Leadership coaching

Leadership coaching from someone who’s been there

I understand ambitious founders and operators. Whether you're a new executive or more seasoned, whether you work at a large organization or a startup, I've been there and get what you're going through.

You don’t have to be a founder to operate like one. My clients include startup CEOs, C-suite execs, and ambitious leaders inside large orgs, all leading with founder-level clarity, urgency, and ownership.

I don’t teach abstract leadership theory. I coach and teach from lived experience. I don’t just “hold space.” I push, challenge, and clarify. I don’t separate strategy and leadership. With me, they’re the same conversation. I can help you own the room, because I’ve built the room.

I am likely to challenge you and take you outside your comfort zone, but I will also be your fiercest ally. If these experiences sound like what you might be looking for in a coach, we might be right for one another.

Coaching that comes from lived experience

  • Conventional coaching can be soft and impractical. Working with Kieran is the opposite: practical, strategic, and driven. She's a world-class leader and it's amazing to have her in our corner as we scale Kit.

    Nathan Barry
    CEO and Founder @Kit

  • As a former CEO, Kieran brings a rare and invaluable practical perspective to her coaching, one rooted in lived experience. What sets her apart is her ability to both listen with deep empathy and challenge me with clarity and conviction. Exactly what I asked for in a coach.

    Keri Higgins-Bigelow
    CEO and Founder @livingHR

  • There are good people, and there are winners. Kieran is both. She brings the rare combination of data chops and human insight to leadership, seeing patterns others miss and helping executives not just perform, but tell their own story. If you get the chance to be coached by her, count your blessings

    Roy Bahat
    Head @Bloomberg Beta

  • Because Kieran was a successful CEO herself, she is uniquely able to help me understand what CEOs are looking for from their people leaders. She isn't just a leadership coach. She is a leadership coach who is able to open up the window into CEO thinking and business strategy.

    Anthony Onesto
    Chief People Officer @Suzy

  • Kieran has been an integral part of our early stage success. I've worked with her on everything from structuring our sales process to fundraising strategy to hiring, and her experience building companies has been directly useful on all fronts. Most importantly, she's a person who is genuinely "in my corner" and whom I can trust and rely on for candid conversations in a safe space.

    Josh Schwartz
    CEO and Co-Founder @Phaselab

  • Kieran's lived experience as founding VC-backed CEO, data storyteller, chief evangelist and leader of people make her an exceptional coach for the next generation of founders. 

    Aileen Lee
    Founder @Cowboy Ventures

Schedule, availability, and fees

You’re looking for a long-term coach.

I take on a limited number of long-term clients at a time. When I commit, I really commit. The most effective coaching work happens when we can build a relationship over time. I've been working with my own coach since 2016.

We mutually commit to partnering for three months, six months, or a year, and we will meet in-person or virtually for an hour every 2-4 weeks depending on your goals. I am also highly available asynchronously and regularly provide deck feedback, help with hiring, product notes, and much more.

For these longer term arrangements, my coaching fee is between $1,100-$1,600 per session, depending on the length and frequency of our engagement. In some cases, I will consider startup equity for a portion of my coaching fee. I also offer discounts for leaders who have been traditionally underrepresented in their industries.

You have a hard business problem you need to solve right now.

I also offer short-term sprint contracts for clients with an acute business or leadership problem to solve. In these cases, you want to work through a specific problem with focus and dedication. In the last year, sprint clients have hired me for fundraising support, pricing and packaging support, AI consulting, hiring blitzes, offsite planning, and lots more.

For these engagements, I charge a monthly retainer of $5-10K depending on the particulars. In exchange, you get a lot of my time and very fast responses. We will meet weekly for four weeks. I am also highly available async to review material or offer other feedback. You can work with me in this way on a month-to-month basis.

Get in touch

Workshop, speaking, and coaching applications. Data story ideas. Nerdy things you recommend I read. Feedback on my website, the nerd processor newsletter, and especially my comics. Leave a note below!