Context
A Series A Jakarta SaaS company had grown from seven founding employees to 65 in 18 months. Five of the original seven were still there. Equity vesting cliffs had passed for all of them in Q1 2022. The founding CTO, the founding head of design, and the founding head of customer success each held equity worth, on paper, between $400k and $1.2M.
Decision
The founder treated the post-cliff window casually. There was no retention conversation, no top-up grant, no role-evolution discussion. New senior hires from Singapore and Indonesia were brought in above two of the three founding leaders, with no explanation of how scope or compensation would change for the originals.
Consequence
The CTO left in May 2022 to start a competing company. The head of design left in July to join Grab. The head of customer success left in September after being told her scope would shrink. The product roadmap stalled for nine months. Two existing enterprise customers churned because they had been promised features the leaving team had been building.
“The cliff date is the deadline for a conversation, not the conversation itself.”
— the lesson, in one line
Lesson
The cliff date is the deadline for a conversation, not the conversation itself. Map every founding employee's cliff date and have the retention conversation 90 days before — about scope, equity refresh, and the next chapter. Not after.
What most retellings miss
Every founding employee whose equity vested at the same moment is a coordinated departure risk. Founders rarely map the cliff calendar in advance.
The Aire angle
Aire tracks the cliff dates and the retention triggers so you do not lose load-bearing people to your own calendar.
Sources
HR Asia case studies are editorial analysis of public reporting and on-the-record interviews. They are not legal advice and do not reflect the views of the companies covered.
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The anonymized Indonesian founding-team case study on HR Asia is the most useful 6 minutes I've spent this month. The cliff date is the deadline for a conversation, not the conversation itself. Have the retention talk 90 days before, not after. https://hrasia.co/cases/founding-team-collapse
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