What I learned selling to banks from the vendor side, after years doing it across LatAm (I will not promote)

I spent years on the vendor side of enterprise deals with banks and insurers in Latin America, first as CFO and then as COO of a proptech. Most of what I read here about enterprise sales misses what actually decides these deals. Seven things I wish someone had told me. The cycle is not long because the bank is slow. It is long because you are talking to the wrong person. The one who gets excited about your product usually has no budget and no mandate. Find whoever owns the P&L line your product moves, and accept that reaching them takes three meetings you would rather skip. Compliance and InfoSec kill more deals than pricing does. Ask for the vendor security questionnaire in the second meeting, not after the commercial agreement. That questionnaire is the real sales process. Everything before it is theater. A pilot with no budget line attached is a rejection with better manners. If nobody had to move money internally to run it, nobody has to defend it when it ends. Ask who is funding the pilot. If the answer is vague, you do not have a pilot. Your champion will leave or get reorganized. Assume it from day one and build a second relationship one level above and one seat sideways. Every deal I lost late, I lost this way. Banks do not buy cheap, they buy defensible. Pricing low reads as risk, not value. What the buyer is actually purchasing is a decision that survives an audit and a bad quarter. Do not build custom work for one bank unless they pay for the build. Every one of them asks. The ones that pay are the ones that are serious, and that is the cheapest qualification test you will ever run. Insurers are not banks. Slower to decide, faster to integrate, and far more sensitive to how you handle their data. Do not reuse the same playbook. What I would do differently: I would qualify on procurement reality before product fit. Half the deals I chased were never going to close, and the signal was visible in the first month if I had been willing to ask uncomfortable questions early.