Automating Grunt Work to Enable Strategic CS

What if the function you were about to join didn’t really exist yet?

In 2014, customer success was barely a function—it was an idea in the making. Omer Rabin took a bet on that idea at a time when the industry still needed convincing that managing customer relationships deserved its own tech stack. He went on to become Gainsight’s Chief Evangelist when most people thought “customer success” sounded like corporate cheerleading.

Fast forward a decade, and customer success has grown into a multi-billion-dollar industry. But somewhere along the way, many CS teams drifted from their strategic roots, becoming reactive order-takers buried in grunt work.

In this episode, Omer Rabin (General Partner at TLA Ventures) and Chad Horenfeldt (VP of CS at Siena AI and author of The Strategic CSM) discuss the past, present, and future of customer success. They take us back to the early days—Pulse local events on Toronto rooftops, the hunter vs. farmer debate, and how Nick Mehta’s pitch about “selling to existing customers” helped create an entire category.

WHAT YOU'LL LEARN:

• Why customer success emerged as a distinct function (and why it almost didn't)

• How CS teams lost their strategic edge—and how to reclaim it

• Why AI is bringing CS back to its strategic roots by eliminating grunt work

• Why Omer believes the next generation of CEOs will come from customer success

• Chad's framework for future customer intelligence

• The one question every CSM should ask to align with their CEO's top priority

---

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

---

Where to Find Chad:

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

The Strategic CSM: https://www.strategiccustomersuccess.com/

Where to Find Omer:

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

Where to Find Josh:

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

---

In this episode, we cover:

0:00 – Preview & Introduction

1:24 – Meet Chad & Omer

2:10 – Pulse Local Events and Building the CS Community

3:52 – Chad’s Origin Story: Being an Early CS Ambassador

4:55 – From Customer Cheerleading to Value Creation

12:45 – The AI Revolution and the Return of Strategic CSMs

18:31 – How Outcome-Based CS Influences Revenue

23:53 – Defining Success Is a Challenge

25:25 – How AI Analyzes Survey Data to Find Customer Sentiment

28:10 – Customizing Product Updates for Customers

29:25 – Tactical Advice for CSMs

30:35 – Aligning with Company Needs