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

Guest: Kate Ahlering, CRO of Calendly 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 she wish she was spending more time on? (48:14)