The Courage to Lead

In the quiet moments between decisions, we find the truths that shape our leadership. I walk alongside technical founders and CTOs as you navigate the profound personal transformations that accompany your startup's growth.

"The real voyage of discovery consists not in seeking new landscapes, but in having new eyes." - Marcel Proust

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Key Leadership Challenges

Beyond Technical Mastery

The most sophisticated technical systems are often easier to debug than the human dynamics of leadership. Your next level of growth requires more than technical knowledge—it demands expanded self-awareness and the ability to create environments where others can excel.

Clarity in Complexity

Leadership effectiveness begins with understanding yourself. Having built and led technical organizations through multiple growth stages, I help you recognize your strengths, blindspots, and the patterns that shape your leadership. Our work creates the clarity needed to lead authentically and make better decisions amid increasing complexity.

Experience-Informed Guidance

My approach is grounded in lived experience—from writing code to leading engineering teams to navigating successful exits. Combined with formal psychological training, this background allows me to provide guidance that bridges technical understanding with the human elements of leadership that ultimately determine success.

Vertical Development

As your company grows, so must your capacity to lead. I help you develop not just new skills (horizontal growth) but new ways of making sense of leadership challenges (vertical development). This expanded consciousness allows you to handle competing demands, make difficult trade-offs, and create organizational cultures where values guide decision-making at all levels.

Leadership Transformations

"Toby's unique blend of technical expertise and psychological insight helped me navigate the transition from technical founder to CEO. His coaching was instrumental in developing my leadership style during our Series B fundraising."

— Alex K.

CEO & Co-Founder, AI Tech Startup

"As a CTO scaling my engineering team from 15 to 80 people, Toby's guidance was invaluable. He helped me develop systems thinking and emotional intelligence that transformed how I lead my organization."

— Sarah M.

CTO, FinTech Scale-up

"Working with Toby through our acquisition process was transformative. His experience having been through exits himself provided practical insights that helped me navigate complex negotiations while maintaining team morale."

— James T.

Founder, Acquired SaaS Company

Begin Your Leadership Evolution

The journey to becoming the leader your company needs starts with a single conversation. Book a complimentary consultation to explore how coaching can support your growth and help you navigate the challenges ahead with greater clarity, purpose, and effectiveness.

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