S5E5: Early Stage, Go-To-Market Strategies with Ash Rust of Sterling Road

In The Room with Ash Rust, Managing Partner at Sterling Road.

Since moving to Silicon Valley in 2008, Ash Rust has become an experienced mentor to startup founders and funders. Ash realized that he didn't like the traditional Silicon Valley approach of meeting someone for a small amount of time before making a decision on a large check, as fast as possible, because “that's the cool thing to do.” Instead, he chooses to spend a lot of time with founders early on to build an organic and more valuable relationship. This allows a better perspective on how Ash can properly assist the project. 

This episode includes insights on making an enterprise sale as an early or first-time founder, the right time to implement a sales team and who should be on it, and the current and future impacts of developing technologies on enterprise sales.

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3:57 - What interested Ash about becoming a founder and sales coach?
7:48 - What is important when making your first enterprise sale?
11:38 - When is the right time to bring a dedicated sales person to your team?
13:41 - How do you balance asking for a sale while managing an overcritical internal mindset?
17:00 - How has the landscape changed over time for making a sale?
18:44 - As technology continues to develop, what will the future of optimizing the sales funnel look like?
21:36 - What are some indicators or metrics of sales success?
24:51 - Are there any overlooked tips in mastering enterprise sales?
26:04 - Who is a woman in Ash’s life that had a profound impact on him and his career?

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Season 5 of The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.

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