197. Rav Dhaliwal, Investor and Limited Partner, Crane - CS Meets Revenue: AI, Agents, and the New Customer Success

197. Rav Dhaliwal, Investor and Limited Partner, Crane - CS Meets Revenue: AI, Agents, and the New Customer Success

In this episode, we’re joined by Rav Dhaliwal, recovering software exec turned early-stage VC at Crane. A longtime CS leader and board-level advisor, Rav breaks down how AI is reshaping Customer Success, from onboarding and telemetry-driven predictions to agentic workflows, while pushing CS to converge with account management and get far more revenue-centric.

We spoke with Rav about what AI should (and shouldn’t) automate, how to keep relationships authentic, and how leaders actually drive adoption, treating AI not as a tool drop but a behavioral change program.

Here are some of the key questions we address:

  • Will AI compress or redefine CS, and where does it create leverage vs. require human expertise?

  • What does the CS–Account Management convergence look like in practice (discovery, multi-threading, commercial acumen)?

  • Which AI use cases move the needle now: telemetry-based churn/upsell prediction, voice sentiment, and agentic next-best-action?

  • How do you avoid the “AI for efficiency only” trap and tie it to revenue, cost, and risk outcomes that customers actually buy?

  • What’s the playbook for AI adoption in GTM/CS? How do leaders run a change program (not a tool rollout) and measure progress?

  • Where are the authenticity risks and how do you keep the customer relationship human?

  • How far can we push AI-led onboarding and what’s the 90% automated vs. 10% bespoke split likely to be?

🎧 Tune in to hear Rav’s pragmatic take on CS in the age of AI: more signal, smarter workflows, tighter revenue alignment and leadership that treats AI as an operating change, not a shiny tool. Also, watch out for his new book coming out shortly on Founder-Led Sales!

Jaksot(211)

139. Helena Tivell, VP of People, Kognity -  Leadership development - how to develop your  leaders!

139. Helena Tivell, VP of People, Kognity - Leadership development - how to develop your leaders!

In this episode, we speak with Helena Tivell, VP of People, Kognity, the all-in-one digital teaching and learning platform - with interactive content, analytics, and assessment support. We talked with...

30 Huhti 202447min

138. Daan Assen, Founder, SwipeGuide  - How do you succeed with your customer pilot projects?

138. Daan Assen, Founder, SwipeGuide - How do you succeed with your customer pilot projects?

In this episode, we speak with Daan Assen, Founder, SwipeGuide, the platform that empowers frontline teams to connect knowledge, collaboratively solve problems, and continuously improve processes to e...

24 Huhti 202451min

137. Bas van Wijk, VP Commercial Operations, AskCody  - Getting the inbound engine off the ground!

137. Bas van Wijk, VP Commercial Operations, AskCody - Getting the inbound engine off the ground!

In this episode, we speak with Bas van Wijk, VP Commercial Operations, AskCody, the Meeting Management Platform for Microsoft that's driving meeting efficiency through an intelligent Meeting Managemen...

13 Huhti 202448min

136. Ingrid Bonde Åkerlind, Principal, Oxx - You have Product-Market-Fit, now what?

136. Ingrid Bonde Åkerlind, Principal, Oxx - You have Product-Market-Fit, now what?

In this episode, we speak with Ingrid Bonde Akerlind, Principal, Oxx, a specialist SaaS investor, who provides each entrepreneur with a support system of unique specialist expertise and network, and a...

11 Huhti 202459min

135. Markus Ståhlberg, CEO & Co-Founder, N.Rich - Outplay when you can't Outspend!

135. Markus Ståhlberg, CEO & Co-Founder, N.Rich - Outplay when you can't Outspend!

In this episode, we speak with Markus Ståhlberg, CEO & Co-Founder, N.Rich, the Account-based GTM Platform best suited for fast-growing mid-market and enterprise companies. It's been recognized in the ...

8 Huhti 202455min

134. Vincent Jong, VP Product, Dealfront - PLG and Human approach in symbiosis!

134. Vincent Jong, VP Product, Dealfront - PLG and Human approach in symbiosis!

In this episode, we speak with Vincent Jong, VP Product, Dealfront, the Go-to-Market Platform giving sales and marketing teams the data, applications, and insights they need to win any European market...

3 Huhti 202455min

133. Janus Klok Matthesen, Co-founder and CTO, Pixelz - Is AI going to replace Software Engineers?

133. Janus Klok Matthesen, Co-founder and CTO, Pixelz - Is AI going to replace Software Engineers?

In this episode, we speak with Janus Klok Matthesen, Co-founder and CTO, Pixelz, the post-production software for global brands, retailers, and photo studios, having retouched more than 55 million pro...

26 Maalis 202459min

132. Martin Lidgard, Founder & CEO, Web Manuals - Design your future with strategic projects!

132. Martin Lidgard, Founder & CEO, Web Manuals - Design your future with strategic projects!

Martin Lidgard, Founder & CEO, Web Manuals, the All-in-One Document Management System For Aviation Professionals that has bootstrapped past 10m Euro in ARR and continues to grow fast globally. We talk...

20 Maalis 20241h 1min

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