Build organizations that do more, with less.
I work with founders and senior leaders to master the disciplines of High-Leverage Leadership — doing more with smaller, sharper teams.
Built on Experience — Proven in the Real World
At Groupon, I led a small, curated team tasked with building the company’s global merchant payments platform, serving 35 countries and billions in transactions during one of the most chaotic growth periods in tech history.
We weren’t the biggest team, but we were one of the most effective. While the company accelerated at breakneck speed, we built calm inside the storm — systems, culture, and clarity that let us move faster precisely because we stayed small.
We built leverage, not layers.
That experience changed how I lead, and now how I work. I help founders and senior leaders apply the same principles to their own organizations: building clarity, culture, and focus that scale.
Appreciation
High-Leverage Leadership
for Organizations
Small teams can now do what once required entire departments. But technology doesn't create that leverage — leadership does.
High-Leverage Leadership is an organizational engagement for leadership teams that are growing and want to stay sharp doing it. We work together over 6–12 months, with regular team sessions and ongoing support between them. The focus is practical: building the clarity, culture, and focus that let your organization move faster without adding complexity.
Leaders create leverage — not layers.
Clarity
Shared direction. Everyone knows what matters, why it matters, and how decisions get made.
Culture
How people show up when no one's watching. Values that drive behavior, not just decorate the wall.
Focus
Protecting what matters from what's merely urgent. The discipline that keeps good teams from becoming busy ones.
Investment & Commitment
Organizational engagements are structured as quarterly retainers, typically ranging from $15K–$40K depending on team size and scope. This includes team sessions, leadership workshops, and ongoing support between sessions. I work with a limited number of organizations at a time to ensure depth and impact.
Strategic Partnership
for Founders & CEOs
At a certain point, the company starts growing faster than you can. The pressure builds, the decisions multiply, and everyone looks to you for answers.
This is where a strategic partner makes the difference. It's a confidential, ongoing engagement — regular 1:1 sessions, plus availability when something can't wait. No agenda, no worksheets. Just a high-context thinking partner who's been inside the room where those decisions get made.
What founders need most isn’t advice — it’s space to think.
Think Clearly
Space to work through the decisions that are too sensitive for the board and too complex for the team.
Decide with Conviction
Cut through the noise on what actually matters — strategy, people, priorities.
Lead Through the Hard Parts
The shift from builder to CEO is real. This is the work no one else in the room can help with.
Investment & Commitment
Strategic partnerships are structured as ongoing monthly retainers, typically ranging from $5K–$10K per month. This includes regular 1:1 sessions, ad-hoc strategy calls, and confidential thought partnership when you need it most. I work with a small number of founders at a time.
Private Advisory
for Senior Leaders
At some point, the ceiling you're hitting isn't about skill. It's about how you're leading.
I work 1-on-1 with senior leaders over 6 months or more — bi-weekly sessions, with space to work through what's real, not just what's presentable. The focus shifts based on where you are, but the through-line is always the same: getting clear on how you lead, and closing the gap between where you are and where you want to be.
When your leadership is clear, everything else aligns.
Clarify Your Identity
Who you are as a leader, what you stand for, how you want to show up.
Expand Your
Influence
Building credibility and trust beyond your immediate function.
Close the Gap
Between the leader you are and the leader the moment is asking for.
Investment & Commitment
Advisory engagements typically start at $500 per month for bi-weekly sessions. Most leaders commit to at least six months to create meaningful momentum. I work with a limited number of individual clients at a time to ensure focus and impact.
How It Works
Remote or In-Person
Most engagements are conducted remotely, with optional in-person sessions for team workshops or strategic planning. I work with leaders across North America and internationally.
Engagement Structure
Organizational engagements run quarterly, with bi-weekly or monthly team sessions. Strategic partnerships and private advisory are 1:1, structured around your rhythm.
Who's a Good Fit?
You're leading through a moment that demands more from you as a leader. You value clarity over complexity and want a thought partner who understands operational reality — not just theory.
I’m Todd Webb
I spent more than 30 years inside fast-moving organizations — leading engineering teams, shipping products, and figuring out in real time what actually makes a team work.
At Groupon, I led the team that built the global merchant payments platform. Thirty-five countries. Billions in transactions. We did it during one of the most chaotic growth periods in tech history, with a team that stayed small on purpose.
That experience is where I learned what leadership under real pressure looks like — and what separates teams that scale from teams that fracture.
Before Groupon, I spent decades leading and building across startups and established companies. Different industries, different stages, same patterns. What works isn't complicated. It's just hard to see when you're inside it.
Ready to lead with more leverage?
I work with a small number of clients at a time. If this feels like the right fit, let's talk.
Or just reach out: todd@toddwebb.co