The 60 Second Podcast

Jessica Gilmartin, CMO and CRO of Calendly

• Matt McCoy

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In this punchy episode of the 60 Second Podcast, we sit down with the former Chief Revenue & Marketing Officer at Calendly, who’s also a Board Member at TextExpander and Limited Partner at Stage 2 Capital. With deep experience leading go-to-market teams, they share the one question every founder should be asking when hiring their first marketing leader — and the common mistake that sets startups back.

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Q: What's a question you wish more founders asked you?

I actually get asked this question a lot by founders. And the number one question I wish founders would ask me is:

“What is the type of CMO that I should hire for the next two years?”

Every founder I talk to wants to hire someone who has seen scale. So if they're at $5 million in revenue, they want to hire someone that has seen $50 million or $100 million.

That’s a big mistake.

Those bigger company CMOs don’t want to get into the tactics as much as the startup CMOs do. If you're at $5 million in revenue, you need someone that can be really tactical — someone who knows how to hire that first person, how to manage small teams, and how to be scrappy.

It doesn't matter if they can manage a team of 30… because you probably won’t have a team of 30 in the next two years.

So my absolute number one piece of advice for founders:
 When you're looking for that first CMO, don't worry about the person who can 10x or 20x you.

Worry about the person who can 2x or 3x you over the next two years.