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Crossing the Enterprise Chasm

What is good for the Developer IS good for Enterprise

Notes from a conversation on moving upmarket without losing the thing that made the product good in the first place.

1 January 2026

This episode is part of Crossing the Enterprise Chasm, our series on what changes when a developer product starts selling to companies.

The through-line is the same one we keep running into while building Paycux: the requirements that arrive with an enterprise deal are not arbitrary, and the teams who treat them as specifications rather than obstacles move faster than the ones who argue with them.

Below are the points worth keeping if you are somewhere in the middle of the same transition.

Takeaways

  • Developer trust is spent, not earned back. Every pricing and packaging change draws on the same balance.
  • The first enterprise deal reshapes the roadmap more than the revenue justifies — plan for that, rather than being surprised by it.
  • Self-serve and sales-led are not stages; run both and let the customer pick the path.

The features every one of these conversations ends up describing

SSO, provisioning, roles and audit logs — already built, behind one API.