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Annie Pearl

CVP & GM, Azure Experiences @ Microsoft

Leads Azure portal, mobile, and Copilot experiences at Microsoft. Former CPO at Calendly.

“Behind the scenes of Calendly’s rapid growth, covering product strategy and execution, team leadership, and product design.”

Career History

CompanyRoleYears
MicrosoftCVP & GM, Azure Experiences & Ecosystems2023-present
CalendlyChief Product Officer~2020-2023
GlassdoorVP of Product~2017-2020
BoxDirector of Product Management~2014-2017

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Episodes (1)

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Quotable Clips

“All right, well I love this question to kick us off. We actually have a whole blog post about this if you're curious to learn more.”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

4:31
“That's good. That's what we like to hear.”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

5:54
“Internal job board apply, when you're in the company.”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

8:45
“And then, another flavor of that is sometimes companies will have these SME programs.”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

8:59
“Subject matter expert. So, you'll say, "Hey, I want to make sure we have subject matter expert in our CS team on this area of the product." And they'll partner really closely with the product manager ...”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

9:05
“Yes. You could just use associate product manager and you'll see all the open jobs out there and then go apply to them.”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

10:45
“And are we doing, is this really an APM program for internal folks? Is this external? Are we going to be really trying to promote this? So, I think there's a lot of ancillary activities around the act...”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

12:49
“Let's see, when I joined about two years ago, I think the company was about 150 people and I think we're about 600 now. And then the product team, there were about 15 product managers and designers wh...”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

13:56
“Product managers, designers, and a research team. Yeah.”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

14:14
“Yeah. So, as I mentioned, we've got product managers, we have designers, we have a research team, and then product operations. And then, on my product leadership team, we have head of design, head of ...”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

14:30
“And then lastly, we have a platform team who's really thinking about how do we embed Calendly into the business processes of the organizations that we support and that we provide our product into. And...”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

18:31
“That's right, that's right. Yeah, trying to sell it to, and then the persona of who's going to be using the functionality. And then, really having those teams hone and own those personas as they're de...”
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Annie Pearl

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

18:54