From C grades to CEO

In this episode of the Funnel Vision podcast, host Richard Bounds sits down with Leo to unpack his journey from being a C-grade student to becoming a founder and CEO. Leo shares how he stumbled into sales, scaled from SDR to Head of Sales, and ultimately built Playbook Agency by turning real-world sales experience into a go-to-market engine. The conversation dives deep into ICP clarity, AI-driven outbound, go-to-market engineering, and how modern sellers must adapt to an increasingly informed buyer. Chapters (00:00) Introduction and How Richard and Leo Met A chance meeting, a conversation over beers, and the start of the discussion. (00:40) Entering Sales by Accident How Leo stumbled into sales as his first commercial role at Sales Flow. (01:17) From SDR to Head of Sales Scaling quickly inside a growing startup and leading a sales team early in his career. (01:40) The Drive to Start a Business Why Leo always wanted to build something of his own. (02:07) Antler and the Entrepreneurial Wake-Up Call What Leo learned from being surrounded by consultants, bankers, and founders. (02:50) Learning Sales the Hard Way Making mistakes, learning on the job, and why curiosity beat formal sales training. (03:22) Mastering ICP and Industry Knowledge Why knowing the market and customer problems mattered more than frameworks. (04:39) Founder Fit, VC Thinking, and Bootstrapping The contrast between bootstrapped businesses and venture-backed expectations. (05:41) Building Playbook Agency How a consultancy evolved into a lead generation agency and then into AI revenue implementation. (06:04) Defining the Ideal Customer Profile Breaking down Playbook’s three ICPs, from founder-led businesses to Series A–C SaaS companies. (07:56) SDRs, Efficiency, and AI Enablement How AI helps modern sellers handle volume, research, and personalization. (09:01) What Is a Go-To-Market Engineer? Why technical skill without commercial understanding does not work. (10:01) Using AI Tools in Practice How Playbook uses Clay, OpenAI, Claude, and Perplexity together. (11:48) Why Not Just Do This In-House? The challenge of consistency, adoption, and scaling AI workflows across teams. (13:10) The Biggest Challenges Facing Sellers Today Pipeline pressure, higher volume requirements, and underused internal data. (14:28) Harnessing Call Transcripts and Sales Data Turning conversations into insight for better prospecting and ICP refinement. (17:10) The Future of Sales Roles Why sales is splitting into relationship-led sellers and highly technical sellers. (19:08) Buyer Awareness and Late-Stage Engagement How buyers now contact sales much later in their decision process. (21:16) Turning Time Saved into a Clear ROI Story How Playbook quantifies value beyond just closed deals. (23:01) Data Providers and Sales Tooling Choices Why the right data source matters more than having every tool. (25:08) Automation vs Personalisation When AI-driven outreach works and when it fails. (26:26) Long-Term Vision for the Business Becoming the leading go-to-market operations company in London and beyond. (28:18) Go-To-Market vs RevOps Where responsibilities overlap and why RevOps can no longer ignore GTM engines. (31:09) From C Grades to Confidence How education struggles shaped Leo’s motivation to prove himself through building. (32:47) Using AI to Analyse Won Deals Why analysing transcripts from closed deals is an untapped advantage. (35:37) A Deal He’s Most Proud Of Applying Playbook’s own principles successfully in a recent win. (37:38) Where to Find Leo Connecting via LinkedIn and continuing the conversation. Follow Funnel Vision for more conversations with sales leaders and founders. Visit https://funnel-vision.ai Curvo AI: https://curvo.ai