Speaker

Jason M Lemkin

Jason M Lemkin

Founder of SaaStr — the largest B2B SaaS community, conference, and content platform — and co-founder of EchoSign (grown to $100M ARR, acquired by Adobe, where he became a VP of web services). SaaStr Annual draws 10,000–12,000 founders and operators a year; the Europa event in London runs alongside it. Co-author (with Aaron Ross) of From Impossible to Inevitable (~100,000 copies sold). Known for: tactical hiring frameworks for early sales teams, sales–product budget allocation models, contrarian advocacy for freemium and long free trials, the ‘VP of Free’ concept, and the ‘be kind’ ethos. Active on Twitter/X (@jasonlk) and LinkedIn (~260,000 followers).

Key ideas

  • Hire two reps, not one — interview ~30, hire on the single filter ‘would I buy my product from them?’, and A/B-test humans the way you A/B-test features.
  • VP of Sales timing — never before two reps consistently hit quota; insist they still carry a bag. Build the org on the rules of eight span-of-control heuristic. (See notes for the full sequence.)
  • Hire someone whose last product was harder to sell — the highest-leverage hiring heuristic; an easier-product background arrives without the skills your product demands.
  • Give sales a fixed quarterly engineering budget (~10% of story points) to force force-ranking; stress between product and sales is healthy, its absence means you are not in enough deals.
  • The VP of Free — the absent role that defends the non-converting free base in a PLG org; only founders and product will hold the brief.
  • Compounding is the only thing that matters in B2B — anti-compounding moves (dark patterns, unearned price rises, forced annual contracts, weaponised customer success) are permanent costs; for low-end products, obsess over churn.

Episodes in this wiki