From 7 to 150 People: How Sean Griffith Scaled SimpleTexting and Now Ships Features Overnight with AI

The Operating System Show · Aug 4, 2026 · 28m

Sean Griffith joined SimpleTexting at seven people and helped grow it to about 150 in under four years, through an acquisition, without a dedicated sales team for most of that run. He is now CEO and cofounder of Truffle, a candidate screening platform for small and mid sized businesses. We cover what actually made that scale work, why EOS was the unlock at 50 people, and the overnight release pipeline his team runs now that would have taken three or four people a month before. ## In this episode * Hiring conservatively and putting the cash into SEO instead of ad spend * Settling on an…