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SaaS Go-to-Market: Why Selling to Startups Failed

Episode 370 Published 2Β years, 5Β months ago
Description

Josh Ma and his co-founder interviewed 46 engineers before writing a single line of code for Airplane. Their SaaS go-to-market strategy started strong - but selling to tech startups stopped working when budgets tightened in 2022.

In this episode, Josh reveals how Airplane pivoted its SaaS go-to-market from Silicon Valley startups to fintech and healthcare verticals, reaching 7-figure ARR. You will learn why founder-market fit matters more than TAM, how Google Ads landed their first five largest customers, and why cold outbound emails produced zero traction.

Airplane is a platform for engineers to build internal tools. The company has raised over $40M from Benchmark and has a team of 20 people. Josh credits their go-to-market strategy shift to vertical targeting and word-of-mouth growth.

πŸ”‘ Key Lessons

  • 🎯 Founder-market fit filters out bad ideas early: Josh used two tests - "Can I spend 10 years on this?" and "Do customer conversations give me energy?" - to select Airplane's SaaS go-to-market direction.
  • 🀝 Interview 40+ prospects before writing code: Airplane talked to 46 engineers about frustrations and workflow gaps, which led them to the script-running problem that became their core product.
  • πŸ“‰ The startup-selling SaaS go-to-market playbook broke in 2022: A $30K contract negotiation took six months with a startup, forcing Airplane to pivot to non-tech verticals with less constrained budgets.
  • 🏒 Target specific verticals for a horizontal go-to-market strategy: Fintech and healthcare companies had regulation and compliance needs that created stronger demand for internal tooling.
  • πŸ’° Google Ads can bootstrap early enterprise deals: Airplane used paid search to land its first five largest customers at $20K ACV, making acquisition break-even at one deal per month.

Chapters

  • Introduction
  • Josh's motivation and what Airplane does
  • How the Airplane product experience differs from competitors
  • Business size - 7-figure ARR, $40M raised, 20 people
  • Josh's background as CTO at Benchling
  • How the Airplane idea came about through exploration
  • Idea filters and founder-market fit
  • Why founder-market fit matters more than TAM
  • How to run pre-build customer interviews
  • Entering a crowded market and why competition is overrated
  • Build versus buy - selling to developers
  • Shipping the MVP in four months
  • Getting the first 10 paying customers
  • Why Josh wishes he shipped the MVP sooner
  • Word of mouth as the primary growth driver
  • Content marketing strategy for developer tools
  • Why Google Ads worked despite common wisdom
  • Why cold outbound emails failed
  • Shifting from startups to fintech and healthcare verticals
  • Messaging a horizontal product for specific verticals
  • Lightning round

Resources

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