Find Your Heading.

“The wind and the waves are always on the side of the ablest navigator.”
— Edmund Gibbon

Empathy. Compassion. Direction.

tack, verb, nautical: to change the course of a sailing vessel by steering it into and through the wind.

FounderTack is a boutique, highly specialized coaching practice specifically that focuses on helping founders and senior executives navigate the challenges involved in managing uncertainty and developing as authentic, effective leaders.

FounderTack is led by Kevin O’Brien, an exited founder with over a decade of CEO experience. We focus specifically on helping address and resolve critical operational challenges that early-stage companies and leaders face:

  • Navigating complex dynamics and transformational change

  • Managing and resolving conflict with grace and direction

  • Addressing market changes, downturns, and pivots

  • Scaling up (or down) teams while maintaining authenticity, empathy, and outcome

FounderTack focuses on helping you manage uncertainty well.

Learn more

Kevin O’Brien

Principal

Serving as a leader is an all-encompassing challenge. It’s incredibly rewarding, but it also challenges you to your core. Every conflict and moment of lost conviction comes home to roost when you are in “the seat”.

I am a former technology CEO and founder, with nearly 25 years of experience working in, building, founding, leading, and selling startups. I have deep expertise in the venture-backed world, having raised over $30m USD, leading multiple companies, and managing complex exits.

I coach entrepreneurs as they navigate these waters.

Every client-coach relationship is unique, but the framework I use helps with uncovering the goals, assumptions, reactions, and experiences that inform the decision processes that you use to lead your company. By engaging in a sustained dialog, I can help you evaluate what was previously accepted without question, identifying and keeping what works, and changing what does not.

I hold a BA in Philosophy from the University of Massachusetts Amherst, and outside of work I am a lifelong martial artist and avid sailor. I have served as a mentor, advisor, and board director for dozens of companies, helping founders and CEOs navigate fundraising, team dynamics, product market fit, early stage go-to-market issues.

Reach Out

Deciding to work with a coach is a significant decision, and it’s natural to have questions about the process, the outcomes, and the experience.

We’re happy to chat, with absolutely no pressure or sales pitch involved. Reach out and we’ll be in touch shortly.