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Lenny's Podcast / episode intelligence

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

26 Feb 2023 23 published claims 2 attributable people

Speakers in the public record

Claim mix

belief 13evaluation 4recommendation 3preference 2commitment 1

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Every row below preserves an exact excerpt. Identified speakers are linked; unresolved voices are labeled and excluded from people counts.

Claim ledger

The useful parts, with receipts.

23 published records

01 / belief

You'll need to drive growth very actively in these new ways that you're describing. And I think people don't often realize that they just wanted to find something that was viral and then things are going to go great, but it tapers off.

“You'll need to drive growth very actively in these new ways that you're describing. And I think people don't often realize that they just wanted to find something that was viral and then things are going to go great, but it tapers off.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

02 / belief

When teams come in to present as part of our product reviews, we have a template that keeps reinforcing who's the target customer, who's the target user within that customer base, what are their needs and then how are we going to solve their needs better than any alternative that there is on the market. So, I think there's lots of different reinforcing mechanisms to that focus.

“When teams come in to present as part of our product reviews, we have a template that keeps reinforcing who's the target customer, who's the target user within that customer base, what are their needs and then how are we going to solve their needs better than any alternative that there is on the market. So, I think there's lots of different reinforcing mechanisms to that focus.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

06 / belief

Are we going to be really trying to promote this? So, I think there's a lot of ancillary activities around the actual program itself that have to be taken into consideration to make sure that it is actually very successful.

“Are we going to be really trying to promote this? So, I think there's a lot of ancillary activities around the actual program itself that have to be taken into consideration to make sure that it is actually very successful.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

07 / belief

I think another "more formal" way to get into PM is really by just directly applying to a junior PM role where there's no expectation of any sort of experience.

“I think another "more formal" way to get into PM is really by just directly applying to a junior PM role where there's no expectation of any sort of experience.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

08 / belief

The rest of the interview, they're trying to tell you all the wonderful things they did and all the accomplishments they had. And so, I think the rawer the answer in terms of how bad it was and why, the better.

“The rest of the interview, they're trying to tell you all the wonderful things they did and all the accomplishments they had. And so, I think the rawer the answer in terms of how bad it was and why, the better.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

10 / belief

I think at the end of the day, the real benefit of the structure is really to say at the end, we want to be thinking about everything we're doing through the lens of the end-to-end user experience.

“I think at the end of the day, the real benefit of the structure is really to say at the end, we want to be thinking about everything we're doing through the lens of the end-to-end user experience.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

11 / belief

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 when I joined again about two years ago, and I think we're around 60 this year.

“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 when I joined again about two years ago, and I think we're around 60 this year.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

13 / belief

Since then, we've grown the group to about 23 heads of products and CPOs and expanded the charter a bit, which I think is interesting to help product leaders not just be successful in their current role, but also how to think about setting them up for success in the role after this.

“Since then, we've grown the group to about 23 heads of products and CPOs and expanded the charter a bit, which I think is interesting to help product leaders not just be successful in their current role, but also how to think about setting them up for success in the role after this.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

14 / preference

How do you use data and AB testing to make decisions? So, I think that kind of consumer mentality and how you approach product, I then have brought with me to Calendly, which is really a blend of both, right?

“How do you use data and AB testing to make decisions? So, I think that kind of consumer mentality and how you approach product, I then have brought with me to Calendly, which is really a blend of both, right?”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

15 / evaluation

I imagine when people look at a CPO, they imagine they just know everything already. They have a bunch of friends in the same role, but I think in reality, it's a lonely role a lot of times.

“I imagine when people look at a CPO, they imagine they just know everything already. They have a bunch of friends in the same role, but I think in reality, it's a lonely role a lot of times.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

17 / preference

When I was at Box, I was a product manager on the enterprise team and I spent a ton of time in the field and I don't know how I would possibly know how to have what to have built or how to build it to solve the needs of our customers if I didn't have that close relationship with the sales team and be able to lean on them because they're talking to, 10X of them were customers that I was able to ever talk to within any given week, really lean on them to be the voice of the customer to help me make the best product decisions that I could.

“When I was at Box, I was a product manager on the enterprise team and I spent a ton of time in the field and I don't know how I would possibly know how to have what to have built or how to build it to solve the needs of our customers if I didn't have that close relationship with the sales team and be able to lean on them because they're talking to, 10X of them were customers that I was able to ever talk to within any given week, really lean on them to be the voice of the customer to help me make the best product decisions that I could.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

20 / recommendation

You wouldn't necessarily want to bring on a bunch of sales folks who are at Oracle who are heavy in selling into CIOs in the early days because that's just not who you're the buyer's going to be.

“You wouldn't necessarily want to bring on a bunch of sales folks who are at Oracle who are heavy in selling into CIOs in the early days because that's just not who you're the buyer's going to be.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

21 / commitment

This starts again, I sound like a broken record, but with this really clear strategy around where we're going over the next couple of years and then we take that and we break that down into what are the most important things we need to do as a company this year in order to be able to make the right progress against that strategy.

“This starts again, I sound like a broken record, but with this really clear strategy around where we're going over the next couple of years and then we take that and we break that down into what are the most important things we need to do as a company this year in order to be able to make the right progress against that strategy.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast

22 / evaluation

I think the first is, when you're making that transition from PLG to adding in the sales led motion, because you're starting from PLG, it's tends to be much more inbound in nature.

“I think the first is, when you're making that transition from PLG to adding in the sales led motion, because you're starting from PLG, it's tends to be much more inbound in nature.”
Speaker
Annie Pearl
Publisher
Lenny's Podcast
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