Go upmarket, or stay with small teams?
Work · Board of 3Our project tool sells to teams of 5 to 20 at $12 a seat. Three companies with 500+ people have asked for SSO and an annual contract. Do we go upmarket, or stay focused on small teams?
Chief of staff
Your board is seated: The Strategist, The Sales Leader, The Skeptic. They read the brief first, then research, then argue it out.
The StrategistCompetitive Expert
The Sales LeaderChief Revenue Officer
The SkepticRisk Assessor
The board’s call
Serve these three as design partners, not as a new market: build SSO, sign annual contracts, and decide on upmarket after six months.
Three inbound requests are a signal, not a segment. SSO for paying design partners costs one feature; going upmarket means security reviews, procurement and a sales team before you know whether large accounts expand.

The Skeptic disagreed
“Design partners turn into roadmap owners. Three large logos can quietly steer a small-team product. Put the limits in writing.”
Example · Board of 3 · about 95 credits


