Back to Blog

Leading & Growing Through the Seasons

“Work takes on new meaning when you feel you are pointed in the right direction. Otherwise, it’s just a job, and life is too short for that.” – Tim Cook

Being a technical founder poses particular challenges to scaling in your role as CEO. Scaling a company is challenging. Leading through that scale as your role as CEO is also constantly changing adds to the waves of change that a leader must move through on the arc of growth. In particular, founding CEOs leading through the early startup to scaling years often report that from season to season it feels as if they’re leading a completely different company in terms of what’s required of them. 

When the founding CEO has technical expertise as someone who has been intricately involved in the building of the product and the technology, that can bring its own set of unique challenges for the technical founder who finds themselves scaling with the organization. If a CEO is highly technical and instrumental in building out a company’s product from the beginning, it may be especially hard to navigate a shifting relationship to that product and technology as the company grows. 

How does that CEO balance business responsibilities, fundraising, business development, organizational development, building out a leadership team, and the list goes on, while continuing to lead and guide the product and technology vision? How does the CEO’s job description and priorities shift as the company scales?

In today’s podcast conversation, my colleague Andy Crissinger sits down with Evan Drumwright, CEO of Dextrous Robotics to talk about these very questions. Evan speaks to the transitions he’s made, what’s worked for him and what hasn’t, and how he’s been able to be the CEO that Dextrous needs him to be. “I am the steward for this whole organization that I’m building and, as long as I am in that role, then I’m going to do what’s best for that organization which may even include getting rid of myself,” Evan notes. And while he clearly asks himself ‘What is my role as CEO? What is my responsibility to the company?’ he also allows himself five percent of his time to be spent on the things that give him joy.



Embracing Leadership as a Reluctant CEO This essay is written by one of our first alums from our CEO Bootcamp, Sooinn Lee, CEO of LocoMotive Labs. Last fall, Sooinn also spoke at TEDxBayArea Women in a…
Connect. Think. Lead. Adapted from the forward I wrote to a friend’s new book… Connect. Think. Do. I’d first gotten the call, an inquiry call for coaching, two weeks previous. In a follow-up…
Up and to the Right I have a chai; he has a cappuccino. We sit outside, at the metal mesh patio tables, as the coffee house is about to close. “I can’t decide the path:…



The Reboot Podcast with Jerry Colonna, Team Reboot, and Startup Leaders

Check out the episodes

Social Media

Follow us on:


Follow our Medium publication for reflections on leadership and resiliency.

Subscribe to Medium