Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Mary Kaufman, SVP Product at Takeoff.
Where did you grow up and how would you describe yourself as a child?
I grew up in Wethersfield, CT, the 5th of 7 children in a very athletic and competitive family. That sense of competition spanned academics, athletics, and board or card games. My high school sports were swimming, gymnastics, and track & field - participating in sports was a big part of my youth.
What did you study in college and what was your first job out of school?
I majored in Engineering Sciences at Dartmouth College - because it’s a liberal arts college, I actually graduated with a bachelor of arts in Engineering! I found that I enjoyed the entry level course in each of the engineering disciplines, but was less enthusiastic about subsequent courses, which made me realize I didn’t want to be an engineer. So I got a job as a consultant, figuring that would allow me to decide what industries & types of jobs I enjoyed most. I had done some programming in college and so joined Computer Partners, which had been recently acquired by CSC, to do systems consulting.
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 early on that I liked being able to understand the business and their needs and help translate that to system needs. I liked that more than solving the tough architectural or technical problems associated with implementing a system. So that put me on the path of business analyst or business architect as we called it in those days, and eventually included more management consulting type work.
I remember the first supply chain-related project I was on - it was like a light bulb went on and I was just so intrigued and enthused about how computer systems can completely transform a physical operation like warehousing & distribution. Compared to a financial services project I had been on earlier, it just felt so real, so tangible and impactful. And as I continued in my career, I’ve found that working with operational products is more appealing to me than consumer-facing products.
The final inflection point was joining CSN Stores, which then became Wayfair. I found the thrill of working at a startup - no bureaucracy, nobody who is just “punching the clock” - just a fun, fast-paced environment with a little bit of chaos thrown into the mix, and building something that everyone believed in. I was hooked from the start.
What is your current role and responsibilities?
I currently head up the Product organization at Takeoff Technologies. Our solution provides retailers with the most cost-efficient way to fulfill their online grocery orders, using automated, hyperlocal Microfulfillment Centers. The product team listens to clients, keeps a pulse on the industry, partners with our operations teams who are working to drive success at clients, and works with our engineering team to bring continuous improvements to our solution.
Looking back, is this where you thought you’d be professionally? Was it always your goal to be in this position?
This position didn’t really exist until somewhat recently - along with the Agile methodology came a new type of role so I certainly didn’t aspire to it!
To be honest, after spending 15 years in consulting, and much of that time on the road, I was well and truly burned out by the time my first child was born. So I actually thought at that time that I was retiring to be a full-time mother, never to go back to the workforce. And I spent 7 years in that occupation. But when my younger child started school, I realized I missed exercising that part of my brain and the feeling of professional accomplishment so I looked around for a local company and found Wayfair. It was serendipity that I happened upon them and it was definitely the most rewarding chapter of my career to date. It also led to my move to Takeoff Technologies as I was recruited by a former colleague. So I think I’ve been lucky more than planful in my career.
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?
Get comfortable with data - be able to pull your own data & do your own analysis. Zoom out occasionally to make sure you understand how your work is aligned to your organization’s objectives & strategy. Make sure you take a step back and articulate to yourselves & others why you are building something and how you will know if it’s successful. Finally, get good at saying No but in a way that convinces people that No is the best answer at this time - prioritization is everything in product.
What are the most important skills that you need to do your job well?
Communication skills are crucial - both listening and then translating what you’ve heard to other audiences and then circling back to replay. It took me a while to learn that you can’t over-communicate as a product manager.
What do you find most interesting/rewarding about your work? What’s the most challenging?
When I was growing up and we would talk about professions, my dad always said that the most important thing, more than money or prestige, was that you enjoy what you do at work.It was such great advice, and I’ve kept that forefront in my mind as I reflect on changes I want to make in my career. I find that working with a small team, using data to get insights & figuring out how a product investment can help solve an operational problem is what gets me out of bed in the morning. Several times in my career, I’ve ended up in a place where my team & area of responsibility had grown to be so large that I felt disconnected from the problems they were solving and as a result felt less fulfilled by my job. At that point, the ego and external forces are telling you that you should be striving for more & bigger but I recognize that it doesn’t make me happy. So each time, I’ve swallowed my pride and taken a portion of my remit and spun it out to somebody else. In many cases, it’s been somebody on my team who I’ve seen grow & become ready for the challenge, and that’s been rewarding as well.
What is your proudest professional accomplishment?
There were so many at Wayfair and I feel so fortunate to have been part of that growth story. My team helped launch their Castlegate 3PL business along with the Wayfair Delivery Network. Both were such audacious goals and we accomplished them so quickly - it got me hooked on the power of a small group of talented people to do amazing things. That’s what ultimately attracted me to Takeoff; the desire to make an outsized impact with a small team of really smart people, and to have fun doing it.
Are you involved with any professional organizations outside of the company? Volunteer work?
Pre-pandemic I was more involved in CSCMP and Boston Product Managers Association, but I find I have limited appetite for virtual events after spending all day working remotely. When my children were still in elementary school, my husband and I were active in volunteering and supporting their school in various ways.
Q&A
What do you enjoy doing in your free time?
I picked up tennis several years ago and I’ve really enjoyed playing recreationally and on a USTA league team. It's one of the only sports I’m still getting better at. My husband and I snowboard and our kids ski, so we try to do that a few times a year though not as often as we used to. And we’ve always enjoyed playing cards & board games after dinner - I’m amazed that as teenagers my kids are still enthusiastic participants.
How do you manage stress?
Exercise, games, reading, and crosswords are all stress relievers for me - any activity where you need to be present and focus helps to destress. I also love taking my dog on long walks in the woods. Getting in some cardio while being out in nature is the best medicine.
How many cups of coffee do you have in a day?
Usually 2, but each is about half skim milk. When it’s summer and I’m drinking iced coffee, I am tempted to sip all day long but I have to stop myself after about 2pm because then I don’t sleep well.
Any book or podcast recommendations?
I’ve been in the same book club for 20 years and we’ve read so many great novels - a recent favorite was The Night Tiger by Yangsze Choo. During the pandemic I started to listen to podcasts during long walks or runs. I always enjoy RadioLab, Freakonomics Radio, and The Future of Everything (Stanford Engineering).
What advice do you have for recent college graduates?
Find a job that sounds interesting to you and see where it takes you. Remember the job you will love 20 years from now might not exist today so just build your skillset out and learn as much as you can. So many career opportunities come from people you know or have worked with in the past, so keep in touch with those people you’ve enjoyed working with.
