Jane Portman is the co-founder and CEO of UserList, a B2B SaaS email platform built specifically for behavior-based onboarding and lifecycle email. She’s also the host of the Better Done Than Perfect podcast. In this episode we dig into how to actually convert free trial users to paid – the data setup, the email mechanics, and where most founders get it wrong.
Timestamps
- [00:01] Why activation beats filling the top of funnel
- [00:03] The real stages of solving the activation problem
- [00:05] Moving off hardcoded emails to a proper tool
- [00:08] Why behavior data – not button clicks – is your foundation
- [00:10] Planning lifecycle segments before touching your dev
- [00:13] How a feature check-in email sequence actually works
- [00:17] Selling paid before users are active – the biggest mistake
- [00:23] How many emails is too many – and day-parting to reduce overlap
- [00:28] Plain text vs designed emails – and what sender name to use
- [00:33] Pausing newsletters during onboarding and KPIs to track