An interview with Dan Storms about being the first product leader at a startup

Scaling decision-making is critical for startups to grow in size and organizational complexity. Unless we consciously decide to adjust how we make decisions as we shift into the next phase, it can become cumbersome or ineffective. James Trunk, VP of Engineering at Griffin talked with me about how they scaled decision-making at the Fintech startup.

We often believe that we need to have functional expertise to lead others but in my experience, that’s not true. We can lead without having discipline expertise – something Edwina Johnson knows well from her time as COO of Fintech startup Alloy where she built and managed a team with broad expertise.

Our conversation highlighted just how strong COOs are at working cross-functionally across an organization. Edwina – like the best of them – understands how to drive alignment around a common goal without using positional authority. There are so many lessons about collaboration and leading without functional expertise in this interview. I hope you enjoy Edwina’s wisdom as much as I did.

Kelly Port, VP of Product at Elsmere Education talked about her time as the EVP of Product Development and Commercialization at GutCheck leading the product from revenue decline to successful exit. We talked about the importance of curiosity for product leaders, how to realign the organization around a new product direction, and her advice for other product leaders who need to reinvigorate a stale product.

Sheree Atcheson, Group Vice President of Diversity and Inclusion at Valtech is the author of Demanding More. Sheree talked with me about her experience leading global teams. We talked about our shared belief about why the discovery process is so critical for new leaders in a business. We also talked about the importance of bringing others along, especially when in an organizational leadership role. That alignment is so critical. Finally, we talked about the need to have embedded ways to listen. This is so important for all leaders.

Leaders are often expected to be superhuman, which also means being infallible. But leaders are decidedly human. They get sick just like the rest of us. They also get diagnosed with serious and chronic illnesses. Having a disability at work can be challenging for anyone. Navigating chronic illness while also carrying the responsibility of leadership can feel overwhelming.

Meri Williams, CTO of Pleo talked with me about what it’s like being a CTO while navigating Ehlers-Danlos – a painful condition that can be debilitating. During our conversation we talked about how the limitations of a chronic illness impacted the way they saw themselves, how they changed their leadership style, and their wisdom for those who find themselves newly diagnosed while leading.

Leading at a startup is very different from leading at a growth-stage company or a large enterprise. When taking a leadership role, considering the phase of business is really important. David Yee, VP of Engineering at the New York Times spoke about his journey from startup exec to leading at a large company.

We talked about what the transition from startup founder to big enterprise leader was like, being an experienced leader in a new organization, and what it means to “do the right thing” as a leader.

Being a change agent CPO with Namrata Sarmah

Reorgs are tricky parts of organizational life. Allison McMillan, a Fractional VP of Engineering is an experienced leader who has worked at companies like GitHub, Forem and General Assembly. Throughout her career she’s been through many reorgs. We talked about what it’s like to lead during a time of high organizational change, building trust with new teams and how to plan during constant change.

The leap to director is often bigger than we imagine. We find ourselves with more responsibility and working at the organizational layer but also having to make sure the people doing the work are aligned. This can be challenging. I asked Sonal Mehta, Director of Engineering at Intuit MailChimp to share her experience navigating what I call the director sandwich. Sonal and I talked about how the role was different than she expected, managing expectations, the role of trusted advisors and so much more. If you’ve just taken on a bigger organizational role or support those who do, there are so many nuggets in here for you.

Kristen Foster-Marks, Technical Lead for the Technology Center of Excellence at Pluralsight has chronic condition PMDD. We spoke about how she takes good care of herself while leading, how she manages vulnerability and authenticity, and being a recovering perfectionist, something I think many can understand.

Shweta Saraf, Director of Platform Engineering at Netflix has worked in a variety of cultures at companies like Cisco, Equinix (formerly Packet), and Digital Ocean. We talked about helping leaders understand their impact on culture, how to ensure people feel heard, how she builds trust, and how she approaches a new team. I know you’ll find Shweta as insightful as I did.

I met Michelle O’Connor, VP Brand & Global Communications at TaxBit through the NYC Fintech Women. I coached her for over a year as TaxBit scaled. I was thrilled she wanted to be part of the series. We talked about how she dramatically reduced her # of hours of meetings, how she thinks about hiring and what she’s learned about guiding culture at scaling startups.

The leap from engineering manager to VP of Engineering while also being a co-founder can feel big. It can also feel like just the right challenge like in the case of Ana Rosas, Co-Founder and VP of Engineering at Valued. We talked about her early career aspirations, what made her take the risk to co-found an early stage startup and her advice for other founder leaders.

The last time David Jarvis was on the series, we talked about being a first-time CEO at Griffin, a startup in a highly regulated industry. Since then he had his first child and took some time off to be with his young family. I asked David to talk about his experience taking parental leave as the CEO of a startup. We talked about how the company handled his absence, how becoming a parent changed him as a CEO, and what advice he’d give CEOs considering taking parental leave.

With their position and responsibility, it’s easy to forget that leaders also go through hard times just like the rest of us. One of the things I really enjoy about Jenn Clevenger, VP of Engineering at Etsy is how much she embraces her humanity, inviting all of us to embrace our own. During our conversation we talked about how she finds balance in the midst of uncertainty, how she keeps perspective and how she thinks about leading others through difficult times.