Simon Wilson

Background

About Simon Wilson

Helping Business Owners Make Smarter Decisions, Faster Are you a business leader with big ambitions but feeling stretched too thin? Do you have challenges to navigate, opportunities to seize, and a team to lead—all with too little time? At The Alternative Board® (TAB), I empower business owners to make better decisions—faster and with greater confidence. Through peer advisory boards, you gain insights from other experienced leaders, step outside your ‘reality bubble,’ and tackle key challenges in a supportive, accountable, and dynamic environment. The result? Stronger decisions, a growing bottom line, and a more motivated team.(See our latest member survey for the evidence: Beyond facilitating peer boards, I provide one-to-one coaching to align business goals with personal aspirations, backed by TAB’s proven tools and global network. My expertise spans go-to-market strategy, sales, IT/SaaS, operations, and program delivery. I also provide fractional CXO capability in Operations, Sales or CEO positions. With 30 years of leadership experience in Finance and Technology—ranging from startups to global corporations—I now focus on helping SME owners in Gloucestershire and the Cotswolds build resilient, thriving businesses. I bring a strategic yet pragmatic approach, ensuring leaders take the right actions, at the right time, in the right way. I believe business should serve a purpose beyond profit, and that collaboration is key to long-term success. Outside of work, I’m a Director of a local non-profit providing housing and support for homeless men, helping them rebuild independent lives. I’m also an active member of Cirencester Baptist Church and a follower of Jesus. When I’m not working, you’ll find me cycling through the South Cotswolds or at Villa Park, cheering on the Villa! If you’re a business owner who wants to make better decisions, scale with confidence, and create a thriving organisation, let’s connect. I’d love to hear your story and explore how I can support you.