Spent 5 months on an enterprise deal, only to lose the deal to the CPO's buddy

I have a startup in the AI Agents domain, which is an extremely competitive space with 100s of similar products. However, we differentiate by focusing a bit more on enterprises, data compliance, PII encryption, and serverless / self-hosted setups. Because of this, we generally work closely with a client's tech team rather than their customer support team.

In May, we received an inbound inquiry from a multi-billion dollar company. Our first meeting went great. They loved our product, and we went ahead with multiple demos, signed NDAs etc.

Eventually, they evaluated our compliance. Our ISO 27001 certification was still in progress at the time, so they asked us to wait until it was finished. We worked very hard throughout the month of June and successfully got our certificate, complying with almost 220 items.

We reconnected in mid-July and they started testing. I gave them a lot of options, and we were continuously working on different versions of the product together. We kept this momentum going from July until mid-August.

Suddenly, from mid-August onward, their team's interest seemed to drop off randomly. They stopped responding to our emails and went completely quiet.

Later on, I reached out to a friend who works internally at that organization to see what happened. I found out that their CPO had recommended a different company, so the team migrated to them. Just like that, 5 to 6 months of my effort were wasted.

They haven't even officially informed me yet. My contact told me that because their volume of work is so high, they might have a demand for us in the future and want to keep us around as an option - but for now, they have gone with the CPO's seller.

What did I do wrong while closing this enterprise SaaS client?

2 points | by milanspeaks 1 hour ago

3 comments

  • jqpabc123 2 minutes ago
    You were competing against "crony capitalism".

    You are not alone. This is fairly common in the "enterprise" space.

    I spent years try to court an enterprise company in order to offer them comparable service for half their current cost.

    Eventually, I was told it wasn't going to happen. Why? Because the VP in charge of this was best friends with a VP from their current service provider.

    Bottom line --- competition is for little people. The big people collude with one another.

  • ericmay 1 hour ago
    > What did I do wrong while closing this enterprise SaaS client?

    Well if the work you were doing is necessary for your company and will enable you to sell your product to other companies it’s not really a loss. If anything it was an opportunity to get real feedback and see where your shortcomings are.

    What did you do wrong while closing the enterprise SaaS client?

    Probably that you didn’t close the deal in June (or prior to doing any work at all). Alternatively, nothing at all. Maybe you have a great product but your pricing is bad. Maybe you thought these demos were going well but they weren’t. Any number of things. If you were spending 5-6 months working on a product for this client without a contract - don’t do that.

    The wrong answer is “CPO’s friend”. That’s your ego speaking.

    Maintain close contact, and keep them informed of new product features and ask if you can schedule a demo from time to time for feedback and to see if they like any of the features. Keep a good relationship. Even if it’s with the most junior person on the team. Today’s CPO might not be the future CPO.

  • CodingJeebus 1 hour ago
    Welcome to enterprise, stuff like this happens all the time. There's not a whole lot to be done about losing out to an alternate vendor based on an exec's personal recommendation. I wouldn't frame it as "what did I do wrong?", because there might not have been anything you could do to win that deal. This just happens sometimes.

    The lesson is that relationships matter a ton in any enterprise play. It sucks in hindsight, but it never feels good to invest so much in a big potential client for it not to work out. And upfront spec work is, unfortunately, a common and necessary evil in the enterprise world.

    Sounds like you were decently close to closing a whale, so that's positive. Clearly you have something that somebody wants, so live to fight another day.

    • milanspeaks 1 hour ago
      Thank you for that wonderful last sentence. Super motivating.