The habits that made you a high-performer are often the same ones that stall your team at scale. I am a sounding board for C-Suite leaders navigating the transition from individual grit to high-leverage leadership.
Rooted in the messy reality of scaling to 1,200 employees, $100M in revenue, and a successful exit.
At a certain level of scale, sheer effort stops delivering a return. The decisions are heavier, the stakes are higher, and the grit that got you here starts to create more noise than signal. You don’t need to be "fixed" and you certainly don't need more tasks on your list. You need the space to find your own judgment again.
I’m David Dressler. I spent a decade co-founding and scaling an organization to 1,200 employees and $100M in revenue. I’ve lived the high-pressure (and often lonely) reality of the inflection points where a business outgrows its leader’s original habits.
I don’t bring a playbook or a set of formulas. I bring the steady judgment earned from sitting in that chair. Our work focuses on resolving the friction between the relentless demands of your business and your actual capacity to lead it. The result is a steadier presence and the ability to think clearly when everyone else is looking to you for the answer.
I don’t use long-term contracts; I rely on compounding value. I work this way because our partnership should be a source of relief, not another obligation. Most of my clients stay for years because the clarity we build becomes an indispensable part of how they lead.
For founders and executive leaders.
You need a confidential sounding board for the challenges that can’t be socialized with your board, your team, or your family.
We focus on the heavy-lift decisions and the internal capacity required to make them. It is about ensuring your judgment keeps pace with scale so you can see the plain reality of the business even when the stakes are highest.
For leaders and their teams.
As a business scales, the implicit ways of working that once felt like a superpower start to create organizational drag.
I work with leadership teams to identify where communication has broken down and rebuild the structural agreements needed to move as a single unit.We resolve the underlying friction so the team can return to focused execution.
For the redefining moments.
Stepping back, stepping up, or moving on are the most high-stakes transitions a founder will ever face.
Drawing on the reality of my own $100M exit, I help you navigate the psychological and strategic shift of separating your identity from your organization. We ensure your legacy remains intact so you can move into your next chapter with confidence, not regret.
“Working with David gave me clarity, confidence, and practical direction at a crucial moment in my founder journey. His insight came from real experience, not theory, and made an immediate difference. He challenged my thinking, encouraged me in a way I hadn’t experienced before, and gave me a simple assignment that materially moved my business forward.
I’m deeply grateful for his presence, honesty, and support. I’d recommend David to any founder who wants a coach who has truly been in the arena and knows how to help others grow with strength and compassion.”
— A.P., Founder & CEO
“Stepping into a senior leadership role at a fast-moving creative company was daunting. David quickly became a trusted sounding board. He listens deeply, gets to the heart of issues, and draws on real-world experience.
With his guidance, I’ve built clearer processes, stronger relationships, and a more confident, balanced way of leading. Our meetings, team energy, and results have all taken a noticeable step forward.”
— P.M., COO/CFO
“David guided me from founder-doer to CEO by helping me build processes, empower my team, and sharpen my focus. At the same time, his calm, values-based approach helped me stay confident in my instincts during fundraising and growth.
Having someone who’s been through operations and capital raising himself, and validated my gut from real experience, is incredibly powerful. The result for me was faster execution with less panic and more conviction.”
— D.G., Founder & CEO
“We needed our management team to have a trusted advisor as we entered the next phase of growth with a new partner. David’s balanced approach brought trust, collaboration, and new perspective to the team — and peace of mind to the board.”
— J.S., Managing Partner
“David took two skeptical groups and helped us come together in a meaningful way. We explored what was working, what wasn’t, and learned how to engage with each other honestly and productively.
The experience was connective and surprisingly energizing. Beyond solving immediate issues, it helped us clarify the kind of company we want to be and the principles that will guide us forward.”
— R.O., Chief Development Officer
If you’re at an inflection point and need a sounding board, let’s see if there is a fit.
