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How to Land a Career in Product Management - Top Boston Product Talent Share Their Tips
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Career Path is a regular series on VentureFizz where we connect with individuals from our BIZZpages, which are the fastest-growing tech companies in the Boston tech scene. We learn a lot about each person's background and what a day in the life is like for them.
We have compiled advice from some of the Product Managers that have been profiled. They share the details on how job seekers can obtain a career in the field of Product Management.
"Seize any opportunity you can to take on product management-like responsibilities at your current company, even if there is no formal product management team structure. Express your interest, and take on small tech projects to get your feet wet in working through an initiative from inception, to design, through build, to launch. And if you don’t have a technical background, don’t let that intimidate you. You’ll get used to taking on something that seems insurmountable to understand, and by the end of it, knowing very well what the inner workings are and how to explain them to others. I still face this from time to time and always tell myself that, as long as I keep asking questions, it’s only a matter of time until I understand and can speak intelligently about it."
"Reach out to people currently working in product. Ask to get coffee. Go to meetups and read as much as you can about the role. If you come from a technical background, that’s awesome, If not, don’t be intimidated or count yourself out of a career that really interests you. Figure out what draws you to product. Once you know, repeat that back to yourself and get good at telling that story to other people. If you come from a place of authenticity and genuine interest, people will respond well to that and want to help you as you jump into a new path."
"My biggest tip to someone considering a career in product management is to embrace their background. There is no traditional product manager; the team is made up of people with a wide variety of experiences (professional and personal). I would also advise people to stay current and curious – inspiration can come from anywhere."
"Discover your personal spike? Are you the connective tissue that breaks down organizational silos? Are you the brilliant empathizer that has an uncanny knack for understanding users? Are you the engineer’s best friends with your perfect articulation of features and needs? There are lots of things a Product Manager has to do. Understand your strengths and play to them. Where you are weak, you get to choose: Either improve them or build a team that mitigates your weaknesses."
"Talk to anyone you can who’s an engineer, product manager or designer. Learn about the variations between companies and which type of role you think will be best for you. I also went to a few meetups and introductory courses which gave me some solid baseline knowledge. There’s a ton of great literature out there about the PM role, product teams and how to work best with engineers which I would recommend reading. I found Cracking the PM Interview helpful in understanding what the interview process might look like. Think about what your best entry point is. For me, it has been beneficial to move internally. While I’m learning the role, I’m able to leverage strong knowledge of our product and customers."
Click here for a list of job openings at Jackpocket, or check out the right side of this page!
Where did you grow up? What did your parents do for work?
Luhansk, Ukraine. Later, I won a Green Card lottery and decided to see what the future held for me in New York.
In Ukraine, my mother was a pediatrician and my father was a mechanical engineer. They recently immigrated to the USA, and they’re in the process of finding their path in this country. I respect them for being independent of me; it’s not an easy task to do in a foreign country at their age.
Where did you go to college? What did you study and what were some of your initial jobs out of school?
When I finished high school, I moved to Kharkov to get a degree in sociology. I always loved big cities, which is why I moved from the small Luhansk to the significantly bigger Kharkov. While I was in college I worked with a marketing company. We conducted marketing research, doing all kinds of surveys and focus groups. Companies made advertisements for their products based on the research. I enjoyed every minute of my work.
When I moved to New York I decided to get a Bachelor of Arts from Hunter College CUNY, with a major in sociology and a minor in statistics, to increase my chances of getting a similar job here. While establishing myself in sociology, a friend of mine suggested quality assurance (QA), since it is an easier field to get into without having a master’s degree.
At that time, I thought it was a crazy idea since I didn’t have a technical background. Since I am very adventurous, I tried it anyway. I am glad I did because I like what I do now.
What has attributed to your success thus far and has helped propel you to the position you have now?
A few things:
The most important—my kids. I wanted them to be proud of their mom. I wanted to show them that with enough perseverance and optimistic attitude, you can do anything.
My friends played an essential role too. They helped me to believe in myself and showed me how to not give up.
I always have been lucky with my team. In all the places I’ve worked, colleagues have helped me to learn something new and grow.
Can you share the high-level responsibilities of your current position as Lead QA Engineer at Jackpocket?
I am responsible for overseeing and making sure the Jackpocket apps and website work as expected, so that customer service has as little work as possible. The fewer issues that get into production, the fewer questions that need answering. And this includes making sure new features are usable and clear to end-users.
A big part of illuminating issues in production is established the right processes and communication between different teams. I like to think about QA as an art of collecting business requirements. During the process of building features, requirements get changed all the time. It is important to make sure to flag disconnect in early stages, and to bring everybody to the same page if something changes.
Also, I know it may not seem this way but QAs are trying to save time for engineers. I am always researching what tools to use and what we can do to provide better coverage.
Any tips for someone considering a career in engineering?
If I can do it with my degree in humanities, you can do it, too, if you like learning.
You will always need to learn something new since technologies are changing so quickly. But that’s what makes this field so interesting and dynamic. Also, if you encounter a problem, chances are that somebody else already has a solution. You are not alone. Just Google it.
Day in the Life
Coffee, tea, or nothing? Coffee in the morning and tea during the rest of the day
What time do you get into the office? 9 - 9:30 am
What are three things that motivate you in your role?
It is always interesting to work on innovative features. I like seeing when a new feature is shaping up from nothing.
Customer feedback is also very motivational. It is very satisfying to see that somebody likes your efforts.
