I’m Sara Hicks, an executive coach for startup founders and technology leaders. I coach founders, CEOs, and product, design, and technology executives navigating the complicated parts of building companies and leading people.

My coaching is grounded in more than 20 years as an operator. I’ve built products and teams from zero to one, co-founded and led a venture-backed startup, navigated an acquisition, and served as a Chief Product Officer inside a much larger company. I’ve experienced many of the transitions I now help leaders navigate.

Sometimes the challenge is organizational: your company is growing faster than your leadership practices, you have too many direct reports, your executive team isn’t working, or you need to make a difficult decision about a person or strategy.

Sometimes it’s more personal: you’re having trouble letting go, you’ve lost confidence in a decision, you’re exhausted, you’re becoming the bottleneck, or the role you’ve grown into no longer feels like the one you signed up for.

Usually, it’s both.

Coaching gives us a confidential place to figure out what’s really happening, separate signal from noise, and decide what you want to do next.

My approach combines more than 20 years of operating experience with storytelling, design and visual thinking, writing, meditation, psychology, and even a hint of spirituality. Together, we examine both the organizational challenge and the personal patterns influencing it. We unearth narratives that might be holding you back, get clear on where you’re going and why, and develop practical experiments that fit you rather than forcing you into a standard coaching formula.

Who I work with

Most of my coaching work is with founders and senior technology leaders, particularly:

Startup founders and CEOs building from zero to one and scaling themselves as their companies grow
Venture-backed founders navigating boards, investors, hiring, and organizational change
Product and design leaders developing product strategy, shaping roadmaps, aligning go-to-market plans, and guiding teams from idea to launch
Leaders stepping into VP, CPO, CDO, or broader executive roles, or strengthening how they lead in an existing role
Executives navigating an acquisition or the transition into a larger company
Leaders wrestling with delegation, accountability, conflict, burnout, or difficult people decisions
Women, LGBTQIA+, and other underrepresented leaders navigating environments that weren’t necessarily designed with them in mind

You don’t need to fit neatly into one of those categories. I care much more about the problem you’re trying to solve than your title.

What we can work on

Every coaching relationship is different, but some common areas we might explore include:

Founder and executive transitions
Board management, communications, and planning
Job and career transitions
Business planning, product strategy. and organizational clarity
Team design, communication, and decision-making
Feedback, conflict, and difficult leadership situations
Executive presence and confidence
Org design, hiring, and staffing
Burnout, boundaries, and sustainable performance
Other personal, professional, or organizational challenges you want to explore

How this works

Together, we establish goals and metrics for success, then we develop a plan to get you where you want to go, and then we make things happen. I’m an advocate of nonviolent communication, inclusive language, and continuous feedback. I’m not a fan of assessments, values exercises, jargon, and unnecessary rigmarole. I focus on experiential, organic, and experimental progress toward your goals. There is no average person, so there isn’t an average process that works for everyone.

We generally meet twice monthly, usually for 3 or 6 months to start, via Zoom, phone, or in Los Angeles, CA (where I live). In between sessions, you can reach me via email, text, or phone. It’s that simple. A lot of our magic might happen in between our sessions, as we will often share ideas and concerns asynchronously in docs and emails.

I work on a sliding scale, meeting you and your company where you are, whether your company is paying or you’re paying your own way. I’ve never turned anyone away for budgetary reasons, so please don’t let cost keep you from starting the conversation.

I also reserve a small number of spots for free coaching, especially for folks from underrepresented backgrounds. We’ll start with a free introductory conversation and talk about what feels workable for you.

I’ve been on the other side of the conversation.

I co-founded Reaction Commerce and served as its CEO, raising venture capital and building the company from the beginning through its acquisition by Mailchimp. After the acquisition, I eventually became Mailchimp’s Chief Product Officer and Product Advisor. Earlier in my career, I held product and design leadership roles at companies including Etsy, Media Temple, Yahoo!, and GeoCities.

I’ve experienced the ambiguity of zero to one, the pressure of being a founder and CEO, the challenge of building an executive team, the relationship between founders and boards, the uncertainty of acquisition, and the very different dynamics of leading inside a large organization.

That doesn’t mean your experience will be the same as mine. It means you don’t have to spend half the session explaining what these situations feel like.

Today, I’m the founder and CEO of HappyHQ, a founding partner and executive coach at The Intentional Organization, and co-author of The Intentional Organization: A Leadership and Management Guide. Here’s a longer bio, along with talks, interviews, and published writing.

Managing and leading people has been one of the most rewarding parts of my career. It’s also been the most challenging and lonely part of my job. Having to always be on can be daunting, and needing to have all the answers is tiring.

These issues have been just as true in early-stage, fast-growing startups as they are in larger, more mature companies. On top of it all, being a female founder in tech has often exacerbated the feelings of loneliness and frustration. Having my own coach and a small group of mentors to talk through those feelings and concerns continues to be incredibly valuable for me.

A little of how I think

My writing includes a coaching conversation about whether to pivot, a hiring mistake I made as CEO, and working through a difficult employee situation. In Accountability Needs Friction, I explore how a useful coaching conversation can challenge our assumptions about someone else’s ownership. You can find more in the executive coaching archive.

Are you ready?

The best way to see if working together is right for both of us is to set up a time to chat. Find a time below, answer a few questions, and I’ll get back to you within 48–72 hours to confirm our meeting, or I’ll ask a few follow-up questions. It helps if you can take a few moments to think about what brings you here and what you want to get out of working together. Your answers to the questions will help us frame our initial conversation so that we can get the most out of it.

If you’d rather connect via email at first, please get in touch. I appreciate your patience.

Executive Coaching for Founders & Technology Leaders