SaaStr 721: How Revenue Leaders at Box, Calendly, and Lattice Scaled From $0 to $100M+ and Beyond
SaaStr 721: How Revenue Leaders at Box, Calendly, and Lattice Scaled From $0 to $100M+ and Beyond
Mark Roberge, SaaStr fan-favorite and Co-Founder and Managing Director of Stage 2 Capital brought together some of the top CROs in SaaS during the SaaStr Annual to share some of their greatest learnings and pivotal moments leading some of the Cloud 100 SaaS companies.
Dini Mehta, former CRO at Lattice, Kate Ahlering, CRO at Calendly, and Mark Wayland, CRO at Box, share their stories and offer advice to founders on:
How do you define and refine an ICP?
Can you start and stop a PLG motion?
What should you look for in an Enterprise rep vs. a Mid-Market rep?
How do you diagnose and solve churn?
How should you handle presenting challenges to your C-suite team when you've just joined the company?
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SaaStr hosts the largest SaaS community events on the planet.
Join us in 2024 at:
SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20
SaaStr Europa: June 5-6 in London. We'll be hosting the 5th SaaStr Europa in London for two days of content and networking. Join 3,000 SaaS and Cloud leaders. Podcast listeners can grab a discount on Europa tickets here: https://www.saastreuropa2024.com/buy-tickets?promo=fave200
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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 KateLinkedIn
The profile of Kate as a UVA basketball captain
Connect with JoubinTwitter
LinkedIn
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins
This episode was edited by Eric Johnson from LightningPod.fm