Do not sell to enterprise

In the early days of your startup, you fantasize about becoming big and selling fat contracts to enterprise within a few weeks months years. Trying to close enterprise contracts too early is generally a mistake for the following reasons:

• the sales cycle for an enterprise contract takes months. By the time you expect to close, you may already be dead.

• enterprise contracts require many approvers. A single “no” is often a final “no”. Nobody got fired for buying the established tool in your domain ; nobody want to take the risk of betting on an unknown startup if there is any doubt.

• enterprise contract requires custom development that will take resources away from developing your core product (which is your core asset).

• relying on a few enterprise contracts puts your future at risk. If 80+% of your ARR relies on in a few enterprise contracts, a single customer who churns means large impact on your revenue and may flip you from default alive to default dead.

Instead, focus first on small and medium-size companies:

• you sign the same day (or a few days) after you give them a demo. Money is directly correlated with your product improvements and your ARR grows fast.

• lower friction with one approver at most (CEO or CTO/VP)

• no specific development so that you focus on your core product and differentiation

• if your revenue is made is many small companies, a few companies who churn do not impact your revenue significantly

Focus first on your product and make sure you have a good differentiator. Keep communicating with your customers and keep iterating until you have product-market fit and your sales continuously grow.

Start to consider enterprise sales only when you know you have a strong product-market fit.

Finally, all these sales must be led by you (the founder). Hire a sales team only when you have a repeatable sales process (e.g., how to get a lead and drive them to close). Never before.