Challenges, when you need to figure something out. I get more energetic when I figure out some difficult tasks.
Every day is different, but can you outline what a typical day looks like for you?
Usually, I start by reading emails and Slack notifications. It sets my priorities for the day. Later, we have a scrum meeting where everyone briefs the team about their work progress and challenges. After that, I get to my daily tasks, which usually involves asking a lot of questions. Everyone usually gets some: designers, product, marketing, not to mention engineers. I really appreciate everybody’s cooperation and patience. I am so lucky that everybody works as a team and contributes to the success of the projects.
What time do you head out of the office?
If there are no urgent issues I leave at 5 - 5:30 pm
Do you log back in at night or do you shut it down completely?
I shut it down with very few exceptions. I appreciate that I can do all my work in the office. The schedule at Jackpocket is flexible enough to accommodate different people's needs.
Any productivity hacks?
Get enough sleep. That is why I believe people should shut down Slack and work email at night or during vacation.
Be proud of your work. You need to be passionate about it. Make it interesting and challenging enough to keep you going, if it is not.
Sometimes you need to take a step back from what you are doing to find the best solution.
Always break big tasks into smaller, more manageable pieces.
What are the 3 apps that you can’t live without?
Jackpocket :) I open it every day. We’re on both iOS andAndroid.
Angry Birds Blast. This game helps me to not be annoyed with New York public transportation and regroup after reading news in the morning.
Splitwise. I do not use it every day, but it makes it so much more convenient to track expenses when you organize trips/events with your friends or relatives.
What do you love about Jackpocket?
We have very friendly and unpretentious people. Management puts a lot of effort into making sure people enjoy working here, and it’s very noticeable. We do a lot of fun activities like happy hours, trips to Six Flags, a field day with Zog Sports, and more. And the office is a reflection of who we are, right down to the “Jackpocket blue” of our phone booths.
What professional accomplishment are you proudest of?
I am usually very proud of releasing features that were difficult to develop. That said, I always think that my biggest accomplishments are in my future.
Who do you admire or call upon for professional advice?
It depends on the professional advice I need. I reach out to different people. My husband is probably my most trusted advisor at the moment.
I have a deep respect for people who are passionate about what they do. They usually know a lot of information and think outside of the box.
Alexander Culafi is Producer & Editor for VentureFizz. He also edits and produces The VentureFizz Podcast. You can follow him on Twitter @culafia.
About the Company
Jackpocket is the first mobile lottery app in the U.S. that offers players a secure way to order official state lottery tickets, such as Powerball, Mega Millions, and more, via their smartphones.
Interested in working at BlueConic? Check out all of the company’s job openings on the list to the right.
Where did you grow up? What did your parents do for work?
Igrew up south of Boston in Scituate, Massachusetts. My father spent the majority of his career in tech and about 15 years as the CEO of a few software organizations. My mother started and ran a pre-school in Scituate for about 20 years.
Where did you go to college? What did you study and what were some of your initial jobs out of school?
UMass Amherst. I studied managerial economics and finance. My first job out of UMass was as a Fund Accountant at State Street. They acquired Investors Bank & Trust in 2007 and I worked on the conversion team moving them over to State Street accounting systems. Looking back at those days there were a lot of long hours, problem-solving and implementing new processes. I kid around about it today, but other than the 40,000 employees. It was a lot like working at a growth stage software company!
What has attributed to your success thus far and has helped propel you to the position you have now?
There are a number of things at different points in time; however, the one constant has been the people that I’ve been fortunate enough to work with. They challenge me to be better every day, but you can learn a lot from your colleagues if you pay close attention and have an open mind.
Can you share the high-level responsibilities of your current position as VP, Inside Sales at BlueConic?
Helping marketers realize that individualized marketing is a reality and helping them put plans in place to help them achieve a unified and actionable single view of their customer.
Coaching, hiring, and retaining exceptional members of our Business Development, Sales, and Sales Engineering teams.
Collaborating across departments to create and implement strategies for both inbound and outbound pipeline generation.
Analyze historical data and trends to build models for scaling our sales organization as efficiently as possible.
Any tips for someone considering a career in Sales?
Be incredibly curious and always focus on how you can improve. Regardless of how great the training program is at your current company, always look outside of your company to learn as well. I’d say the same to someone who has been in sales for 10+ years. New ideas and new approaches create good habits and prevent laziness or bad habits from forming.
Jim Collins speaks about “the window and the mirror” in his book Good to Great. The concept is perfect for people starting out in sales. If things are going well, look through the window and give everyone around you credit. If things aren’t going well, look in the mirror, take ownership of finding how to fix things. Far too often sales reps do the exact opposite.
Day in the Life
Coffee, tea, or nothing?
Coffee, one in the morning and another around 2:30 PM every day.
What time do you get into the office?
Usually between 7:30 and 8 AM.
What are three things that motivate you in your role?
The people I work with. Their passion and work ethic are absolutely relentless.
Knowing that we’re doing something different. No one has built this company, in this category, with these people. There are new challenges and new achievements every single day.
The opportunity to help define the Customer Data Platform (CDP) category and helping change the way marketers think about individualized marketing.
Every day is different, but can you outline what a typical day looks like for you?
Before Work: I like to work out in the morning before commuting. During the commute, I run through my calendar to make sure I’m prepped for the day and then will run through the pipeline to make sure we have plans in place each day to move things forward.
