Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Hillary Wyon, VP of Product at EF Education First.
Where did you grow up and how would you describe yourself as a child?
I was born and spent my early childhood in Wolf Point, a small town in northeastern Montana on the Fort Peck Indian Reservation. When I was 10, my family moved to Brookline, MA as a result of economic challenges in Montana at the time related to drought and oil prices, and to be closer to my grandfather. It was a major culture shock. Montana definitely defines my sense of home but moving also afforded me so many opportunities I would never have had. I have also never been afraid to move around. In many ways, this experience of moving across country and to a new life reflects the kinds of experiences we seek to convey to our customers in my job. Helping people step outside of their comfort zones, see and experience something new, or learn something new about the world and their place in it. As a child, I was a dreamer and a dedicated reader, an extroverted introvert. Largely how I would describe myself still.
What did you study in college and what was your first job out of school?
I focused on psychology and creative writing in school, after a pre-med stint. I took a circuitous path through college and worked full time while going to school at night. I was an assistant teacher for Beginners Spanish for high school freshmen. I was the Assistant Head of Facilities at an independent school in the Boston area, involved with event management, building and security management, and maintenance and new construction builds. I worked at a children’s book publisher in operations. All that led me to a “many-hats” office manager role at a tech startup that really launched my current career.
Can you share the details on your career path and what were the critical moments that got you to where you are today?
The varied experience I had in roles and the different types of people who I worked with set me up for a lot of growth. It gave me a level of confidence that I would always be able to figure it out even if I didn’t know how to do it in the beginning.
My role in facilities included a lot of written and verbal communication with a wide audience of people at different levels and in different roles (teachers, administration, parents, vendors, etc.), which really grew my skills in knowing how to change the way I communicated depending on who, how or where the conversation occurred. The experience also taught me to acknowledge and invest in ensuring that the “do-ers” are not forgotten – in communication and celebration and in providing context around what they are being asked to do. This applied to a team of maintenance workers making a school hum, and in later roles, a team of engineers building software to serve the business and its customers, and everyone in between. My work has also included a lot of crisis management, which I have used in every role since.
When I landed at my first startup, this was really a jumping off point for me. Startups are built around giving people the opportunity to grow and expand their roles - we’re trying to get a lot out of a little! So I took that office manager role and grew it into benefits management, talent management, customer program management and product management. I worked with an amazing group of people who recognized my natural strengths and weren’t afraid to throw a new challenge at me, and who were willing to answer every question I could ask as I learned along the way. I learned there is strength in being open about what you don’t know and demonstrating that you are eager to learn. The relationships created here have stayed with me throughout my career.
I have taken all of those skills and used them in each step in my career. The non-linear evolution of my education and career has, at times, been an insecurity for me, but it has allowed me to always feel comfortable with the unknown and not necessarily seeing the path before me. This has helped me at the macro level in my life and at the micro level of approaching projects, organizational change and crises with my day to day.
I have also been very lucky that I have worked at more than one organization that had a mission that aligned with my own values and views about the world. This is something I have prioritized as I have progressed through my career. It is also a major reason why I am at EF now. EF’s mission to educate and bring people together to foster understanding and tolerance through travel and cultural experiences connects so many important dots from my own experience and values.
What is your current role and responsibilities?
I am currently the VP of Product at EF Education First. I manage a team of product managers and UX designers. In concert with the engineering team, we are responsible for both the internal operational systems needed to run both our domestic and international tours products as well as our customer facing digital experiences for our student focused tours products. I am always looking at how we can best bring value to the business (understanding our business goals and how we work, so that my team can drive value) and my day-to-day activities include being organizationally focused. We are a central department in an international company, so I spend a lot of time communicating and ensuring that expectations are set, and we have alignment and prioritization across the business. The product managers on my team are driving individual requirements and work so I meet with them regularly to ensure that their work is aligned with cross-business strategy and share whatever context I can to help them drive their work successfully and keep their teams engaged.
I spend a lot of time thinking about and influencing how we work cross-functionally, supporting communication and strategic alignment with my team and with stakeholders in other parts of the business, and driving a product management culture across the business so that we are always thinking critically about what questions to ask, what we are really trying to achieve and refining our goals and approach as we learn.
Looking back, is this where you thought you’d be professionally? Was it always your goal to be in this position?
