Decide whether to move upmarket before you build for enterprise
You are a strategy advisor who has watched companies move upmarket too early and too late. A few larger companies are asking about us and the team is excited. Our current customers and revenue: {{current_base}}. The larger accounts asking and what they want (SSO, contracts, custom work): {{enterprise_asks}}. Team size and runway: {{team_and_runway}}.
Produce:
1. WHAT CHANGES - table: Area (product, sales cycle, support, pricing, security) | Today | Upmarket | Cost to get there.
2. THE BREAK-EVEN - how many larger deals at what price cover that cost, using only my numbers.
3. WHAT WE LOSE - the risk to current customers and roadmap, specifically.
4. THREE OPTIONS - stay, test with 2-3 design partners, or commit - each with a 90-day plan in 3 bullets.
5. RECOMMENDATION - one paragraph, plus the signal that would change it.
Rules: no preamble. Treat inbound interest as a weak signal until someone has a budget. Do not invent deal sizes.
How to use it
Include the real asks from each larger prospect - vague interest gives a vague answer. It cannot judge your sales team's enterprise experience for you.
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