Morning: Before 9 AM, I’m doing deeper analysis and tasks that require more focus. I try to most of my coaching in the morning so we can focus on statistics and I can focus on my team before too many distractions come up.
Lunch: I’m a creature of habit, most of my lunches are spent working at my desk and 9 times out of 10 it’s a salad from UDG or sweetgreen.
Afternoon: I’m almost always on sales calls with my team or collaborating with other departments in internal initiatives.
After Work: While commuting home I’m making sure any materials or information that I’ll need for the following day are prepped and ready or I’m making sure all of my action items for the day are taken care of.
What time do you head out of the office?
It really depends on what is in my calendar but usually between 5:30-6:30 PM.
Do you log back in at night or do you shut it down completely?
I try really hard not to log back in every night, but sometimes it can’t be avoided. I probably log back on 50% of the time. I’m always available if one of my colleagues needs me via Slack or email.
Any productivity hacks?
Figure out what the best way is to organize your to-do list and commit to it. Some use tools like Trello and some use a notebook. Figure out what works for you. I’ve tried a number of apps, but always come back to my pen and pad.
Try to organize your day by when you focus best. I tend to be more analytical in the mornings and more creative in the afternoons. In knowing that I try my best to organize my tasks to optimize my day.
Music! Create a playlist that you listen to when you need to really concentrate and only listen to it while you’re focusing.
What professional accomplishment are you proudest of?
Watching people that I’ve coached and trained get promoted and excel in their new role is incredibly rewarding. I think my most proud accomplishment is still being developed. We’re writing an amazing story here at BlueConic. That story won’t be my individual accomplishment, but I’m extremely proud to be an element of what we’re building.
Who do you admire or call upon for professional advice?
There’s a long list of people that I have admiration for and who have helped me in various situations. A number of my good friends hold similar roles at relatable companies and often act as a sounding board. My father loves to share stories from his career and tie them back to what I’m working on. Lastly, my colleagues and team members at BlueConic have been an incredible resource.
The world’s leading customer data platform, liberates companies’ first-party data by giving business users access to unified and actionable customer data that offers both confidence and utility whenever and wherever they need it.
Where did you go to college? What did you study and what were some of your initial jobs out of school?
Boston College, Carroll School of Management with a Marketing concentration. My initial job out of undergrad was at a consumer marketing agency in Boston. I was fortunate to align myself with one of the SVPs who was starting a healthcare practice within the agency. Both my parents and my older brother are clinicians, so there was this innate interest in joining this emerging healthcare marketing group. I quickly got plugged into client assignments across health systems, pharma, payer, policy work, and medical devices. I’d say that diversity of work was the catalyst for my desire to learn more about how these disparate areas all worked together to deliver positive patient experiences.
What has attributed to your success thus far and has helped propel you to the position you have now?
In the first few years of my career, I had the opportunity to work for incredibly smart, committed, and hands-on leaders. I was young and impressionable, and they were willing to help me learn, bring me into many c-suite and senior executive meetings and strategic planning initiatives. It forced me to mature professionally very quickly, exposed me to higher-level thinking, and definitely shaped how I approach business. It also had a lasting impression on my management style.
Can you share the high-level responsibilities of your current position as Director of National Hospital Growth at PatientPing?
At its most basic level, I am responsible for building and managing the team that sells PatientPing’s solution to hospitals and health systems across the country. We have growth goals to hit and I need to make sure the team is organized, aligned, and ready to achieve the goals. More broadly, I have the responsibility of helping inform our cross-functional teams about market trends, customer needs, product opportunities, where we should prioritize/invest, and more.
Any tips for someone considering a career in sales for a high-growth organization?
Step outside the concept of a comfort zone - you can’t have one if you want to be successful in sales for a high-growth organization. Ask questions and be studious. Absorb as much as you can. Be flexible, courteous, respectful, and live up to your word. Every customer is different, every opportunity is different, and it’s your job to assess those dynamics quickly, pivot where needed, take punches, and solve problems. Always take full accountability. On our Growth team, everyone has a specific job to do. If you can’t get it done, no one is there to do it for you. Lastly, find your own motivations and stay true to them. Success is binary - you either got it done or you didn’t - so you need to find wins and celebrate them along the way, it’s the only way to keep energy and optimism while moving forward.
Day in the Life
Coffee, tea, or nothing?
Coffee, splash of milk. I generally stick to 1 cup a day.
What are three things that motivate you in your role?
Building the team that’s going to win deals and build our customer network.
Helping the team win deals and build our customer network.
Feeling the incremental progress each day that is contributing a much bigger mission.
Every day is different, but can you outline what a typical day looks like for you?
I have 3 little boys, so everyday starts by 6 AM with someone jumping on me in bed.
Once I’m awake, I’m on email and slack. I’m not really proud of that, it’s a bad habit. I prob do 10-15 min of work before getting out of bed.
When I can, I try to sneak in a few miles on the treadmill.
I live south of Boston, so I take the Commuter Boat up from Hingham. It’s some of the most productive time of my day.
Once in the office, it’s a race, my calendar is filled with meetings that support the growth of our team and business. I consider my commute time my “blocked” time where I get an hour at the beginning of the day and an hour later in the day to catch up on any open items.
I try to sneak out of the office early so I can get home for dinner with my wife and kids. This is one of the only non-negotiables for me. I’m going to get home to spend some time with my family and, at the very least, be a part of dinner and bedtime.
