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!

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Jaksot(214)

214. Daniel Thulfaut, Head of Product at saas.group - Why AI Is Killing Traditional Product Management

214. Daniel Thulfaut, Head of Product at saas.group - Why AI Is Killing Traditional Product Management

In this episode, we sit down with Daniel Thulfaut, Head of Product at saas.group, one of Europe's most active SaaS acquirers. With 24 companies in the portfolio and more than €100M in ARR, Daniel has ...

9 Kesä 59min

213. Artti Aurasmaa, CEO of Staria - Why the CFO Is Becoming the Most Strategic Role in SaaS

213. Artti Aurasmaa, CEO of Staria - Why the CFO Is Becoming the Most Strategic Role in SaaS

In this episode we sit down with Artti Aurasmaa, CEO of Staria, to discuss how the CFO role is evolving from financial reporting to strategic leadership. Artti has spent more than 25 years helping com...

4 Kesä 47min

212. George Storm, CRO at N.rich - Why your SaaS Forecasting Is Broken & Inaccurate

212. George Storm, CRO at N.rich - Why your SaaS Forecasting Is Broken & Inaccurate

In this episode, we’re joined by George Storm, CRO at N.rich, for a conversation about why traditional B2B SaaS forecasting is no longer good enough in today’s market. George shares how N.rich, the Eu...

28 Touko 58min

211. Massimo Arrigoni, CEO of Beefree - The SaaS Apocalypse? Massimo Arrigoni Says No

211. Massimo Arrigoni, CEO of Beefree - The SaaS Apocalypse? Massimo Arrigoni Says No

In this episode, we’re joined by Massimo Arrigoni, CEO of Beefree, the content creation platform behind thousands of SaaS products and one of the companies with a uniquely broad view of what’s actuall...

17 Huhti 56min

210. Jens Levin, Founder & CEO of Sitoo - No Overnight Success: 22 Years of Focus, Teamwork, and Playing the Long Game

210. Jens Levin, Founder & CEO of Sitoo - No Overnight Success: 22 Years of Focus, Teamwork, and Playing the Long Game

In this episode, we’re joined by Jens Levin, Founder & CEO of Sitoo, the retail SaaS platform powering in-store experiences for leading brands across the world. Today, Sitoo has 20M Euro in ARR, 40%+ ...

1 Huhti 50min

209. Elena Verna, Growth at Lovable - How to Grow When Everyone Can Copy Your Product

209. Elena Verna, Growth at Lovable - How to Grow When Everyone Can Copy Your Product

In this episode, we’re joined by Elena Verna, growth expert and currently leading growth at Lovable, one of the fastest-growing companies in tech. Elena shares why the old growth playbooks are breakin...

26 Maalis 1h 2min

208. Lisen Zethraeus, CMO at Stratsys - How to Make Your Experts the Face of Your Brand

208. Lisen Zethraeus, CMO at Stratsys - How to Make Your Experts the Face of Your Brand

In this episode, we’re joined by Lisen Zethraeus, CMO at Stratsys, to talk about how B2B SaaS companies can turn internal expertise into thought leadership that builds trust and creates demand. Strats...

19 Maalis 50min

207. Adam Dorrell, CEO & Co-Founder of CustomerGaige - Founder-Led Sales vs Scaling: The Hard Transition Nobody Talks About

207. Adam Dorrell, CEO & Co-Founder of CustomerGaige - Founder-Led Sales vs Scaling: The Hard Transition Nobody Talks About

In this episode, we’re joined by Adam Dorrell, CEO & Co-Founder of CustomerGaige, for a candid conversation about one of the hardest founder transitions: when, and how, to step out of the sales seat w...

5 Maalis 52min

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