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“Frederic (my co-founder) and I personally sold them. Really it was looking then in the eye and getting them to trust us that it would work and be valuable. It was hard. A real grind in the beginning.”

— Todd McKinnon, CEO and co-founder of Okta

Once you’ve found your early users, how do you get them to pay? I’m dedicating this post to the strategies that today’s fastest-growing B2B businesses relied on to sell their first handful of customers. It turns out there are just three strategies early-on:

  1. Bottom-up + self-service: Users discover your product, sign up for a free plan, love it, and upgrade themselves in order to get more functionality.
  2. Bottom-up + inside sales: Users discover your product, sign up for a free plan, and then are either encouraged by a sales rep (or pro-actively reach out) to upgrade for more functionality.
  3. Outbound sales: Founders or early sales hires reach out to leads, help them trial the product, and then sign them up for a paid plan.

Here’s how the companies I looked at map to these three strategies:

  1. 100% of companies ended up building a sales team, including every bottom-up driven business
  2. Founder-led sales is how most companies kick-started growth
  3. You don’t need to launch with a paid plan if you are going bottom-up. Seven of the twenty-five companies I looked at (including Segment, Figma, and Airtable) had no paid plans when they launched. They then worked with their power-users to figure out what the paid plans should be.
  4. You can adjust your sales strategy down the road — Zoom and Amplitude started sales-driven and later became bottom-up-driven. Box and New Relic did the reverse.
  5. Nearly company offered a free plan from the outset — usually a freemium tier, and occasionally a trial period.
  6. There are four options for charging B2B users: a flat monthly fee, a per-seat monthly fee, a usage-based fee, or a transaction fee. Most of the companies I looked at charge a monthly per-seat fee, and sometimes include multiple changes (per-seat + flat monthly fee, or usage-based + flat monthly fee).
  7. Sales-driven companies love blue logos

Let’s dive in!