Read books to kids and get them in bed
Hang with my wife - catch up - might be over a show, a drink, or a sports game on TV.
Emails and unfinished work before calling it a day.
Any productivity hacks?
There are no hacks to hard work.
What are the two apps that you can’t live without?
LinkedIn
Spotify
What professional accomplishment are you proudest of?
I’m most proud of what we’re building at PatientPing. This is no small feat - engaging and connecting the largest and most respected health systems and the community of providers who help them care for shared patients. What we are doing is transforming healthcare and I’m so proud of that endeavor.
Bamboo Health is an innovative healthcare technology company and the leaders in real-time care intelligence. Empowering the Right Decisions, at the Right Time, for the Right Outcomes.
Where did you grow up? What did your parents do for work?
I grew up in North Kingstown, RI. My father was a middle school history teacher and later a high school guidance counselor. My mother was a middle school home economics teacher and later a high school art teacher.
Where did you go to college? What did you study and what were some of your initial jobs out of school?
I majored in Art, Philosophy & Literature with a minor in Systems Engineering at the United States Military Academy at West Point. I later studied Film Directing and Production in UCLA’s Graduate Film Program. My first jobs after West Point were as a rifle platoon leader and mortar platoon leader with the 101st Airborne Division in Iraq during Operation Iraqi Freedom I. While I was in grad school I did everything from assistant editing gigs for reality television shows to teaching film to working as a bouncer at night clubs and hotels.
What has attributed to your success thus far and has helped propel you to the position you have now?
The leadership training I received at West Point, in Ranger School and through leading platoons in combat was second to none and greatly contributed to my success so far.
Can you share the high-level responsibilities of your current position as Vice President of Enterprise Sales at Quick Base?
Collaborate with customer base to align our platform with their business needs
Identify and share new ways that our customer base can leverage our platform
Build, drive and report on my team’s pipeline
Partner cross functionally with sales enablement, customer success, product, marketing, legal, finance, and ops to continue to drive efficiency in our sales team and sales process
Hire, coach, mentor and retain exceptional sales talent
Any tips for someone considering a career in Sales?
I think there will always be a place in Sales for highly curious, technically savvy people with strong oral and written communication skills.
Day in the Life
Coffee, tea, or nothing?
Coffee
What time do you get into the office?
Between 7:30 and 8:30 most mornings.
What are three things that motivate you in your role?
Helping people grow professionally
Collaborating with customers that are energized by our platform
Working in a market that is largely undefined with a platform that is the leader in that emerging space.
Every day is different, but can you outline what a typical day looks like for you?
Supporting account executives and managers on customer calls or face to face engagements
Working with account executives and managers to build effective account plans
Inspecting and building a rolling 90-day forecast/pipeline
1:1s with managers and account executives
Interviewing or phone screen prospective candidates for our team
What time do you head out of the office?
Between 5 and 6:30 most nights.
Do you log back in at night or do you shut it down completely?
I log back in at night.
Any productivity hacks?
Meditation. Sometimes you only need 10 minutes of silence to look at a problem in a different way.
What are the 3 apps that you can’t live without?
Quick Base
Spotify
Audm
What professional accomplishment are you proudest of?
Seeing members of my team get promoted to run teams of their own here at QB.
Who do you admire?
I admire all members of my veteran extended family, but particularly those that are working day in and day out to overcome physical and/or psychological challenges that they developed overseas as a part of their service to our country.
Where did you grow up? What did your parents do for work?
I was born in West Roxbury, MA and grew up in a small town in Western Massachusetts. My parents are consultants in the engineering and software industries.
Where did you go to college? What did you study and what were some of your initial jobs out of school?
I went to Saint Anselm College, where I studied Economics and Public Policy. Upon graduation, I wanted to take the time to explore different opportunities. I worked at the Department of Commerce, a small marketing firm, and coached lacrosse. Through coaching, I expanded my network and had the opportunity to meet with sales leadership at SmartBear. I left the meeting excited and inspired by this growing company and knew I had to get involved.
What has attributed to your success thus far and has helped propel you to the position you have now?
They say curiosity kills the cat, but I would argue otherwise. If I had to boil my success down to one word it would be curiosity. This attribute has led me to challenge the status quo, continuously learn, and take risks.
I’ve been fortunate enough to have grown significantly in the year I’ve been at SmartBear and I attribute that success to the environment here. I am surrounded by intelligent, driven people. Coworkers in any department are always available to discuss ideas or questions I might have. Starting in business development taught me about the challenges our customers face, and how we can help improve their everyday lives. My manager gave me a great foundation in software sales which I was then able to build upon.
Due to the growth of our organization, I was asked to become a team lead, managing 10 other team members on the US Sales Development Team. And more recently, I have been promoted to Account Manager. Though each role has been demanding, I work with a great team that ensures success.
Can you share the high-level responsibilities of your current position as Account Manager at Smartbear?
I work with customers in highly regulated industries, such as aerospace and defense, banking, and aviation, to improve their software development process. This requires finding and connecting with the proper stakeholders to understand the issues they face and develop a possible solution.
Any tips for someone considering a career in your field?
This is a high paced environment. Be constantly curious and try to learn as much as you possibly can. Once you think you've learned enough, be prepared to adapt quickly. What works today, might not work tomorrow.
Day in the Life
Coffee, tea, or nothing?
Coffee. Probably too much coffee.
What time do you get into the office?
8:15 AM
What are three things that motivate you in your role?
