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?

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?