Miles Goldstein (00:00):
I want to talk to an agent, and I would sit there and shout on the phone—“agent! operator!”—and pound on this. So if your chatbot is that robotic, not understanding the background or the sentiment or whatever, I think that will frustrate customers.
When I call, it knows from my phone number what my history is, it knows that I’ve called five times this week over this particular issue. It changes the discussion. It’s no longer just a script. It’s now actually interaction, interacting.
Niraj Ranjan Rout (00:33):
Hello, everyone. Today our guest is Miles Goldstein. Miles is a seasoned support leader with over 20 years of experience in B2B SaaS. Most recently, he led mission critical and federal support at Okta where he built out premium support services for large enterprises and government customers.
He spent his career scaling support organizations across industries, always with a focus on high-impact customer experiences. Really excited to have you here, Miles.
Miles Goldstein (01:08):
Thanks, Niraj. I’m happy to be here and looking forward to this conversation.
Niraj Ranjan Rout (01:15):
Miles, a good starting point would be to talk about your approach to customer support. Maybe share how your background shaped the way you think about customer experience today.
Miles Goldstein (01:33):
Yeah, sure. For me, a lot of it comes down to how support has to feel real. Customers don’t want to be treated like a number. They don’t want to repeat their story five times.
When I think about building support teams, I always start with empathy. You need people who care enough to put themselves in the customer’s shoes. The technology is there to help, but it should never replace that human connection.
Niraj Ranjan Rout (02:10):
That makes sense. You’ve spent time leading large enterprise and government support at Okta, which comes with very high stakes. Can you share how that experience shaped your philosophy on premium support?
Miles Goldstein (02:30):
Absolutely. In federal support, downtime can have huge consequences. It’s not just about SLAs—it’s about trust. If you’re supporting mission critical customers, you need to anticipate problems before they even raise them.
That’s where proactive communication, strong processes, and the right people matter more than anything. Customers need to know you’ve got their back before they even ask.
Niraj Ranjan Rout (03:00):
You’ve mentioned before that chatbots, when not designed well, can really frustrate customers. Could you expand on that?
Miles Goldstein (03:17):
Yeah. Look, I’ve been on those calls where I’m yelling “agent, agent, operator” into the phone, hoping the system understands me. That frustration comes when the bot is too rigid—when it doesn’t understand context, sentiment, or history.
If the system knows I’ve already called five times this week about the same issue, the experience should be different. It should acknowledge that history. Otherwise, it’s just a script pretending to be a conversation. And that’s what makes customers lose patience.
Niraj Ranjan Rout (03:55):
So the difference is really between automation that feels robotic versus automation that feels intelligent?
Miles Goldstein (04:10):
Exactly. Automation should serve the customer, not block them. If it’s not reducing friction, it’s adding frustration.
Niraj Ranjan Rout (04:25):
When you describe that kind of frustration with bots, it’s easy to see how support can actually damage trust if not done right. How do you think companies should balance automation with the human element?
Miles Goldstein (04:45):
I think it starts with remembering the purpose. If your chatbot is just there to deflect tickets and reduce cost, customers will see right through that. They’re smart.
But if you use automation to give them quicker access to the right answer, or to route them faster to the right person, then it feels helpful. That’s when automation actually adds value instead of creating barriers.
Miles Goldstein (05:10):
And again, it comes back to context. If a customer has been dealing with an issue for days, you don’t push them back into a loop of canned responses. You get them to a human as fast as possible. The system should know when to step aside.
Niraj Ranjan Rout (05:40):
Right. So the system has to know when to get out of the way. That’s a powerful point.
Niraj Ranjan Rout (06:00):
Miles, you’ve been in support leadership for more than two decades. What have you seen change the most in how customers expect to be supported?
Miles Goldstein (06:25):
The biggest shift has been expectations around speed and personalization. Twenty years ago, if you sent an email and got a reply in 48 hours, that was fine. Today, customers expect a response in minutes—and they expect you to know who they are and what their history is.
Miles Goldstein (06:50):
The other big change is that customers now compare every support experience they have—not just within your industry. If Amazon or Uber gives them a seamless experience, they’re going to expect the same from their SaaS provider. The bar is being set by consumer companies, and B2B has to catch up.
Niraj Ranjan Rout (07:20):
That’s such an important point—the benchmark isn’t your competitors, it’s the best experience your customer has had anywhere.