I’m motivated by the will to succeed, the desire to continue to learn, and seeing those I mentor succeed.
Every day is different, but can you outline what a typical day looks like for you?
Before I leave work, I make a list of everything I want to accomplish the next day. When I arrive in the morning, I prioritize that list based upon any new emails or notifications I may have received and I hit the ground running!
What time do you head out of the office?
5:30
Do you log back in at night or do you shut it down completely?
Will this be published? Then I am always available.
Any productivity hacks?
Butter in said coffee.
What are the 3 apps that you can’t live without?
News, Lyft, and Calculator
What professional accomplishment are you proudest of?
I most proud of my growth at SmartBear over the past year. I have been trusted with the responsibility of leading a team, and then earned the opportunity to contribute to one of the most profitable products.
Who do you admire or call upon for professional advice?
Both of my managers have been great resources. Each started where I was, and have established themselves as trusted voices at the company. I have yet to encounter a situation where I couldn't go to them and have an honest dialogue.
Where did you grow up? What did your parents do for work?
I grew up in a suburb of Milwaukee. My parents were professors of Biology and Political Science. They were big proponents of learning math.
Where did you go to college? What did you study and what were some of your initial jobs out of school?
I went to Yale University for undergrad, where I majored in history. I also took a substantial number of CS courses, but Yale doesn’t give minors. My first job was in consulting as an analyst. I quickly switched from being the analyst to writing code.
After that, I went to a startup followed by some government work when I was in D.C. I also got an MBA from the University of Maryland, where I concentrated in IT and finance.
What has attributed to your success thus far and has helped propel you to the position you have now?
I love solving problems and building solutions. From working in a lot of industries and roles – analyst, UI engineer, full stack engineer, QA engineer, data engineer, system architect – I can approach a lot of problems from all these perspectives and ensure my team is building something that is maintainable, testable, and reliable.
Can you share the high-level responsibilities of your current position as Software Manager at Chewy?
I put the building blocks for what we need to build in the proper execution order, keeping in mind technical dependencies and time to execute. I ensure “planned work” is broken down to levels that engineers can actually execute. I keep engineers in check to deliver projects by our committed dates. I work with the engineers reporting to me to grow their technical and business skills and advance their careers.
Any tips for someone considering a career in Software Management?
Work on different types of systems, in different languages, in different roles. There is something to learn in each of them and make it easier to understand why various elements are important.
Your role is to remove other people’s problems: conflicts with other people, problems with tools, and so forth.
Day in the Life
Coffee, tea, or nothing?
Mostly tea. Some soda, but I keep working on cutting down.
What time do you get into the office?
I’m in “early” just after 8 a.m.
What are three things that motivate you in your role?
Building a system that makes users’ happier.
Having a clear, actionable road map that I can dig into.
Work camaraderie.
Every day is different, but can you outline what a typical day looks like for you?
My day starts before I’m in the office. I’m checking emails by 6 AM and leave the house at 7 AM to catch the train. Then I’ll spend my commute getting my calendar and to-do list in order and sending emails as needed.
In the office, I spend time meeting with users or product managers on clarifying requirements and priorities. Then I’ll meet with engineers about technical decisions and project break down. I usually run scrum. I’ll have a couple “scrum of scrum” type meetings where we go over cross-team technical dependencies. If it’s my one-on-one day, I’ll spend a lot of time talking to my engineers about how they are progressing in their goals and any issues they have.
The remainder of the time is spent fixing any issues that come up, so the engineers can code unhindered, or a project can be unblocked. A lot of this is Jira management: creating, updating, documenting tickets. I’m rarely writing code or executing proofs-of-concept, but I will direct others in how to do these. Other times it’s writing up documentation or presentations of the work being proposed or being completed. It all depends where in the lifecycle various projects are.
When I leave the office, I have my off-line time until later, when I’ll finish up a couple tasks that I can do out of the office.
What time do you head out of the office?
Most days I leave about 4:30 PM.
Do you log back in at night or do you shut it down completely?
I usually work 1-2 hours at night. The paperwork doesn’t usually get done while I’m in the office, so I spend the evening filing tickets of various sorts and reviewing others’ work.
Any productivity hacks?
Block time on your calendar for any task you need to do that will take more than five minutes. And delete or file all email that isn’t immediately needed. I almost never get to “inbox zero” but I’m happiest under “inbox 10”.
What are the 3 apps that you can’t live without?
Fantastical. It has all my calendars (10!) combined and the natural language for entering new events is really useful.
Evernote. My notes go everywhere on every device, so it’s easy to review even without my computer.
Spotify
What professional accomplishment are you proudest of?
I mentored an off-shore (not contractor) team at a large multi-national corporation that had few coding skills at the outset, to executing a total rewrite of the BI reporting system. We integrated six completely different ERP systems from four countries into a cohesive interface that did not have 10,000 fields and everyone defining a different “truth”. It was the old way of doing things.
The end result was a fast, responsive, clear system everyone loved. It was hard work, as many on the business side had their reasons why field #5003 needed to be included, and why field #23 which was virtually identical could not be used. But, I eventually got them all to agree on the critical few requirements.
Along the way, the development team learned several programming languages, how to use source control, how to do code reviews, how to deploy code, and even some aspects of writing unit and integration tests. Who do you admire or call upon for professional advice?
I check in with some grad school colleagues from time to time.
Where did you grow up? What did your parents do for work?
