GTM 99: Mastering Customer Success in the AI New Age with Jon Dick

Jon Dick is the Global SVP of Customer Success at HubSpot where he’s focused on helping millions of organizations grow better. Prior to customer success, Jon led marketing teams at HubSpot, Trunk Club, and Klout. He has a background in improvised comedy and earned his MBA from the Harvard Business School.

Discussed in this Episode:

  • The rising importance of customer success in the age of AI and efficiency.
  • Balancing proactive and reactive strategies to serve 200,000+ customers.
  • The evolution of content marketing from “clicks to conversations”.
  • Choosing people over product and finding passion in your work.
  • The power of generalists and the pitfalls of over-specialization in CS.
  • Go-to-market tactics that are working for HubSpot, from chatbots to intent data.


3:22 – John’s experience with improv comedy and how it applies to business.

9:45 – Is an MBA still relevant for today’s fast-changing market?

13:44 – The new age of customer success and rising importance of AI.

18:49 – Balancing proactive and reactive strategies to serve 200,000+ HubSpot customers.

24:25 – The shift from “clicks to conversations” in content marketing.

34:29 – The power of working with people you like and John’s HBS reunion story.

42:09 – Structuring customer success teams for series B companies.

48:15 – One thing revenue leaders believe to be true that Jon thinks is bull$***: obsessing

over lead volume instead of lead value.

50:49 – One thing that is working for Jon in go-to-market right now: leveraging chatbots and intent data to drive conversions.

Guest Speaker Links (Jon Dick):

Host Speaker Links (Scott Barker):


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  • Brought to you by OrumOrum is an AI-powered live conversation platform designed to supercharge sales activity, connect sales teams, and drive more revenue over the phone. Orum’s platform includes an AI-dialer that automates the manual aspects of calling and get sales reps into more conversations, a virtual sales floor for teams to build camaraderie and learn from one another, as well as analytics and coaching tools to help teams improve together.

The GTM Podcast
Features conversations with well-known tech executive, VC, and founders – the expert operators in the trenches who have ‘been there, done that’ to build some of the fastest-growing software companies. Every week, a guest joins Scott Barker to dissect their stories, revealing expert insights around what worked, what didn’t, and how things actually went down.

This podcast is produced by GTMnow, the media brand of VC firm GTMfund – sharing insight on go-to-market from working with hundreds of portfolio companies backed by over 350 of the best go-to-market executives.

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