Who’s Got This If You’re Out? – Miles Goldstein on Building Bulletproof Support

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 Miles Goldstein
  • 💬 What would your support alter ego be called—and what would their superpower be?
  • 🎯 How did you find your way into customer support — was it accidental or intentional?
  • 🌀 The weirdest or most unexpected support request you’ve handled?
  • 🧩 What’s one practical change you’ve made to improve customer-centricity?
  • 📊 One tool you can’t live without at work?
  • 🧠 One piece of advice for someone just entering the support world?
  • 🤖 A use case where AI actually made things better?
  • 📬 Is email underrated or overrated as a support channel?
  • 🎬 A book, podcast, or show you’d recommend to fellow CX folks?
  • 🙅‍♂️ Your go-to emoji with customers?
  • 🎸 If you weren’t working in CX, what would you be doing?

In Conversation With Miles Goldstein

Miles Goldstein is a Global Product & Technical Support Executive who’s helped scale enterprise support functions at companies like Okta, Amobee, and Turn. With decades of experience, he’s built support teams from the ground up, reduced escalations by designing airtight incident workflows, and led premium support programs for high-value clients.

But for Miles, customer support is more than just the processes. It’s about knowing when to be a teacher, a detective, or even a friend, depending on the moment. He calls it “wearing many hats,” and it’s a mindset that’s helped him deliver support that’s responsive and deeply human.

In this edition of CX Spotlight, Miles shares the importance of having named backups for designated support, why email still reigns supreme, and what Monty Python has to teach us about customer service.

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

I’d be “Doc”, someone who can cut through the noise and get right to the heart of the issue. Whether it’s a messy escalation or a vague support request, Doc doesn’t get distracted. He diagnoses fast and prescribes solutions with precision.

🎯 How did you find your way into customer support — was it accidental or intentional?

Completely accidental. I actually wrote about it here: The Accidental Career

What started as a side step into support turned into a long, fulfilling career. I’ve built and led global teams, launched service programs, and become a driver of customer retention – all because of that accidental start.

🌀 The weirdest or most unexpected support request you’ve handled?

A customer from another software company (one that’s notorious for constantly changing its own product) reached out to complain that we had changed our UI.

It was a true “do you understand how software works?” moment.

🧩 What’s one practical change you’ve made to improve customer-centricity?

For customers who paid for a Designated Support Engineer (DSE), we introduced explicit named backups. That way, even when the primary DSE was out, the customer still had a trusted point of contact who knew their account. It helped us preserve the value of that 1:1 relationship while adding resilience to the support experience.

📊 One tool you can’t live without at work?

Excel – hands down. One of my companies even tried to take it away, but I fought to keep it. Our own product relied on Excel for imports and exports. Plus, I use it constantly for reporting, analysis, and even organizing thoughts. It’s still essential.

🧠 One piece of advice for someone just entering the support world?

You’ll need to wear many hats — and learn when to switch them. Some days, you’re a techie. Other days, a teacher, therapist, detective, or partner. Knowing how to shift roles quickly and appropriately is what separates good support professionals from great ones.

🤖 A use case where AI actually made things better?

My teams haven’t fully embraced AI yet, but I think its most immediate value is in navigating tools and knowledge bases.

Having AI surface known answers quickly, especially across fragmented systems could be a massive time-saver. That’s where I see us heading next.

📬 Is email underrated or overrated as a support channel?

Underrated, and still my first choice.

With email, you get screenshots, logs, copy-pasteable error messages, and a clean audit trail. Voice and chat can be great, but they often lack the detail and traceability that email offers, especially when dealing with complex technical issues.

🎬 A book, podcast, or show you’d recommend to fellow CX folks?

A training film called “Who Sold You This Then”, made by Monty Python’s John Cleese.

It’s old-school, but packed with timeless lessons on how not to treat customers. Funny and effective.

🙅‍♂️ Your go-to emoji with customers?

Honestly… none. I’m a Baby Boomer, and emojis in professional customer conversations still feel a little out of place to me 🙂

🎸 If you weren’t working in CX, what would you be doing?

I’d be playing guitar.

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