I grew up in the small town of Pepperell, Massachusetts. My mother is a systems analyst, and my father is a driver for a natural gas company.
Where did you go to college? What did you study and what were some of your initial jobs out of school?
I went to the University of Massachusetts Lowell. I studied information technology with a focus in computer science-related courses. I also received a minor in business during my time there. Initially, during and right after college, I was doing freelance Web Development for small businesses and shortly after that, I began working at HealthcareSource as a Web Developer.
What has attributed to your success thus far and has helped propel you to the position you have now?
I attribute most of my success to passion and flexibility. I have always wanted to develop software dating back to my early high school days, and I still love doing it today. For flexibility, I learned that when a challenge is presented, regardless of how hard the task may be, embracing it and completing it with a positive attitude will open more opportunities in the future. There will always be those assignments that nobody wants to do, but it’s essential to your managers, employees and beyond. In the end, it helps to drive others around you to do the same and has helped me become a better leader.
Can you share the high-level responsibilities of your current position as Lead Software Engineer at HealthcareSource?
My current position is half development and half management. I am fortunate to lead and architect/design multiple projects in parallel and contribute to the developing of those projects. In addition, I am involved with mentoring others on those projects and provide direction to help get their tasks completed.
Any tips for someone considering a career in Software Engineering?
Software engineering is full of opportunities. I believe anyone that has the passion for building software can do it with the correct training. You should never say to yourself "I am not a X type of person, so I don't think I could do it". There is no perfect "type" of attitude, personality, etc. to become a software engineer. If you can be passionate about becoming a software engineer, then one day you will!
Day in the Life
Coffee, tea, or nothing?
Both
What time do you get into the office?
I usually arrive between 7:30 and 9 AM. The time varies based on the day and my meeting schedule.
What are three things that motivate you in your role?
The first thing is the challenges that arise every day. In a typical day to day, something "unexpected" will happen large or small. This is not a negative thing, and it is just a challenge that I get to accept and work with my teams to solve.
The second thing is seeing growth. It is always exciting when you complete a tough task. It is even more exciting to help a direct report complete a task and see them get excited.
Lastly and most importantly client exposure. This can come in the form of face-to-face or simply word of mouth. Building software is a challenge, but in the end, there is no better feeling than seeing clients get excited to use things that I have built.
Every day is different, but can you outline what a typical day looks like for you?
A typical day to day starts with syncing up with my teams and the projects that we are working on. Afterward, I get the chance to help anyone directly who has questions or needs a hand with something. After that, I catch up on any code reviewing that needs to be completed. Once that is done, I work on my own development tasks. Staggered a crossed this typical day to day would be responding to emails, chat messages, and attending meetings. This, of course, is very flexible, and the order may vary based on meeting schedules.
What time do you head out of the office?
Typically, between 3:30 and 4:30 PM. This time also varies based on the day and my meeting schedule.
Do you log back in at night or do you shut it down completely?
I typically log in most nights of the week or at least have push notifications on my phone for my work emails and chats. This is however by choice as I have never been asked to work extra hours. I consider developing software also to be a hobby, not just a career.
Any productivity hacks?
Compiling some software solutions can take 30 seconds to 1 minute. Having two monitors is key. How long does it take you to read a typical email or respond to a quick chat? I bet there are some that take less than one minute. Multi-tasking can go a long way if it can be done without losing focus on your primary task. Also, as any Software Engineer will tell you, know and use your keyboard shortcuts!
What are the 3 apps that you can’t live without?
Amazon - As dangerous as "Buy with 1 click" might seem, it saves you a lot of time!
Marriott - I use this all the time to book hotels for traveling. The point system is great.
Uber - There is nothing better than staying inside warm until you can see your driver pulling up from the map!
What professional accomplishment are you proudest of?
I am most proud of my ability to grow professionally in a company. Over the last seven years it was not always easy, but it was always exciting. Going from doing small, simple tasks to architecting brand new software and enhancements to existing software is a huge step towards where I wanted to be. The tasks I was completing went from small client specific enhancements to large client specific enhancements. After that, I was working on small application enhancements which progressed towards larger enterprise-level enhancements. This eventually grew into building new large, enterprise level applications from the ground up, making architecture and design decisions while doing so. I have certainly had many different job titles, but the more important thing is I took the opportunities to grow professionally as they came which is something that is ultimately important not just to my company but to me personally as well.
Who do you admire or call upon for professional advice?
My mother has always been a great mentor to me. She understands the environment I work in and has also been through similar career advancements in the tech industry. Her encouragement has played a critical role in where I am today!
Where did you grow up? What did your parents do for work? What was your very first job (before any internships)?
I grew up in Cincinnati, Ohio. My dad owned his own landscaping company, and my mom was a teacher. My very first job was starting my own lawn mowing business.
You graduated from Boston University in 2008, right as the financial crisis was about to hit. What were your initial jobs out of school and what did that period teach you?
My initial job out of school was to lead the writing program for an ESL tutoring organization. I was laid off after a year-and-a-half there. Following that, I was unemployed for the better part of a year. No period of time post-college has taught me more. It’s what I think of the most as I interact with job-seekers. I’ll never forget how brutal it was to search for a job during that time with minimal work experience that was relevant to the areas I wanted to take my career.
How did you get into recruiting?
I fell into it. I was called by a recruiting firm that was willing to train me, and I didn’t have many other options. I realized very quickly how much I loved it. It allowed me to help people every day, and eventually teach and train new employees on what I had learned. Those were two things I was interested in doing before starting my career in recruitment, so it was a natural fit.
