This week I had the huge pleasure of chatting with one of my subscribers, Kit Wetzler, VP of Sales at data observability platform Bigeye about what he’s learned from being the first sales leader at early stage startups.

Coming in as the first sales leader is always tricky, as you have to take over sales duties from the founder and transition away from a value prop based on the founder’s personality to one based on business value. Kit is an absolute goldmine of insight on how to do this successfully.

From how to figure out if a founder is a good fit to work for, to what needs to change when taking over from a founder-led sales motion, to defining sales processes that keep deals moving forward, to using mutual action plans to get through complex POCs, to hiring the right profile of account executive, to coming up with a plan that’s achievable, to partnering with product to sell and deliver on the future roadmap, Kit has done it all and explains it really well.

Its a must-listen for anyone looking to jump into a sales leadership role at an early stage startup, as well as a handy refresher for anyone who is currently in the role. I personally learned a lot from speaking with Kit!

Give it a listen here or on Apple Podcasts and let me know what you think! And if you haven’t done so already, please consider subscribing.

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Podcast Contents

0:25 — Tell us about Bigeye and the problem you’re solving
1:00 — You came up through big companies like Citrix and Amazon. How did you transition into early stage sales leadership?
1:55 — What lessons have you learned from taking over from the founder as head of sales?
3:30 — Which processes do you build first?
7:15 — How do you structure a proof-of-concept (POC)?
9:05 — How do you stop POCs from going sideways?
12:10 — How do you keep stakeholders engaged during a POC?
13:35 — How do you prospect technical buyers at an early stage company?
18:20 — What does the initial team typically look like and how do you grow it?
21:35 — What should founders look for in their first sales leader?
24:15 — What are the biggest things first sales leaders get wrong?
26:00 — How do you figure out if a founder is a good fit for you?
28:10 — What advice would you give on coming up with a plan that’s achieveable?

Additional reading

The Revenue Architect

How to be the first sales leader at a tech…