197. Rav Dhaliwal, Investor and Limited Partner, Crane - CS Meets Revenue: AI, Agents, and the New Customer Success
The SaaSiest Podcast21 Okt 2025

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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163. Matt Lerner, Founder & CEO, SYSTM - Why creating new categories could be killing your startup’s growth

163. Matt Lerner, Founder & CEO, SYSTM - Why creating new categories could be killing your startup’s growth

Think you need to create a whole new category to win? Think again. In this episode of the SaaSiest Podcast we had a chat with Matt Lerner, the founder & CEO of SYSTM and a seasoned tech and venture ca...

5 Nov 202451min

162. Birte Steen, Fractional CRO, Centra - The unstoppable formula to drive scalability and growth in SaaS

162. Birte Steen, Fractional CRO, Centra - The unstoppable formula to drive scalability and growth in SaaS

In our latest episode, we’re joined by Birte Sten, the CRO at Centra and industry leader in SaaS. From her early days as a competitive swimmer to leading high-impact sales teams, Birte shares how she’...

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161. Saahil Karkera, Vice President of Customer Success, Oaky - Here is how CS teams can make the most of the whitespace opportunity!

161. Saahil Karkera, Vice President of Customer Success, Oaky - Here is how CS teams can make the most of the whitespace opportunity!

In this episode, we had an insightful conversation with Saahil Karkera, VP of Customer Success at Oaky, to explore how customer success is evolving into a critical driver of growth and efficiency in t...

22 Okt 202446min

160. Chris Cunningham, Founding Member & Head of Social Marketing, ClickUp - How to win the the SaaS Attention Economy!

160. Chris Cunningham, Founding Member & Head of Social Marketing, ClickUp - How to win the the SaaS Attention Economy!

In our latest episode of the SaaSiest podcast, Chris Cunningham, Founding Member & Head of Social Marketing, ClickUp, shares how you need to adapt your communication on Social Media to meet the needs ...

15 Okt 202459min

159. Gauri Chawla, SVP, Global Alliances Stibo Systems - Building Effective Partner Ecosystems for Growth

159. Gauri Chawla, SVP, Global Alliances Stibo Systems - Building Effective Partner Ecosystems for Growth

In our latest episode, Gauri Chawla dives into the pivotal role that partnerships play in fueling revenue growth for B2B SaaS companies. She shares insights on building structured partner ecosystems, ...

9 Okt 202432min

158. Gabriela Warren, CMO, Puzzel - The Evolving Role of a CMO in Tech

158. Gabriela Warren, CMO, Puzzel - The Evolving Role of a CMO in Tech

In our latest episode of the SaaSiest podcast, Gabriela Warren, CMO of Puzzel, shares her journey from political science to leading marketing in tech. She emphasizes the importance of seeing beyond ma...

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157. Gökçe Ceylan, Principal, Oxx - Decoding SaaS Success: Applying Math to Drive Strategy!

157. Gökçe Ceylan, Principal, Oxx - Decoding SaaS Success: Applying Math to Drive Strategy!

In this episode, we speak with Gökçe Ceylan, Principal, Oxx, the specialist SaaS investor. The firm's strategy is built around the concept of “Go-To-Market Fit”, developing a structure for thinking ab...

24 Sep 202444min

156. Adam Robinson, CEO, Retention.com & RB2B - How shall a CEO build a personal brand that drives business revenue!

156. Adam Robinson, CEO, Retention.com & RB2B - How shall a CEO build a personal brand that drives business revenue!

In this episode, we speak with Adam Robinson, CEO, Retention.com & RB2B , 20m+ in combined ARR and growing at a fast rate, fueled by a strong founder brand! We talked with Adam about how he has built...

17 Sep 20241h 2min

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