My end goal was never a particular position, but to be in a role where I helped bring people together. to work effectively and efficiently, to work with smart people who were excited about their mission and to be in a position to help solve interesting puzzles. And to always feel like there was room for me to grow. Even now, I can see lots of different positions that would foster those goals but my current role definitely supplies all of them combined with interesting challenges.
Though my career experiences have led me to this role, my life experiences have brought me to EF. Both my personal and professional experiences have allowed me to work and interact with all different kinds of people and recognize the value of different perspectives. This has shaped my personal and career growth and this very much aligns with EF’s mission. I also feel like I am living our mission every day on a much smaller scale by bringing different perspectives together and fostering communication all while serving the larger mission of helping spark mutual understanding by uniting people across borders and culture.
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 there are many different flavors of product managers - some more visionary, some more operational. I think a key factor, whichever way you lean, is elevating your communication skills, remembering that the people on your team are key to your success and that how you talk about things - the words you use - matters. I have often thought of the product manager as the translator – between different perspectives, between the business users and technology or the external and the internal. Elevating your communication skills will help get people to buy in, will build confidence with your team and help you drive both the vision and the execution. Because communication and translation is so important to me, it feels great to work for an organization that is also helping people learn languages to communicate in a different way, and offering free resources to help people on their learning journey.
Don’t be afraid of exposing what you don’t know. You don’t have to be the person who knows it all and sometimes, even if you think you have it figured out, you should ask questions anyway because you may learn something.
Do the dirty work. Especially as you start out - but even later - you will learn by digging into the details. You will build camaraderie and confidence if you show that you aren’t afraid to get your hands dirty. Pitch in where you can, it will always come in handy in a different way later on.
Find an advocate. This could be a mentor or a colleague, your manager or a team member.
What are the most important skills that you need to do your job well?
For my career trajectory, it really goes to the basics: Listening skills. Communication skills. Translation skills.
What do you find most interesting/rewarding about your work? What’s most challenging?
The most interesting is also the most challenging. Seeing a cross-functional team hum and creating the right solution for the right problem. Taking the messiness of human dynamics, pressures of hard problems and tight timelines and making sense of them - creating a system that allows for creativity and precision. This includes coaching and (hopefully) inspiring. EF fosters the type of collaboration that is required to achieve the right results for the business. And also empowers everyone in the business to step into their strengths and influence the end result and the process along the way. We are a large organization that values thinking creatively. And we aren’t afraid of trying something scrappy to learn our way into the long term solution. Having spent most of my career in startups this was something that was important to me when I joined EF.
What is your proudest professional accomplishment?
This is a hard one, but all of my proudest moments are reflected in the teams I have worked with. A recent major accomplishment, here at EF, that I am very proud of has been helping to drive through an (ongoing) series of challenges related to business reaction, customer experience and operational systems in reaction to COVID. We amped up our cross-team and cross-functional collaboration. We maintained laser focus on top priorities and “up-leveled" our communication. We delivered meaningful solutions to the business at lightning speed.
Are you involved with any professional organizations outside of the company? Volunteer work?
Not currently in any in depth. I have participated with WITI in the past. I am definitely seeking new opportunities for this type of work right now.
Q&A
What do you enjoy doing in your free time?
I have 2 sons, ages 6 and 2, who keep me very busy. I love hiking with them and just experiencing their little brain gears turning. I also enjoy cooking, reading, and have done a lot of DIY construction over many years so I guess that is still something I enjoy :)
How do you manage stress?
I really benefit from running, or other forms of exercise where I just have to focus by unplugging and getting out in nature whether in the woods or by the ocean.
How many cups of coffee do you have in a day?
1 cup of decaf. I love coffee but only have caffeine on rare occasions.
What's one of your favorite places in the Boston?
The Arnold Arboretum in Boston.
Any book or podcast recommendations? (professional or fun)
- I am definitely a true crime podcast junkie. So any and all.
- Song Exploder
- Heavyweight
- The A16Z podcast
- This is Product Management
- Hidden Brain
And more. When I was a kid I loved listening to the radio and would find these radio dramas to listen to so podcasts continue this for me. I love podcasts.
What advice do you have for recent college graduates?
There is no job below you. You can learn something from everything you are tasked with. You may just have to figure out what it is. Sometimes it won’t be the big cool challenge you are looking for but they are all steps towards that.
