise Business Sales, and Product. I recognized I loved building new teams, launching products, and managing and mentoring people.

I have been lucky enough to continue this work at PatientPop and then as Chief Operating Officer at Buoy Health, where for 3 years I built out the organization from 24 to over 100 people. At Buoy, I also had the opportunity to work with emerging digital health companies as they figured out their go-to-market strategies - and this is when I knew I wanted to help this new era of virtual-first healthcare companies succeed, prompting my move to Zus. 

Tell us about your new role at Zus Health?

At Zus, I oversee our new Commercial Team, which includes building out our marketing and product marketing functions, our business development and sales teams, and our partnerships and developer community. 

As a relatively new company, I also spend a lot of time developing our go-to-market strategy. I love the cross-functional nature of the role, and enjoy having daily conversations with some of the most innovative digital health companies that will truly change the way we receive healthcare over the coming years. 

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position?

I wish I could say I planned it, but of course much of the evolution of my career happened organically. Early on in my career, I didn’t think of myself as a salesperson. However, over time, I realized that external, strategic, customer and partner-facing conversations were the most invigorating parts of all of my roles - that introspection helped me realize that a Chief Commercial Officer or a go-to-market leadership position is the best fit for my interests and skills.

Caitlin Reiche Zus Health

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?

I think a tendency is to say - I want to lead a Commercial organization, and therefore I need to “grow up” in sales. I actually think another way to be successful in this type of role is to experience different opportunities in other parts of an organization. Time spent in product or R&D will give you empathy and understanding of the product development lifecycle, time spent building out teams in any role will give you leadership and management skills, a marketing role will train you in critical top-of-funnel strategies… the list goes on. Become a well-rounded professional and then pick the area where you want to lead. 

What are the most important skills that you need to do your job well?

Organization - this may be underestimated, but being really organized about our go-to-market strategy and the tactics that will lead us to success is really important at a macro level, and day-to-day organization and deep preparation around customer conversations, presentations, and follow up is critical. 

What do you find most interesting/rewarding about your work?  What’s the most challenging?

I love this early stage because success (and really, company survival) necessitates that the whole organization puts their energy into go-to-market. This means I get to work very cross-functionally, bringing product managers and engineers into customer strategy sessions and conversations and spending a lot of time sharing insights across the company, 

What is your proudest professional accomplishment?

The times I was able to help another individual realize their full potential through mentorship or management – these have always been the most satisfying experiences for me. 

Are you involved with any professional organizations outside of the company? Volunteer work?

I’m a member of Chief and also mentor for The Roux Institute, a graduate and entrepreneurship organization here in Portland, Maine. 


Q&A

What do you enjoy doing in your free time?

Time outside of work is spent with my family. I have 3 children under 7 and we love our family adventures here in Maine - boating, skiing, and generally spending time outside.

Caitlin Reiche Zus Health

How do you manage stress?

To-do lists and calendar organization, and trying to find some free time during the day when I can take my dog for a walk or go for a run.

How many cups of coffee do you have in a day?

At least 3… but never after 1pm. 

About the
Company

Zus empowers an entirely new wave of healthcare builders to create technologies and services without the usual blockers.
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