CRO Calendly, Kate Ahlering: Embracing Leadership - On and Off the Basketball Court

Kate Ahlering might be the perfect guest for this podcast. She eventually worked her way up to Chief Sales Officer of Glassdoor, but when she joined in 2013, she helped define the company’s leadership framework as GRIT: Growth, Results, Integrity, and Team. Glassdoor has continued using those values since her departure in 2020, and now as the CRO of Calendly, she is applying a similar framework to another fast-growing enterprise.

In this episode, Kate and Joubin discuss her first leadership experience, captaining her college basketball team before ever playing a game; the wild ride of working at Glassdoor when it was doubling every year; the perspective and confidence that comes from working experience; brokering consensus when deciding a company’s values; the increasingly complex use cases for Calendly; and a ridiculous Twitter feud over “Calendly etiquette.”

In this episode, we cover:

• Kate and Joubin’s past interactions, including a disagreement over San Diego cuisine (03:02)
• How being raised by two salespeople and playing basketball at the University of Virginia shaped Kate’s worldview (06:01)
• Working at Glassdoor “never felt easy,” but she later realized it was a once-in-a-lifetime experience (14:47)
• Her big legacy at Glassdoor, defining its values as GRIT: Growth, Results, Integrity, and Team (20:38)
• Building trust with a team in a rapidly-changing environment, and working alongside Indeed — a former competitor now owned by Glassdoor’s parent company (26:16)
• Calendly’s interview process and the dangers of offering a thorough plan before you’re inside the company (32:08)
• The surprising depths of Calendly’s complexity in enterprise, and why founder Tope Awotona (accidentally) made the business model freemium (36:15)
• Kate could have gone almost anywhere after Glassdoor — why she chose Calendly, and what motivated her to achieve? (42:36)
• When she’s going to bed every night, what does Kate wish she was spending more time on? (48:14)

Links:

• Connect with Kate
  • LinkedIn
  • The profile of Kate as a UVA basketball captain
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: grit@kleinerperkins.com
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm