Why did you decide to become a mentor?
I’ve been tutoring and teaching courses since I was young. In junior high I helped to tutor seniors in basic computer use. In high school, I worked part-time at a hebrew school, and later got to be a TA for AP Economics. Throughout college I tutored students in math classes and economics. Mentoring grew pretty naturally out of the work I was already doing in tech as well. While a Product leader at its core, my specialty in APIs required me to establish and manage Developer Relations teams as well. I both mentored PMs under me, and developer advocates who over time, consistently become successful PMs with my guidance. This eventually expanded into teaching and more formal mentoring. I've taught more than 15 Product Management cohorts and over 300 students, helped develop curriculum for popular PM bootcamps, and co-authored Duke University's Product Management Certificate. I've also mentored founders through accelerators including Techstars, Alchemist, and Heavybit over the years. What keeps me doing it is that mentoring is very different from simply giving advice: you get to watch someone develop their own judgment over time. The goal isn't for a mentee to make the decision I would make; it's to help them develop a framework that lets them make better decisions themselves.
How did you get your career start?
My route into Product Management was relatively traditional on paper, but there was a lot of luck involved. I studied Computer Science at the University of Illinois and then went to Carnegie Mellon for my MBA, focusing on Product Management and Strategy. At the same time, I had developed what I've described as a somewhat irrational obsession with APIs. In college, I was fascinated by the idea of the "web as an operating system" and spent a lot of time experimenting with whatever web APIs I could find. In 2008, I found a Craigslist posting for a small startup… called Box (Box.net at the time). What caught my attention was that it was the first Product Management job I'd seen specifically focused on APIs. I joined as one of roughly the first two dozen employees and became the Product Manager for the Box platform. From there I helped build the developer platform from the ground up: the APIs, developer portal, documentation, partner integrations, and eventually the Developer Relations team and a community of more than 15,000 developers. That experience largely set the direction for the rest of my career. I've been working at the intersection of Product Management, APIs, integrations, and developer ecosystems ever since.
What do mentees usually come to you for?
There's usually one of two themes. The first is career-related: Product Managers trying to break into PM, move into leadership, become more technical, evaluate their next role, or navigate a difficult situation inside their organization. The second is product-related: founders and product leaders working through product strategy, product-market fit, APIs, platform strategy, marketplaces, roadmaps, or how to build and scale a Product organization. Because I've spent much of my career working between technical and business teams, I'm particularly useful when the problem sits somewhere in between the two. I don't like treating mentorship as a generic curriculum. I generally start by understanding what someone is actually trying to accomplish and what's preventing them from getting there. Then we break the problem down, identify the questions that matter, and establish concrete next steps. Sometimes that means reviewing a roadmap or API strategy; sometimes it's preparing for a Product interview, thinking through an offer, or dealing with an organizational challenge. One of my MentorCruise mentees described the process well: rather than simply telling her what to do, I helped her identify the critical questions she needed to answer about her API strategy. That's generally what I'm aiming for—giving someone frameworks and questions that remain useful after our mentorship ends.
What's been your favourite mentorship success story so far?
It's hard to choose one, because I've had the opportunity to mentor people at very different stages—from students trying to land their first Product role to founders trying to build a company. Some of the most rewarding outcomes have been people I've taught or mentored making the transition into Product Management and eventually building careers at companies like Google, Amazon, Meta, Uber, and Slack. I've also advised startup founders whose companies went on to raise significant funding or successfully exit.
What are you getting out of being a mentor?
While I mostly do it because I like helping others, mentoring has actually helped me to improve my communication skills, by positioning myself in different discussions and environments, to face different challenging topics outside of the workplace. It also gives me exposure to a much wider range of problems than I'd encounter in any single job. I've worked with companies and mentees across different industries, stages, business models, and organizational cultures. That keeps me from assuming that whatever worked at Box, Tradeshift, DocuSign, or Salesforce is automatically the right answer somewhere else.
