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January 23, 2025

Start with Mid-Market Sales, Not Enterprise

Start with Mid-Market Sales, Not Enterprise

Lots of founders want their first sales to be with large, Enterprise companies like Google or Uber. This is usually quite tough, and it’s often a lot easier to begin with the mid-market and then move up to Enterprise sales. Here’s why:

1. Compliance

Even if a large company really wants your product, they will likely have some significant compliance requirements that are often very hard for a small startup to fulfill. Mid market customers can usually work around these issues.

2. Time to Close

Mid-market customers can pay real money and close in a matter of weeks, sometimes days. Even excited enterprise customers will have to contend with their internal bureaucracy so you can’t expect less than 60 days.

3. Minimal Strategy Changes

If you start with small businesses, their needs are very different from enterprise customers, and you will be pulled to serving smaller company requests. However, mid-market customer needs aren’t usually so different from the enterprise, so helping them won’t distract you from your future, larger customers.

Best of luck out there.

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Ash Rust

Ash Rust

Managing Partner, Sterling Road
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