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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.
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Visit https://funnel-vision.ai
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