What did you learn in terms of running recruitment process outsourcing programs at large companies like CVS Health, General Motors and other companies?
I learned that even the largest and most successful companies in a given industry undergo large-scale, tumultuous change with surprising frequency. Companies are merging, getting acquired, and buying out other companies like never before. It helps me greatly to structure conversations with people that get caught up in those situations and are affected personally by them.
Why did you decide to join the recruiting team at athenahealth and can you share the high-level responsibilities of your current position as Technical Recruiter?
First and foremost, I wanted to join a software company that builds products that genuinely help people. Athenahealth is the epitome of that. Secondly, I wanted to find a team that I liked as much as my team at my last company, which set a high bar. I’ve never felt more aligned with an interviewing team as I did following my interviews with athenahealth.
As a Technical Recruiter, I support some of the most niche areas of the business, including Infrastructure-as-a-Service, Platform Engineering, and Business Intelligence. IaaS and Platform are working towards enabling microservice architecture via automated solutions across the entire technology stack. Business Intelligence is working towards providing reporting services across all areas of the business. Needless to say, it’s an exciting time to join any of these three groups!
I spend most of my time fleshing out a sourcing strategy for finding the best talent in these areas. I’m always exploring new ways to source, organize and present information, and collaborate with technical teams to build an airtight end-to-end hiring process.
Day in the Life
Coffee, tea, or nothing?
Coffee
What time do you get into the office?
Usually 8:30 AM.
What is something you look forward to everyday in your role?
Using tools that are new to me, and discovering ways of using them to make my life and my managers’ lives easier.
Every day is different, but can you outline what a typical day looks like for you?
I’ll always spend a chunk of time in the morning organizing my day. I’ll usually source and reach out to candidates in the morning, and schedule phone screens for the afternoon. These activities are spread around meetings I have with my internal team, and also with my hiring leaders. I do also spend time every day learning more about the roles i’m staffing for and the techniques I can utilize to best fill those roles. This involves watching online classes in Cloud Engineering and other subjects, watching product demos, etc.
What time do you head out of the office?
Usually about 5:30 PM.
Do you log back in at night or do you shut it down completely?
I log back on. Often candidates cannot talk during working hours, so I need to make sure I make myself available to them as needed.
Any productivity hacks?
Yes - the system that I use to track all progress on a given position is the same tool I use to correspond/collaborate with the hiring teams that I work with. It’s saved me a lot of time.
What are the 3 apps that you can’t live without?
Mint, Spotify, and Reddit
What professional accomplishment are you proudest of?
My best stretch of hiring when I was supporting Equifax for Sevenstep. I went over 13 months without a single offer decline, which included a month with 18 hires (3 of which were SVP level, 1 of those 3 had been open for over two years before I filled it).
Who do you admire or call upon for professional advice?
My best friend Tom. He began his career for a marketing agency, and he’s made his way into a DevOps engineering role without a degree in Computer Science or any formal training on the subject. He’s a great example of how much someone can do professionally when they dedicate themselves to moving into areas that might be out of their comfort zone.
Where did you grow up? What did your parents do for work?
I grew up in a town called Harvard, Illinois near the Wisconsin border. My mom was a teacher of all different types (she also has a law degree). Although we lived pretty far into the country, my dad worked as an attorney in downtown Chicago. As a kid, I spent a lot of time roaming around the woods surrounding our property and both reading and emulating Calvin and Hobbes comics. Pretty much the rest of my time was spent playing piano.
Where did you go to college? What did you study and what were some of your initial jobs out of school?
I attended Illinois Wesleyan University (IWU) in Bloomington, Illinois after a tough decision against pursuing piano performance. Instead, I enrolled at IWU as a biology major. By sophomore year, I switched to a religion major while I worked at the campus newspaper and the campus radio station. By junior year, I added an English and writing double major, and going into senior year, I was editor-in-chief of the campus newspaper. I still credit my time behind the wheel of The Argus as one of the most eye-opening and best educational experiences of my college and early career.
After school, I had a brief stint at the University of Chicago in a religion graduate program, from which I ended up withdrawing. At the same time, I was working the phones in an hourly job for TMC, a division of C.H. Robinson (a F250 transportation and 3PL company). I also did contract work in search engine optimization and content development for a company called L2T Media.
Garrett and his wife, Linda Martin, in London
What has attributed to your success thus far and has helped propel you to the position you have now?
For better or worse, if I’d continued in the graduate program I was in, I wouldn’t be here now. That’s not to say I regret it at all though: I got some real exposure to handling debt, grappling with sunk costs (and their associated fallacies), and weighing my pride and the idea of quitting against the likely outcomes and my personal happiness. I made the right choice, and I believe that you can learn a lot from agonizing over hard choices.
There may be a way in which that decision caused me to double down at the job I was working. I really dedicated myself to my career, and over the next several years at TMC in Chicago, I worked my way through several promotions into a key role in their internal Operational Excellence group. This role stoked my interest in consulting as a general career path and in technology (especially automation) as a focus.
What made the most difference at that early stage of my career was an obsession with efficiency, including typing speed, automation, templates, and organization, which freed up time to self-teach. There was no problem that I wouldn’t try to figure out myself first before I asked someone else. If you can afford to spend some time digging around and trying things yourself, you can learn all you need. If you don’t have time to do that, you have to make time for it first.
