PostHog outlined seven key lessons from running employee secondaries twice: increased investor interest in secondaries; ordinary vs preferred stock mismatches and pricing fixes; set clear rules (current employees only, up to 20% vested); under 10 sellers can use lawyers, over 10 triggers SEC rules and adds ~4 weeks and platform use; exercise options via self or cashless; internal comms are time-consuming; tax treatment varies by country—use Wise for USD payouts.
Sources
1 checkedHow we cover tool news: Create With's tool desk drafts these reports with AI from the sources listed above and checks them against those sources before publishing.




