CX Spotlight: Michael Windler on Small Habits that Change Call Quality & What Customers Actually Remember

CX Spotlight is a series where we speak to customer experience leaders from across industries who are rethinking support, building customer-first cultures, and finding clarity in the messiness of real-life CX.

Every edition is a quick, candid conversation. No fluff. No jargon. Just real-world insights from people who’ve been there and done that.

Table of Contents

• 👉 In Conversation With Michael Windler
  • 1. What would your support alter ego be called—and what would their superpower be?
  • 2. Tell us how you found your way into the world of customer experience
  • 3. The weirdest or most unexpected support request you’ve ever handled
  • 4. What’s one practical change you’ve implemented to make your team more customer-centric?
  • 5. What’s one tool or app you can’t live without at work?
  • 6. One piece of advice you’d give someone entering customer support
  • 7. What’s a use case where AI actually made things better?
  • 8. A book, podcast, or show you’d recommend to your peers
  • 9. If you weren’t in CX, what would you be doing?

👉 In Conversation With Michael Windler

Michael Windler has spent over 20 years leading high-volume B2C customer support operations. Most recently, as Head of Member Services at Tangelo, he introduced AI-automation that cut operating costs by 50%+ and increased weekly activations by 30% in his first month.

Across roles at Flossy, Atom Tickets, and 1-800-Dentist, he focused on fixing the systems behind support. By closing product gaps and broken workflows that drove repeat contact, he increased bookings by 40% in 90 days and raised CSAT above 90%.

In this edition of CX Spotlight, Michael talks about how small habits shape call quality and what Tulsa King teaches about leadership. He also shares an escalation call that took an unexpected turn after a customer asked for an agent’s mailing address.

1. What would your support alter ego be called—and what would their superpower be?

Captain Easy. My superpower is making every customer interaction feel intuitive and effortless. No confusion, no extra steps, just a clear and obvious path from question to answer.

2. Tell us how you found your way into the world of customer experience

It was completely accidental. I was working as a branch manager in financial services when my company launched a new internal helpdesk for a proprietary system rollout. My branch was part of the pilot. I volunteered to step in as a team lead.

I ended up spending most of my time helping frontline employees navigate change at scale. That experience pulled me into the contact center world, and once I was there, I never really left.

3. The weirdest or most unexpected support request you’ve ever handled

I once took what I thought was a serious escalation. It turned out the customer wanted my agent’s mailing address so they could send a thank-you gift for making their movie date special. A few days later, a box of classic theater candy showed up at our office. 

It was a good reminder that great support isn’t always about solving problems. Sometimes it’s about creating moments people remember.

4. What’s one practical change you’ve implemented to make your team more customer-centric?

Early in my career, we put small mirrors on every agent’s desk. Not to monitor them, just to remind them to smile on calls, because customers can really hear a smile. That small cue helped agents remember there was a real person on the other end.

5. What’s one tool or app you can’t live without at work?

ChatGPT. I use it as an always-available thought partner. Whether I’m structuring ideas or trying to explain something more clearly, it helps me think things through faster.

6. One piece of advice you’d give someone entering customer support

Focus on the people first. The tools and systems you use will keep changing, sometimes faster than you expect. But at the end of the day, customer support is still about people talking to people.

7. What’s a use case where AI actually made things better?

I’ve seen AI work best when it stays focused on the easy stuff. When self-service handles the simple, repetitive questions, customers get answers right away. That gives agents more room to focus on the conversations where a human actually makes the difference.

8. A book, podcast, or show you’d recommend to your peers

Keeping it light, I’d say the crime series Tulsa King. It’s a great escape, and it’s interesting to watch leadership and relationships play out in unexpected places.

9. If you weren’t in CX, what would you be doing?

I’d probably still be in consumer finance, where I started my career. Even back then, I was always drawn to the people side of the work. It’s hard for me to imagine doing anything else.

Enjoyed Michael’s take on customer experience? Connect with him on LinkedIn or check out more stories in the CX Spotlight series.

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