Simon Wakeman

Experienced operational leader specialising in working with founders to grow resilient, high-performing businesses.

Simon Wakeman Photo

Simon's Bio

With more than 25 years of experience as a COO, MD, and founder, Simon Wakeman helps ambitious founders navigate the challenging transition from start-up to scale-up.
Career Highlights
  • Led UK-listed technology services group TPXimpact plc as COO, scaling revenue from £31.5m to £83m and headcount from 361 to 700 in just over two years.
  • Grew digital transformation agency Deeson Group from 15 to 40 people, achieving 95% revenue growth in four years with net profit consistently above 29%.
  • Significant buy and sell-side M&A experience, including integrations.
  • Co-founded and launched conversational AI business GreenShoot Labs (now OpenDialog.ai), successfully exiting to AIM-listed The Panoply plc.
  • Professionally qualified in change management, coaching, OKRs, marketing and communications.
  • Developed the B3 framework® in 2023, providing a toolkit to help founders build brilliant businesses.
Notable Client Work
  • Successful long growth strategy and implementation engagements with multiple US and UK-based agency and consultancy businesses.
  • Took on a failing 30 person SaaS platform business as fractional COO, developed and implemented new business strategy, major restructuring and putting a new leadership team in place to take the business forward sustainably.
  • As fractional Transformation Director in a tech agency, Simon designed and implemented new business and people processes, building trust with the team and delivering operational efficiencies quickly.
  • Team coaching and facilitation delivering united, high-performing teams with clearly defined roles and goals. 
Growth Strategy and Implementation
Progressive Organisational Design
Transformation and Change Management
Commercial and Operational Optimisation
Enabling Founder and Leadership Succession

Simon's expertise

Working with Simon

Simon's Personality
Simon describes himself as collaborative, calm, diligent, challenging and proudly generalist.
Simon's Ideal Client
Simon’s ideal client is a senior leader or organisation that is:
  • Ambitious but struggling to lead their business to the next stage
  • Wanting to take a structured approach to growth
  • Seeking to improve leadership performance
  • Values a blend of strategic thinking and rapid iterative implementation

Why Work With Simon
  • 25+ years of diverse experience across sectors and business types
  • Strong leadership track record of growth in MD and COO roles
  • Experienced fractional executive, consultant, advisor and coach

How Simon Can Enhance Your Business
  • Help identify root causes of underperformance and address them fast
  • Design new structures, processes and systems to enable growth
  • Taking a generalist perspective to problem solving
  • Working with leaders and teams at all levels to deliver improvements and change

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