From C grades to CEO

In this episode, Leo, founder of Playbook Agency, discusses his entrepreneurial journey and the evolving landscape of sales. Starting his career in SaaS sales, Leo progressed from an SDR to Head of Sales at Salesflow. His turning point came during an incubator program where he realized many bright minds lacked fundamental outbound sales and lead generation processes. This led him to start a consultancy, coaching sales professionals on effective processes, which later evolved into a lead generation agency utilizing AI tools like GPT and Clay.

Playbook Agency currently serves three main Ideal Customer Profiles (ICPs): founder-led businesses (around $1M revenue) needing sales acceleration, small sales teams (1-3 people) requiring 'leads as a service,' and Series A to Series C SaaS companies (and increasingly traditional B2B) with existing sales and marketing departments. For the latter, Playbook focuses on driving efficiency through automated list building, enablement, and sophisticated data strategies for account tiering and ad targeting.

Leo emphasizes that a crucial skill for Go-to-Market (GTM) engineers is not just technical proficiency with tools like Clay, Claude, and Perplexity, but also a deep understanding of the *why* behind their efforts. He highlights that knowing the industry and product inside out, and asking curious questions, transforms sales calls into valuable consultations. Major challenges facing sellers today include the increased volume needed to generate quality leads, the importance of robust data foundations (clean CRM data), and effectively harnessing insights from call transcripts to refine prospecting.

Looking ahead, Leo predicts sales will bifurcate into two distinct paths: highly technical sales roles, especially in software, and relationship-led sales for other sectors. Buyers are becoming more self-educated through Product-Led Growth (PLG), shifting the sales engagement point later in the funnel. To stay ahead, sales leaders must proactively engage customers by understanding their pain points early and increasing buyer confidence throughout their journey. Leo’s personal motivation stems from overcoming early academic struggles and finding purpose in building a highly valuable, data-driven service that addresses tangible business problems, ultimately aiming to be the leading GTM operations company in London and New York.