Harvard in Tech Spotlight: Amy Rosenthal, Head of Product at FreeWill
By: Jess Li
Tags: Startup, Product, Entrepreneurship, Harvard, Social Impact

I spoke with Amy Rosenthal, Head of Product at FreeWill, a social venture that makes charitable giving easier than ever with a mission to move $1 trillion into high impact nonprofits.

Amy’s first exposure to product management was through her junior summer internship. She took on a role where she worked closely with sales to better understand customer and prospect needs and then worked closely with engineering to incorporate those insights. She enjoyed the cross functional nature of the role and has stayed in product ever since.

Amy worked at Context Optional (acquired by Adobe), Wayfair, Google, and Justworks prior to joining FreeWill as their first product hire in 2019.

Amy shared her advice for career growth, product leadership, and collaboration.

Optimize for happiness. Too often in our career decisions, we are pulled by societal expectations of what we “should” do whereas what truly matters is whether we enjoy what we are doing, a more meaningful metric that is different for each person. For Amy, when she graduated Harvard, product was not yet the incredibly popular space it is today. In hindsight, she stumbled into the field and stayed not because of societal expectations but rather because she truly enjoyed the work itself.

Share advice whenever you can. Founders and operators at early stage startups frequently face the same set of challenges. Sharing insights from your experiences can be incredibly helpful for others who are entering similar parts of their company building journeys and can save them hours, if not weeks, of work and roadblocks.

Amy and Jenny Xia Spradling, FreeWill’s founder and co-CEO, were both Harvard alums who lived in Currier and graduated a year apart from each other. Amy saw Jenny post on Facebook that FreeWill was looking for their first product hire and interested in hearing people’s advice on how to find and integrate product talent. At the time, Amy was an early product hire at another startup also based in NYC and decided to reach out to share her advice around growing product teams and product processes in early stage startups. The more they brainstormed together, the more Amy realized she was actually personally very interested in the role. These conversations then led to her actually joining the team soon after.

See your team as a product. Product managers are innately very execution oriented people but leading a team of product managers involves a very different skillset. When you are promoted to lead such teams, it is important to first realize and internalize that you will need to quickly learn and exercise a meaningful set of new skills. Instead of continuing to engage in individual contributor work, you need to learn to resource, train, delegate, and empower. Especially at a startup, many of the guidelines or guardrails around responsibilities are not yet written and much of it is developed by you as the leader as you learn and iterate. To this end, see your team as your new product and apply the same interpersonal, collaboration focused mindset to equipping and engaging your team to reach their highest potential.

Collaborate as soon as possible. Oftentimes, our instinct can be to go at it alone or be independent in the initial exploration of a promising idea. But more often than not other team members have valuable and diverse information, experiences, and perspective to help you in ideation and execution. Put yourself out there, reach out to team members, and collaborate as early as possible and sooner than you may think you need to.

Diversify your communication channels. Especially in a remote world, it is crucial to over communicate. Instead of just leveraging one channel, utilize all of them depending on your message and audience. Some team members are most responsive and can more effectively digest communications via email; others may prefer Slack or a Zoom meeting. Be inclusive in your communication style and ensure proper documentation through over communicating and leveraging a range of channels to share your message.

Identify the discrepancies between internal and external stakeholder understandings. When Amy started in each new product role (many at startups in very different industries), she spent a substantial amount of time listening to customers as well as internal team members to better understand their points of alignment and misalignment and dove deep into these latter facets as a starting point for informing product strategy.

Work closely with customer support. At FreeWill, customer support is actually a part of the product team, which Amy has found incredibly valuable. Seeing each customer question, challenge, and message has really helped her better understand and shape the product strategy.

Learn the most valuable things first. When exploring a new field, it can be tempting to immediately dive in, but it is often helpful to first ask others for advice on what to read to better pull the signal out from the noise. Amy has found the Women in Product community very helpful in providing resource recommendations as she has made each industry and role transition. Advice from others who have been there before has helped her prioritize what to read or learn.

Surround yourself with people who challenge you. Looking back, Amy’s favorite part of Harvard was being a part of friend groups and communities with people who had such diverse talents and interests, academically, personally, and professionally. This setting and the friendships that have been created from this richly diverse environment have shaped Amy’s growth mindset ever since. She enjoys, appreciates, and grows from each interaction that challenges her existing beliefs and assumptions and shares new perspectives.