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(210)

178. Maja Voje - GTM strategist and Best Selling Author - Why Every New Product (Especially AI) Needs an ECP Strategy!

178. Maja Voje - GTM strategist and Best Selling Author - Why Every New Product (Especially AI) Needs an ECP Strategy!

In this episode, we sit down with GTM strategist and best-selling author Maja Voje to dive deep into the concept of the Early Customer Profile (ECP) - and why it’s more important than ever in the AI e...

26 Maalis 202550min

177. Frederic Laziou, CEO, Puzzel - How to make the transition from a Feature Factory to an Outcome-Driven product approach!

177. Frederic Laziou, CEO, Puzzel - How to make the transition from a Feature Factory to an Outcome-Driven product approach!

In this episode, we speak with Frederic Laziou, CEO, Puzzel, a leading European provider of cloud-based contact center solutions, helping businesses deliver seamless customer service across multiple c...

19 Maalis 202554min

176. Maja Lindström, CPO, Talentech - Lessons learned from 8 acquisitions - The CPO perspective!

176. Maja Lindström, CPO, Talentech - Lessons learned from 8 acquisitions - The CPO perspective!

In this episode, we speak with Maja Lindström, CPO, Talentech, a leading developer of HR providing a seamless talent journey through a centralized platform. With main hubs in Oslo, Amsterdam, Stockhol...

5 Maalis 202553min

175. Mie Elmkvist Schneider, VP Sales & CS, Queue-it - The Sales Leadership KPI Dashboard!

175. Mie Elmkvist Schneider, VP Sales & CS, Queue-it - The Sales Leadership KPI Dashboard!

In this episode, we speak with Mie Elmkvist Schneider, VP of Sales & CS, Queue-it, a leading developer of virtual waiting room services, empowering 1,000+ organizations worldwide to build and nurture ...

27 Helmi 202556min

174. Marie Claire Silfer Head of Community Management, SaaSiest -  MC is in the house and here is why you should care!

174. Marie Claire Silfer Head of Community Management, SaaSiest - MC is in the house and here is why you should care!

This is a special episode with our very own MC, our new Head of Community Management over here at SaaSiest!  We're building this community in the open together with all of you, and in this episode, w...

19 Helmi 202539min

173. Nataly Kelly, CMO, Zappi -  AI or Die? How CMOs Can Prioritize AI Investments Under Pressure!

173. Nataly Kelly, CMO, Zappi - AI or Die? How CMOs Can Prioritize AI Investments Under Pressure!

In this episode, Nataly Kelly, CMO, Zappi, a leading consumer insights platform that connects brands with consumers. Through AI-powered software that delivers connected insights, Zappi empowers brands...

10 Helmi 202554min

172. Diane Wiredu,  Founder, Lion Words - Message-Market Fit: How much does your message resonate with your customer?

172. Diane Wiredu, Founder, Lion Words - Message-Market Fit: How much does your message resonate with your customer?

In this episode, we speak to Diane Wiredu, a messaging expert and the founder of messaging consultancy Lion Words. She's been helping SaaS companies for a decade to achieve 'message-market fit. So the...

29 Tammi 202557min

171. Dirk Sahlmer,  Head of Origination, SaaS Group - 3 reasons why nobody will buy your SaaS

171. Dirk Sahlmer, Head of Origination, SaaS Group - 3 reasons why nobody will buy your SaaS

In this episode, we speak to Dirk Sahlmer, Head of Origination, at SaaS Group, a conglomerate of independent SaaS businesses founded by experienced industry veterans with proven entrepreneurial, inves...

22 Tammi 202537min

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