Top 10 Learnings about Free Trials with Tomasz Tunguz

In this segment, Jason M. Lemkin presents survey data visualized as a heat‑map that cross‑references four contract types (usage‑based, month‑to‑month, annual, multi‑year) with annual contract value (ACV) bands ranging from $0 to $150K. The key observations are: • In the $15K‑$50K ACV range, 80% of respondents use annual contracts. • Mid‑market companies overwhelmingly favor annual contracts. • Small‑to‑medium businesses (SMBs) predominantly choose month‑to‑month contracts (about two‑thirds). • Enterprise customers mainly opt for multi‑year contracts (about two‑thirds). Lemkin interprets these patterns to recommend that most companies, regardless of size, should pair a free trial with an annual contract, because a statistical analysis shows no significant difference in free‑trial conversion rates across contract types. Even for SMBs where month‑to‑month is common, an annual contract does not hurt conversion performance.










