For founders & CEOs
Executive Coaching for Startup Founders
Building a company is personal. I know firsthand.
Founding a company changes as the company changes. At first, you’re talking to customers, shaping the product, recruiting, pitching investors, and fixing whatever broke overnight. Then you’re hiring leaders, working with a board, and delegating things you still care deeply about, all while continuing to build the company.
I’ve lived this.
I co-founded Reaction Commerce and served as its CEO from zero to acquisition. We raised venture capital, built a distributed team and open-source community, changed strategy, hired executives, made mistakes, worked with a board, and eventually sold the company to Mailchimp.
Today, I’m the founder and CEO of HappyHQ, an AI-native company, and I coach startup founders navigating many of the same questions. Our work gives you space to think about your company and grow into the leadership it needs next.
What founders bring to coaching
There isn’t one founder problem, but there are patterns I see again and again:
The company
- Am I working on the right thing?
- Should we keep going or change direction?
- Where could AI help us build a better company, and what would we need to change?
- My board wants one thing and I want another.
The team
- Who should my first executives be?
- I have too many direct reports. What should the organization look like?
- My co-founder and I aren’t aligned.
- Someone who was perfect for the company two years ago isn’t working now.
You as a founder
- When do I stop doing this myself?
- What should I delegate to people, to agents, or keep doing myself?
- How do I hold someone accountable without taking their job back?
- I can’t tell whether I’m burned out or whether I don’t want to do this anymore.
- The company needs a different CEO than it needed at the beginning. Can I become that person?
These questions look organizational from the outside. Often they’re also deeply personal.
“We’ve covered topics ranging from fundraising and product vision to decision-making and navigating difficult conversations. She encourages me to turn ambiguous, tough, and varied problems into tangible option paths and focus on what I can control.”
From founder to CEO
One of the strangest parts of building a company is continually becoming qualified for a job you’ve never done before.
The skills that make someone an exceptional founder, including urgency, conviction, involvement in everything, and willingness to break things, can eventually collide with the skills required to lead a growing organization.
The goal isn’t to stop being a founder. It’s to become more intentional about when your founder instincts are helping the company and when they’re getting in its way.
That’s work I particularly enjoy.
“Sara gave our founders a trusted, confidential space to work through the issues keeping them up at night—from cofounder conflict and difficult pivots to fundraising, product strategy, and go-to-market challenges.”
How I coach founders
I’m not there to run your company for you or give you a founder playbook.
I ask questions, challenge assumptions, notice patterns, share relevant experience when it’s useful, and help turn ambiguity into something you can examine.
For a founder’s perspective on that balance of directness and empathy, read Charlotte Swead’s experience of coaching while building Sell Savie.
Sometimes we leave a session with a decision. Sometimes with a difficult conversation you need to have. Sometimes with an experiment. Occasionally the most useful outcome is realizing that the problem you arrived with isn’t actually the problem.
My job isn’t to make you more like some imaginary ideal CEO.
It’s to help you become more intentional about the founder and leader you want to be.
“She can get very tactical when that’s what you need, but she also pushes you to step back and ask bigger questions about who you want to be as a leader and what you want from your career.”
Work with me
I work with founders from early-stage and zero-to-one companies through venture-backed growth, acquisition, and the transition into larger organizations.
“I highly recommend Sara to anyone looking to grow as both a leader and a person. She supported me through many of the challenges of being a first-time founder and CEO, and we worked together through very different stages of my company, from the early days as a pre-revenue, bootstrapped startup to building a business with a loyal team, predictable revenue, and venture backing.”
If you’re wondering whether we’d work well together, start with a free introductory conversation.
Schedule a free introduction, or read more about how coaching works.
Related reading
In When to Hire Your First VP of Product, I share what I learned from both sides of the handoff: recognizing when you’re the bottleneck, defining what a new leader will own, and making room for them to lead.
I wrote about a hiring mistake I made as CEO and how I coach founders deciding whether to pivot. In Accountability Needs Friction, I reflect on the expectations I hadn’t made clear before asking a leader to take more ownership. If your next transition involves selling your company, see coaching through acquisition.