🎙️ Ep 3: When Customers Get Personal: Conor's Escalation Processes for Expensify

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This week on Live Chat with Jen Weaver, I sat down with Conor Pendergast, founder of CustomerSuccess.cx, to talk about one of the spiciest topics in customer support: escalations.

No, we’re not just talking about transferring tough tickets up the chain. Conor shared his experience at Expensify, where he led a game-changing escalation process that didn’t just move conversations—it protected agents, reinforced company values, and brought leadership into the mix.

To skip the summary below and go straight to the source:

🎙️ Listen now

🎥 Watch now

📑 Download the playbook and exec proposal

Here’s what stood out (and what you can steal for your own team):

🔥 The Problem

Conor’s team was facing a tidal wave of heated conversations. Customers would respond to political stances taken by the company, often targeting support agents with off-topic or abusive messages.

As a result, there was stress, confusion, and some agents were feeling unsupported, especially agents based outside of the US. It was clear: this wasn’t their burden to bear.

🔑 The Solution

Conor built a dual-layer escalation process that tackled the issue head-on:

1. Automatic Escalations: Using a keyword-triggered system, abusive messages were flagged and routed to senior leadership.

2. Manual Escalations: Agents were empowered to escalate conversations when they felt a line had been crossed—whether it was personal attacks, abusive language, or just a gut feeling.

The real kicker? Senior leadership, including the CEO, stepped up to handle these conversations directly.

💡 Lessons from Conor

• Escalations Are a Leadership Responsibility: By owning the tough conversations, leadership set the tone for accountability and showed their agents they were supported.

• Set Clear Boundaries: When conversations shift from the product or process to targeting individuals, it’s time to escalate.

• Psychological Safety Is Key: Protecting agents from undue stress is just as important as resolving customer concerns.

• Iterate and Improve: A keyword list isn’t one-and-done. Regular reviews helped refine the process and minimize false positives.

🎯 Actionable Takeaways

Ready to level up your support ops? Here’s how to get started:

1. Define Escalation Criteria: Establish clear guidelines for when conversations should be escalated.

2. Create Dual Escalation Paths: Use automated triggers for obvious cases and manual options for agent discretion.

3. Train and Empower Agents: Make sure agents know they’re not alone—and that leadership has their back.

4. Involve Leadership: Show customers (and your team) that your leaders are engaged and accountable.

🚀 Final Thoughts

What impressed me most about Conor’s approach is how it reinforced company values while fostering a healthier team environment. It’s not just about protecting your agents—it’s about showing them they matter.

Got spicy conversations in your queue? Try out some of these tips and let me know how it goes.

And don’t forget to listen to the full episode of Live Chat with Jen Weaver to hear Conor’s story in his own words. You won’t want to miss it!

🎙️ Listen now

🎥 Watch now

📑 Download the playbook and exec proposal

See you next time!
Jen Weaver
Host of Live Chat with Jen Weaver

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