“I got a Google Sheets list of the top 100 best-performing consumer subscription companies in the world and I emailed every CEO, every head of growth. Then I hopped on Zoom calls with them and I flew to wherever they were in the world. I literally sat behind them in their office and looked at how they bought Instagram ads.”

Cold-Outreach to Top-100 Subscription CEOs — Sit in Their Office Watching Instagram Ads

Cliff built Speechify's ad playbook not by hiring an agency but by personally shadowing the people already doing it at scale — founders of Reflectly, Blinkist, Dollar Shave Club, Grammarly, and Whoop. His tactic: cold email the top 100 subscription CEOs, get one call, show up in person. He learned at Reflectly that stories convert better than posts and polls drive more engagement than static images — insights that shaped years of Speechify ad strategy.