20Product: Calendly CPO Annie Pearl on Why All PLG Companies Eventually Need to Embrace Enterprise, Why it is Easier to Scale into Enterprise than Visa Versa and the Calendly PLG Playbook; What Works and What Does Not?

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4.4 • 637 Ratings

🗓️ 31 August 2022

⏱️ 45 minutes

🔗️ Recording | iTunes | RSS

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Summary

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. The company now has over 10M users around the world and over 50,000 companies loving the product. As for Annie, before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70 person product and design org. Prior to Glassdoor, Annie led enterprise product teams at Box both before and after their 2015 IPO. If this was not enough, Annie is also on the Board of WorkRamp and Well Health.

In Today's Episode with Annie Pearl We Discuss:

1.) Entry into Product From Consulting:

How did Annie make her way into the world of product and come to lead product teams at Box and GlassDoor?
What are 1-2 of her biggest takeaways from her time at Box and GlassDoor? How did they impact her product mindset?
What does Annie know now that she wishes she had known when she started in product?

2.) PLG vs Enterprise: What, When, How:

Is it possible to do PLG and top-down enterprise strategy together from Day 1?
Why does every PLG company eventually have to adopt an enterprise strategy?
What are the single biggest challenges companies face when moving to enterprise?
How do founders know when is the right time to make this transition?
How do founders need to restructure their org to make the transition to enterprise?

3.) Building the Product Bench: Hiring:

When is the right time to hire your first product leader? What are the core signals?
What are the core character traits needed for a first product leader?
How do we specifically structure the interview to test for them?
Who do we bring into the interview process from other parts of the org?
Do we do case studies with candidates? If so, how long do they have with the data? What is the difference between good vs great with case studies?

4.) Product Strategy, Reviews and Alignment:

How does Annie assess how often product strategy should be reviewed? When should it change?
How does Annie approach post-mortems? What is the right way to structure them?
How does Annie create alignment between sales and product? Why is this so important?
What is the single biggest product mistake Annie has made? What did she learn?

Transcript

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0:00.0	Welcome back to another very special 20 product episode. This is the monthly episode where we sit down with one of the leading product minds to discuss scaling both product and product teams, sharing their tips, tactics and experiences. And today I'm super excited to welcome Annie Pearl, CPO at Callanley, the company that makes scheduling meetings simple and painless. The company now has over 10 million users around the world
0:21.5	and over 50,000 companies loving the product. As for Annie, before Callanley, she led Glassdoor's
0:27.0	product vision and user experience managing a 70-person product and design org. And prior to Glassdoor,
0:32.9	Annie led enterprise product teams at Box, both before and after their 2015 IPO. And if this wasn't enough,
0:39.2	and he's also on the board of WorkRamp and WellHealth. And a huge thank you to Ted Blosser at
0:43.9	WorkRamp, Topi, Callanley's CEO, and Adam Draper for some amazing question suggestions today. Really did
0:49.8	make such a difference. But before you dive into the show today, you have to check out Builder Dot AI. They make building software so easy that anyone can do it. If you have a vision,
0:59.0	you can build it with builder.a.i. And one of my favorite products of theirs is Studio Rapid.
1:03.9	I always think the number one reason people fail is they don't start. And Studio Rapid is the
1:08.8	perfect tool for when you need an MVP fast. And when I say fast,
1:12.9	you can build simple, beautiful native apps in less than one day. But don't just take my word
1:17.8	for it. Take the words of BBC, Pepsi, Fujitsu, some of the world's leading brands, all loving
1:23.8	and using the builder.a.i product suite. Head over to builder.a.ai to find out more.
1:29.1	And speaking of creating beautiful customer experiences and products, if your business runs on a
1:33.3	mobile app, you have to check out UXCAM. Designed specifically for mobile product teams.
1:38.7	UXCAM helps build better apps by making user motivations and frustrations loud and clear.
1:44.1	Product teams love this app experience analytics platform that empowers them with clarity and speed.
1:49.1	UXCAM auto captures billions of micro-interaction level data like screen swipes and taps,
1:54.6	with tools like session replay, heat maps, funnels, crash analytics and auto-capture of user
2:00.1	frustrations and bugs, it has never
2:01.8	been easier to uncover real user behavior, join over 30,000 apps such as Costa Coffee, Nando's,
2:08.0	delivery hero and Rappi, who optimise their product with UXC. If you're not using UXC,
	...

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