Spent 6 weeks in an enterprise security review. We failed because we didn't have SSO.

Last month, we finally got a demo with a massive prospect—a 500-person company that was exactly our target audience. The demo went perfectly. The VP of Product loved our tool, and the team was ready to sign a $1,500/month contract.

Then, the deal moved to their IT and Security department.

For six weeks, I answered endless questionnaires, filled out vendor risk assessments, and had calls with their security team. I felt like we were making progress. But last Friday, I got the rejection email. The reason? We didn't support SAML-based Single Sign-On (SSO).

I knew SSO was a common enterprise requirement, but I didn't realize it would be an absolute dealbreaker. Because we didn't have it, their IT team refused to approve the purchase. We lost the $18k annual contract over a feature that takes a few days to build.

I feel incredibly naive. I was so focused on building the core product features that our actual users wanted, I completely ignored the "boring" enterprise infrastructure features that the buyers require. Now I have to go back to my team and tell them we need to pause our roadmap to build SSO, just so we can even be considered by these bigger companies.

For those who have moved upmarket: What other "boring" features were absolute dealbreakers for your enterprise clients?

Was it SSO, SOC 2 compliance, audit logs, or custom data retention policies? I need to figure out what else is going to blindside us before we waste another six weeks in a sales cycle