Understand the slog of early Enterprise GTM.
We know the lore of 8 figure enterprise deals that stack to make a Unicorn (mid market predictability helps too). But fewer live to tell about the slog that is early enterprise sales. Here are a few reasons why your tiny team is on a Mission Impossible.
The sales cycles are painfully long. Especially if you start in innovation, especially if it’s a vague, stretch use case POC (even paid ones rarely keep you out of the red).
Customer ask for custom features all the time. They mean well, they gather asks from the whole village and look at you with puppy eyes. These tend to delay your product roadmap and bug down your eng team in dead end projects. Think about integrations into legacy custom systems.
Expectations constantly change. If you are working with innovation, those teams are often knew and untested. They have limited clout and are expected to change giant orgs from within. The operationalizing teams (who scale successful POCs) often have very different requirements that will delay a larger deployment or cost a fortune to set up before signing the large contract.
If it’s deep tech (computer vision, machine learning), the performance of your product isn’t guaranteed and often dependent on things outside of your control (customer data, consistent problem definition across data, etc.). Sometimes additional hardware setup is required which nobody at the client or your startup knows about.
You will feel like giving up 100 times. Just remember that it’s still a lot easier to up sell an existing account (after proving your value and building trust) than to break into a new one. There are many lessons to be learned in the trenches that immediately translate into marketing and a play book for your next client.
Finally, when enterprises buy, they buy a lot and they stick around. Once you get the first Insurance logo, the rest will follow at 1/2 the sales cycle and cost.