Chris Grouchy

The piece of b2b startup advice I find myself giving over and over again recently is figure out how your product can make a *significant* difference in the success of your customer’s business - whether that is driving significant revenue, huge improvements in their customer retention, massively lowering their cac, cutting significant costs, etc. AI has opened this door. Please walk through it.

We just signed a multi-year deal with one of the largest fintech companies in the world ($25B+ revenue). Here's how to approach negotiating multi-year commitments: The biggest lesson I learned — don't be afraid to ask for one. It sounds simple, but it's something no one ever told me. After you get technical sign-off, bring it up in a 1:1 conversation with your internal champion. Ask them if the long-term value is clear (hopefully it is), and then directly ask them how realistic a multi-year commit is. You'll hear 'no' a lot, but sometimes...it just might work. Monthly contracts are great validation, but don’t underestimate the power of pushing for annual or multi-year commitments. If you can get it, it indicates deep commitment from the market. For Extend, it shows we're not just solving a short-term pain point — we're becoming infrastructure that customers depend on for the long haul. But they're not easy to land, especially with F500s. Procurement, security reviews, legal — the complexity ramps up fast. This initial land took longer because we didn't initially have a key stakeholder involved. We weren't afraid to pause the process until we had the right internal advocate on board—and because we did, the likelihood of a successful multi-year rollout increased dramatically. Very cool milestone. We also got logo rights, so keep an eye out for the official announcement soon!