Startup CEOs
Example · Board of 3A key investor wants me to fire my VP Sales. They underperformed Q3 but the team trusts them. What do I do?
Chief of staff
This one needs a board: The CEO, The Strategist and The CFO. The CEO holds the through-line on company strategy and stakeholder trade-offs. Each researches alone first, then they react to one another — and on a decision, two of them take opposed sides.
The CEOChief Executive Officer
The StrategistCompetitive Expert
The CFOFinancial Controller

Asked first
If you could do only one thing this quarter, is this it?
YesOne of twoProbably not
The board’s call
Hold the line at a 15% discount with extended terms, not 40%.
A 40% discount becomes the new floor for every renewal. 15% with multi-year and quarterly billing protects gross retention.

The CFO disagreed
“If this customer is >15% of ARR, the leverage flips — model that scenario explicitly”
Board of 3 · up to 135 credits on the card · an example, not a recorded run









