Coaching Services
Transformative Support for Technical Leaders
1:1 Executive Coaching
Tailored to your leadership journey
- Personalized coaching partnership
- Psychologically informed approach
- Focus on vertical development
- Regular sessions (weekly/bi-weekly)
- Email support between sessions
- Customized leadership practices
Leadership Team Coaching
Elevate your collective leadership
- Team dynamics assessment
- Individual and group coaching
- Systemic team development
- Strategic alignment workshops
- Communication enhancement
- Conflict as creative opportunity
Technical Leadership Advisory
Strategic guidance for founders
- Technical organization design
- Scaling strategy development
- Leadership team structure
- Investor/board communication
- Acquisition preparation
- Post-merger integration
The Coaching Journey
1. Discovery
We begin with a thorough exploration of your current leadership context, challenges, and aspirations. This phase establishes a foundation for our work together, identifying patterns, strengths, and areas for development that will shape your unique coaching journey.
2. Vertical Development
Together we create a personalized development plan focused on expanding your leadership capacity—not just adding skills but transforming how you make sense of leadership challenges. This vertical development allows you to navigate increasing complexity with greater clarity and effectiveness.
3. Integration
Through regular coaching sessions, we work to integrate new perspectives and capabilities into your leadership approach. Using psychologically informed models and practical exercises, you'll develop new ways of seeing and responding to the challenges you face.
4. Embodiment
True transformation happens when new insights become embodied in your leadership presence. We focus on sustaining and deepening your development, ensuring that your expanded capacity becomes a natural part of how you lead, even under pressure.
Coaching Methodology
My coaching approach integrates psychological depth with practical business experience. This unique methodology supports vertical development—helping you expand your capacity to lead in increasingly complex environments.
Human Potential Integration
Drawing from evidence-based coaching models that focus on unlocking human potential, I help you expand your consciousness to meet increasingly complex challenges. This approach recognizes that technical leadership requires both analytical excellence and human wisdom.
Psychological Frameworks
I incorporate insights from multiple psychological traditions—including Gestalt Psychology, Transactional Analysis, Internal Family Systems, and Existential philosophy—to create a holistic approach to leadership development that addresses both conscious and unconscious patterns.
Vertical Development Focus
While horizontal development adds knowledge and skills at your current level, vertical development transforms how you make sense of leadership challenges. This expansion of consciousness allows you to see more complexity, hold more perspectives, and make more nuanced decisions.
Technical Leadership Experience
My personal journey through the startup lifecycle—from early-stage growth to successful exit—informs my coaching with practical insights into the unique challenges technical leaders face. This lived experience creates a foundation of understanding that purely theoretical approaches cannot provide.
Who I Work With
Technical Founders Stepping into Leadership
For technical founders transitioning from hands-on building to leading teams and organizations. I help you develop the leadership mindset and skills needed to scale your company while staying true to your vision and technical values.
- Balancing technical depth with leadership breadth
- Building and leading diverse, high-performing teams
- Communicating vision to non-technical stakeholders
- Making strategic decisions amid uncertainty
CTOs and Technical Leaders Scaling Up
For technical leaders facing the challenges of rapid growth. I help you develop systems thinking and organizational design skills to build scalable technical organizations that maintain innovation while increasing in size and complexity.
- Scaling engineering teams and technical processes
- Transitioning from coding to strategic leadership
- Building and developing technical leadership teams
- Balancing technical debt with business velocity
Leaders Navigating Critical Transitions
For founders and executives preparing for or going through acquisitions, exits, or major organizational changes. I provide support through these complex and often emotionally challenging processes, helping you lead with clarity and purpose.
- Preparing your company for acquisition or investment
- Navigating complex negotiations and due diligence
- Maintaining team cohesion during transitions
- Planning your next chapter post-exit
Experience & Impact
8+ Years Coaching Experience
Working with 100+ founders & executive leaders through startup to scale-up (Series C+) to exit, helping them navigate the full spectrum of technical leadership challenges
Proven Leadership Track Record
Successfully led and exited Space Ape Games (acquired by Supercell), scaling to 130+ team members and $70M+ revenue while maintaining an award-winning culture
Technical Leadership Depth
Former CTO experience helping scale products to 80M+ users at Mind Candy, navigating the technical and leadership challenges of hypergrowth
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."
"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."
"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."