Executive Coaching for Founders, CEOs, and Senior Leaders

At a certain level of scale, the decisions carry more weight and the room gets quieter — fewer people tell you the truth, and old instincts strain against new complexity. This is what executive coaching is built for: not advice from the outside, but a confidential thinking partner who has actually sat in the seat. I'm David Dressler. I spent over a decade co-founding and scaling Tender Greens from one restaurant in Los Angeles to a 1,200-person, $100 million business, through a successful exit. Today I coach founders, CEOs, and senior leaders at the inflection points where growth or their own leadership style has become the friction. Most clients come by referral, because the work is quiet and the results speak for themselves.

When executive coaching is worth it

Most leaders at this level don't need another opinion — they need a place to think. Good executive coaching matters when the stakes are high and there's no one inside the organization to think out loud with: a board member has an agenda, a co-founder has a stake, your team is watching. A coach sits outside all of that. This isn't about fixing you — you're already capable. It's about removing the drag: unexamined patterns, avoided conversations, decisions you keep circling. Clear those, and everything downstream moves faster.

Coaching from the seat, not the sidelines

There's a difference between a coach who has studied leadership and one who has lived it. I'm not handing you a model from a book — I've made payroll when it was tight, held a culture together through fast growth, and sat with the weight of the final call. That's what I bring, and why the founders and CEOs I work with trust the room we build. This matters most on decisions a framework can't reach: whether to keep a loyal executive who's stopped growing, how to raise capital without losing yourself, when your gut and your data disagree. Those conversations define a company, and they're the ones I'm built for.

Who I work with

I work with a specific kind of leader: founders who've grown past the version of themselves that started the company, CEOs carrying more scale and visibility than before, and senior leaders stepping into new weight. That includes founder coaching for people scaling something built from nothing, CEO coaching for leaders managing a board, a team, and their own bandwidth at once, and executive coaching for women navigating environments not designed with them in mind. It also includes entrepreneurs whose company has outgrown improvisation, and seasoned executives who simply want a sharper mirror. The industries vary; the pattern is the same — a capable leader at a threshold who'd rather not figure it out alone.

How the coaching works

I keep it simple. We meet twice a month, one on one, with extra support between sessions when something can't wait. It runs on a monthly retainer adapted to your rhythm, not a rigid program with a fixed finish line — no long-term contracts, just compounding value that keeps clients coming back. Sessions happen in person where geography allows and online everywhere else. This is one-on-one coaching in the real sense: not a course or curriculum, but a relationship built around your actual decisions in real time.

What changes

The result is leadership that feels clearer, steadier, and more sustainable as complexity grows. You start seeing around corners before problems arrive, stop carrying every decision alone, and finally have the conversations you've been avoiding. Clients describe faster execution with less panic, stronger relationships, and a way of leading they can sustain long-term. That's the point of coaching done well — not dependence on a coach, but a leader who's grown into the size of the moment.

Frequently asked questions

If any of this sounds familiar, you already know it's worth a conversation.