Can you share the high-level responsibilities of your current position as Senior Solutions Architect at Bullhorn?
Solutions Architect is a broad term, which can mean varying degrees of pre-sale business engagement and technical delivery engagement depending on the business. At Bullhorn, the role truly encompasses both, but a descriptor that really resonates with me is “Solution Owner.”
If we’re implementing our software for a client, we have a project manager who is the delivery owner, but we, as Solution Architects, are responsible for helping to ensure that the holistic solution works for the client. This goes beyond ensuring that our software does what it’s intended to do as outlined in the statement of work. We also need to know what systems the client depends on for their day-to-day operations beyond our software and how our data needs to interact with theirs.
Any tips for someone considering a career in Client Services?
A genuine interest in positive interactions with other people, even those you know little or nothing about, is the single most important piece. Dedication to your customer’s success is table stakes; to excel, you have to put yourself and the urge to blame aside, and refocus on the problem you have in front of you.
If you can find a way to build a rapport with your clients, you’ll enjoy making them successful. Face-to-face interactions make this easier, so I’d recommend opportunities to connect in-person with your clients. Bullhorn hosts an annual conference series called Engage that creates an opportunity for everyone in our company to meet our customers, and it’s consistently a highlight for me.
Beyond this, building your personal toolset is a key ongoing project. Whatever your specialty, try to broaden your horizons. For me in the technology and software space, this means looking at methods of conflict resolution and negotiation (I love the book “Getting to Yes”by Roger Fisher and William Ury), trying to understand profit and loss and balance sheets, and brushing up on consulting skills. Some classic consulting case interview preparation and practice is invaluable for anyone who aims to grow their career.
Garrett Rapp in San Francisco
Day in the Life
Coffee, tea, or nothing?
Lots of coffee! Not too picky about it - I’ll trade quantity for quality here.
What time do you get into the office?
About 7 a.m. I get a lot of mileage out of the first 1.5 hours of office time before my email, phone, and Slack messages start increasing. If I’m onsite with a client, the goal is arriving a minimum of 15 minutes before any meetings with them start, but ideally 20-25 minutes so I’m ready for a productive conversation.
What are three things that motivate you in your role?
I care deeply about my team and my department. I’ll go a long way to help other people in my organization because I like seeing them succeed.
Getting to be a problem-solver. In most jobs, when you get handed a problem, you actually have a plethora of resources, tools, and some time allocated to solving it. Real-life problems aren’t always that accommodating!
Getting to meet, understand, and make a difference for customers directly. I love working with end users of our software (especially in-person, like during user acceptance testing cycles) and helping them learn new things about the tool.
Every day is different, but can you outline what a typical day looks like for you?
This varies throughout the year based on what project I’m working on, but it can involve:
Participating in client calls (design and requirements, demos, handoffs, and defect reviews)
Participating in internal calls with our sales department
Creating statements of work for services engagements
Creating functional specifications for custom apps and automations
Troubleshooting or testing our software and custom automations
Deploying our software
What time do you head out of the office?
Anywhere from 4 p.m. to 6 p.m., depending on what’s going on that day. All bets are off when I’m on-site with a client though - spending from 7 a.m. to 10 p.m. with a client in their “War Room” builds camaraderie!
Do you log back in at night or do you shut it down completely?
I often will log back in at night, if only to file away emails that I don’t have to respond to, or hit off quick answers. I don’t find it stressful to keep up on things after hours - it’s worth it to me to have less noise waiting when I kick off in the morning. It’s relatively rare that I need to get on the phone with my project teams or clients for urgent matters. That said, as a project and implementation consultant, there will be occasional evenings or weekends for working on big deployments and go-lives.
Any productivity hacks?
I couldn’t live without organized folders in my inbox, my desktop, my Google Drive, etc.
Know when to block yourself off and “hide.” If I have a deep, detailed technical specification to write, I’ll minimize email and Slack, silence my phone, and work in an obscure conference room to avoid interruptions.
I think it’s pretty common to freeze up or procrastinate when faced with tough problems. The key thing is to start on them anyway: start simple and don’t aim for perfection, but just start producing something. You can always improve it later, but you haven’t wasted time avoiding your main problem or displacing it with lower priority issues and requests.
What are the 3 apps that you can’t live without?
Slack isn’t “the email killer.” Email has a very clear purpose and utility, but I do think that Slack is the ultimate office chat tool, and its iPhone app is excellent.
For traveling, ExpenseIt lets me photograph receipts and automatically puts their costs, comments, and allocations into my open expense reports. It’s a great way to not lose track of the money I spend while traveling for business.
I use the basic call, calendar, and mail apps a lot, but the other key apps in rotation would be podcasts and Spotify, especially for when I’m traveling.
What professional accomplishment are you proudest of?
Working my way into a technical and software specialist role over the years, given my lack of a technical and software degree, is my proudest accomplishment. The challenge now is staying up to speed!
Who do you admire or call upon for professional advice?
If I call someone for professional advice, it’s likely to be a parent or sibling (who are all pretty accomplished). In terms of admiration, it would be one of my first managers - Adam Gerdel. He ran the Operational Excellence team at my first job, and he became a big role model for how to develop teams that want to work together, how to deliver results while also making time to think outside of the box, and how to support employees both personally and professionally - all while staying ruthlessly focused on efficiency and innovation. He’s a one-in-a-million team leader, and I’m grateful for all that I learned from him.
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