Why Every CSM Needs Commercial Skills in the Next 18 Months ft. Jon Johnson (Gainsight)

Customer success is changing fast, and the CSMs who thrive will be the ones who speak the language of revenue. In this episode of Unchurned, Josh Schachter sits down in New York with Jon Johnson, former co-host of [Un]churned & Strategic Principal Customer Success Manager at Gainsight, who manages some of the largest global accounts in the industry. Jon shares how he keeps multinational stakeholders aligned, why empathy still matters at the executive level, and why he thinks CSMs need to take ownership of commercial outcomes before the job forces the issue. They also debate whether SaaS will go “headless” in the next 18 months and how AI has changed Jon’s workload and anxiety. The conversation ends with Jon reading from his poetry collection Caterwaul and a lightning round.

Timestamps

0:00 - Jon Johnson returns to [Un]churned & the banter

3:10 - What Jon does at Gainsight

5:28 - Practising empathy and making customers feel valued

9:53 - Josh makes a surprise announcement

10:41 - 15 years in CS: from startups to global enterprise

11:50 - How customer success changes when you're managing thousands of users 13:10 - Why CSMs are moving closer to the executive level

17:20 - The three pillars: commercial, strategic, technical

19:38 - Why CSMs need commercial accountability

24:15 - Will B2B SaaS become headless in the next 18 months?

28:10 - AI, anxiety, and staying proactive

32:32 - Caterwaul: turning anxiety into art

35:18 - Jon reads “Holy Hands”

37:00 - Deconstructing faith and holiness

39:10 - Lightning round

What You'll Learn

- How AI is pushing CSMs toward more strategic, executive-level work

- Why being proactive about AI reduces AI anxiety

- Why CSMs should build commercial skills now, before they’re forced to

- How to reframe “value” so CSMs can tell the story of their impact

- Why enterprise SaaS adoption will move differently from SMB and mid-market

- How consumption and outcome-based pricing can give CS a real seat at the table

- Whether SaaS will really go headless, and what that means for CS teams

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Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com

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Where to Find the Guest

Jon Johnson: https://www.linkedin.com/in/jonwilliamjohnson/

Jon's Music - Wild Coast: https://open.spotify.com/artist/17TwPEUjOWx4BESKVsqrPK?si=8DjlJdq0SWePHS5r-v1FGQ

Jon on Substack: https://jonwilliamjohnson.com/

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Where to Find the Hosts:

Josh's LinkedIn: https://www.linkedin.com/in/jschachter/

Unchurned Substack: https://unchurned.substack.com/