Send a three-touch win-back email series to expired trials

Pull every trial account that expired in the last 90 days without converting. Build a three email sequence: day 1 asks what got in the way, day 4 shares a short setup checklist for the exact feature they never touched, day 9 offers a 14 day extension with no card required. Send it from a real rep's inbox, not a no reply address.

Why it works: Most trial drop offs are a setup gap, not a fit problem, so removing friction converts more than a discount does.