Enterprise Sales Podcast with The Room

Ash Rust
2 min readFeb 15, 2022


Today my interview with The Room Podcast went live.

We focused on how startups close their 1st Enterprise sale.
Episode link: Apple, Spotify.

1st — VALIDATE THE PROBLEM — Get feedback from potential customers, min 10.

Ask for advice not for them to buy. Need to know if this problem is urgent. If so, it’s easier to get a yes.

Here’s a post with an example cold outreach email.

2nd — DEPLOYMENT — Getting from verbal yes to an Enterprise being live & using your product is a journey.

You will have to go through security, IT & legal reviews in most cases.

Once live, we have to ensure the features we deployed are working. Expect your app to break a lot.

3rd — ENGAGEMENT — We need the customer to be using the product regularly, to ultimately be reliant on it.

Talk to your customers often to find the blockers they’re encountering & motivate them to try again.

Once a customer is reliant, the leverage for pricing switches to you

4th — SIGNED CONTRACT — If a customer needs your product, you can use the threat of them being turned off to ensure your contract is signed & paid on time.

Always try to get an annual contract, paid upfront. Quarterly is a fair compromise.

Plus, plenty more on metrics for success, sales mentality and pricing.

Take a listen and let me know your thoughts….



Ash Rust

Pre-seed B2B Investor in 🇺🇸 🇨🇦 🇬🇧. Email: ash@sterlingroad.com. More info: http://SterlingRoad.com/process