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?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch31 Aug 2022

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?

Episoder(1386)

20 VC 002: How to become a VC with Kris Jones

20 VC 002: How to become a VC with Kris Jones

In this session of The Twenty Minute VC, I'm so excited to have the opportunity to interview Kris Jones. Kris has enjoyed an amazing career in the technology industry, founding PepperJam, an internet marketing agency in 1999 and later selling it to Ebay in April of 2010. More recently, Kris has made his transition into the Venture Capital Industry through the founding of an early stage technology investment fund, KBJ Capital, which includes portfolio companies Highlighter.com, French Girls App, ReferLocal.com, LSEO.com and many more incredible companies. In this session you'll learn: Why Kris decided to make the transition from the Startup ecosystem to the world of Venture Capital. How did it feel for Kris, selling his company to Ebay? What was the most important lesson Kris learnt in the journey from having the idea for PepperJam to being acquired by Ebay? What is the key characteristic a Founder must have? What can an individual do to get employed in the Venture Capital industry. Kris is also a prolific writer here are some of his articles, you can check out! Forbes: 15 Steps to Set Your Company Up for a Successful M&A Mashable: 9 Ways Social Media Marketing Will Change in 2014 Citibank: How to Impress a Potential Investor

13 Jan 201522min

20 VC 001: Guy Kawasaki of Apple, Motorola and AllTop.com

20 VC 001: Guy Kawasaki of Apple, Motorola and AllTop.com

Welcome to the 1st episode of The Twenty Minute VC, on today's show we have Guy Kawasaki, Guy is the Founding Partner of Garage Technology Ventures, a seed & early stage venture capital fund investing in extraordinary entrepreneurs with unique technologies. Previously, he was Chief Evangelist of Apple Inc and an advisor to the Motorala Business Unit of Google. Guy is also the author of many best selling books including the recent best seller, The Art of Social Media: Power Tips for Power Users. In this episode we delve into: Why Guy made the transition into the VC industry? What is the most important aspect for a startup to have? What drives Guy insane about startup founders today? What books Guy gives to aspiring entrepreneurs? What software & apps Guy cannot live without? We then finish on a quick fire round where we discover Guy's thoughts on the future of Amazon, Tesla and whether we really are in the midst of a tech bubble. All of the products mentioned in todays show can be found at www.thetwentyminutevc.com If you love the show, please do leave a review on the iTunes store and don't forget to subscribe!

13 Jan 201519min

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