The company
A fundraise, pivot, acquisition process, board decision, critical hire, or a team that needs to change. We clarify the real choices and decide what deserves your attention now.
Coaching & Advisory
A partner for consequential chapters.
I coach founders through the decisions, transitions, and pressure that come with building a company—and becoming the leader it needs.
Start a conversationThe work
Most founders come to me in the middle of something.
The next move isn’t obvious, the stakes feel personal, or the way you’ve always operated is no longer enough. Our work usually moves across three connected areas.
The role
The job has changed underneath you. We work through cofounder dynamics, difficult conversations, delegation, focus, and how to become the leader the next chapter requires.
The person
The company isn’t the only thing carrying weight. We make room for confidence, identity, energy, family, and the question of how to perform without losing sight of what matters.
How I work
Coaching, with context.
You don’t need another person handing you a playbook. You need space to think clearly, someone willing to ask the hard question, and a partner who understands the weight of the decisions in front of you.
I start as a coach. We slow down, separate signal from noise, and get underneath the problem you walked in with. I’ll notice patterns, challenge assumptions, and help you hear what you already know but may not be ready to say out loud. You remain in the driver’s seat.
When it’s useful, I bring direct perspective from operating, investing, board work, and seeing similar moments across more than 100 companies. Sometimes that means a question. Sometimes it’s a framework, feedback on a deck or investor update, preparation for a difficult conversation, or an introduction that can move something forward.
The point isn’t to make the decision for you. It’s to help you make a better one—and build the capacity to navigate the next decision with more clarity and confidence.
What clients say
“Building a company comes with both shiny highs and rough, ugly lows. Dillon was with us through all of it, never shying away from uncomfortable conversations and always asking the tough questions. He’s everything you’d want on your team: grounded, consistent, and iterative.”
Selected clients
Salesforce · Techstars · Y Combinator · Ada CX · Quanta · Brev.io · Wrangle · Synch · Clockwise · Workramp
The partnership
One ongoing relationship, built around the work in front of you.
There’s no curriculum and no performative homework. We establish what matters, create a rhythm, and use each conversation for whatever is most alive and consequential.
- First conversation
- A 45-minute introduction and a live taste of the work.
- Deep dive
- A 90-minute opening session to build context and clarify our focus.
- Ongoing rhythm
- Two 60-minute sessions each month, guided by what matters now.
- Between sessions
- Phone or text support when something time-sensitive comes up.
I keep my roster intentionally small so I can bring real energy, context, and attention to every partnership. When helpful, we can also bring a cofounder into the room.
Begin here