Fleetio’s vision: Free CSMs from transactional work

How do you manage 100,000+ renewals or scale AI across thousands of CSMs? CS leaders share how they're tackling their biggest challenges and using technology to drive retention, adoption, and efficiency.

In this episode of the [Un]churned Podcast, Josh Schachter sits down with customer success leaders at the 2025 Gainsight Pulse Conference in Las Vegas to explore how they're tackling their biggest challenges - from managing massive renewal volumes to driving adoption at scale. Featuring CS executives from Rockwell Automation, Fleetio, Handshake, Boomi, Dellteck, and SAP, this episode reveals practical strategies for using AI to save time, improve efficiency, and deliver better customer outcomes.

What you'll learn:

1. How Rockwell Automation's CS team manages 100,000+ annual renewals with 300 team members across 85 recurring revenue products

2. Why AI-powered engagement signals are replacing time-based customer outreach

3. The importance of building trust in AI-powered insights before teams will adopt them

4. How to aggregate and visualize data from multiple systems to tell a coherent story to stakeholders

5. Why change management is critical when introducing new product features that alter established workflows

6. How relationship-level insights can reveal the full picture of multi-product customer health

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Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/

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Where to Find the guests:

- Angel Rogers - https://www.linkedin.com/in/angel-rogers-leader/

- Sean MacPherson- https://www.linkedin.com/in/seanmacpherson

- Tiffany Taylor - https://www.linkedin.com/in/tiffany-taylor-learner/

- Matt Krebsbach - https://www.linkedin.com/in/matt-krebsbach-694117163/

- Charlie Ferraro - https://www.linkedin.com/in/charlesferrao/

- Margo Martin - https://www.linkedin.com/in/margomartin-/

- Tony Pante - https://www.linkedin.com/in/tony-pante-9b5419/

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Where to Find Josh:

LinkedIn: https://www.linkedin.com/in/jschachter/

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In this episode, we cover:

0:00 - Introduction

0:27 - Angel Rogers: Managing 100K renewals at Rockwell Automation

5:32 - Sean MacPherson: Aggregating insights from multiple systems

9:48 - Tiffany Taylor: Speed up feedback loops and time-to-value

14:09 - Matt Krebsbach: Prioritization, delivering outcomes and data enablement

18:47 - Charlie Ferraro: Retention, renewals and efficiency

20:35 - From Spidey sense to AI-powered engagement analysis

21:47 - Measuring adoption in agentic products

22:07 - Margo Martin: Stay ahead with real-time defect alerts

25:17 - The value of relationship-level insights

26:10 - Tony Pante: Driving adoption across 2,000 CSMs at SAP

29:35 - Using AI for translation, content creation, and enablement

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Referenced:

• Gainsight Pulse Conference: https://gainsightpulse.com/europe/

• Rockwell Automation: https://www.rockwellautomation.com/

• Fleetio: https://www.fleetio.com/

• Handshake: https://joinhandshake.com/

• Boomi: https://boomi.com/

• Dellteck: https://www.deltek.com/en

• SAP: https://www.sap.com/

• Staircase AI: https://www.gainsight.com/staircase-ai/

• Reef AI: https://www.reef.ai/

• Gong: https://www.gong.io/de/

• SAP Joule: https://www.sap.com/products/artificial-intelligence/ai-assistant.html