5 Critical Phases of Building Your SaaS Sales Machine: Jason Lemkin + Harry Stebbings

Summary

SaaStr co-founder Jason Lemkin and investor/podcaster Harry Stebbings updated their deep-dive guide on building a SaaS sales machine, refreshing a 20+ minute playbook for 2025 that outlines five critical phases for creating a first sales team. The piece details practical steps—hiring and role sequencing, compensation and quota-setting, go-to-market motions, process and tooling, and metrics to track—to move startups from founder-led selling to repeatable revenue. For SaaS founders and early-stage CEOs, the framework clarifies when to invest in people versus process, how to de-risk scaling, and what KPIs signal readiness to expand field sales, directly impacting speed to scale and cash-burn efficiency.