Miles Goldstein (07:35):
Exactly. And that’s why empathy and context matter so much. If you treat a customer like just another ticket, you’ve already lost. They expect to be treated like a person, not a case number.
Niraj Ranjan Rout (07:45):
You’ve worked in environments where support was truly mission critical—like federal and enterprise customers at Okta. How did you structure your teams in those high-stakes situations?
Miles Goldstein (08:05):
In those environments, the structure has to be crystal clear. You can’t afford confusion about who owns what. We built tiered teams where everyone knew exactly where their responsibility started and ended.
Miles Goldstein (08:22):
The other thing we did was build a culture of anticipation. You don’t wait for the customer to raise an issue—you monitor, you detect patterns, you let them know what’s coming before they feel the pain. That’s how you build trust in a high-risk setting.
Niraj Ranjan Rout (08:45):
And I imagine that requires collaboration with other departments too—engineering, product, even finance sometimes. How did you ensure alignment outside of support?
Miles Goldstein (09:05):
That’s always the challenge. The way we solved it was by making the customer voice impossible to ignore. We didn’t just say, “Here’s a bug report.” We told the story—who it was affecting, what the consequences were, how it tied back to business outcomes.
Miles Goldstein (09:25):
When you put that context in front of product managers, or finance leaders, it becomes real. They see the human side of the problem, not just a number in a report. That’s how you get alignment.
Niraj Ranjan Rout (09:45):
Makes sense. So one question there, Miles: I understand you could rally your entire customer-facing team around this, but I imagine you’d need alignment from other departments too.
If your team is posting things in Slack, you need product to engage, you need tech to step in. How did you convince the rest of the company that it was worth their time to spend on support?
Miles Goldstein (10:05):
That’s a great question. Cross-departmental alignment can be tricky. One of the things I’ve found—especially as a leader in support—is that managing our Voice of the Customer program has been the best way to drive alignment.
Miles Goldstein (10:25):
What’s different about how we ran Voice of the Customer at Okta is that we always provided the story—the context—behind everything. When we said “customer,” it wasn’t just external customers. It was also internal customers: our CS team, our support team, even sales engineers.
Miles Goldstein (10:50):
In Voice of the Customer sessions, we’d meet every two weeks. Different teams would take the spotlight each session and present one key issue impacting the customer experience. The impact was huge. It gave everyone shared context, a shared language. That’s how empathy builds—not just for the end customer, but across functions.
Niraj Ranjan Rout (11:37):
Can you tell us more about this Voice of the Customer program? Did you start it, or inherit it and evolve it? And how did you get other teams to contribute?
Miles Goldstein (11:52):
Yeah, for sure. So it was definitely a program I inherited. Initially, it was very focused on Net Promoter Score (NPS). Every week we’d meet, look at the NPS, review comments, slice the data in different ways—it was very data-focused. Not that we moved away from that entirely, but back then it felt more like a readout.
Miles Goldstein (12:20):
When I took it over, I wanted to make sure the information we were sharing was actually actionable and useful to the people hearing it. So we started putting storytelling behind the data.
Miles Goldstein (12:35):
To get more cross-departmental involvement, we didn’t just rely on our public Slack channel, though that was a huge part of it. I also started reaching out individually to leaders to ask if they had something valuable to share.
Miles Goldstein (12:50):
One example: we had a Learning Solutions team that worked closely with our authors. Historically, they weren’t always looped into product development or org-wide updates. I reached out, showed them an example from another team’s Voice of the Customer session, and asked if they’d like to present. From just that one reach-out, they started requesting more sessions to share what they were hearing. That was a win.
Miles Goldstein (13:20):
Also, the Voice of the Customer program wasn’t just about pain points. We shared positive stories too—examples of when things went right. Sessions were primarily attended by customer success teams and product managers. Sometimes engineers joined. And spinoff initiatives were born out of those sessions. It really became a cultural pillar.
Niraj Ranjan Rout (13:38):
So from what I understand, it essentially involves the entire company now. Do you run themes by team, or a single topic that everyone joins?
Miles Goldstein (13:50):
It’s a single meeting, held twice a week. Different teams are invited to spotlight their focus area during each session.
Miles Goldstein (14:05):
We also started sharing a short one-to-two-page internal newsletter for non-customer-facing teams, especially those that might not attend live. It was mainly for functions like finance. The newsletter included NPS updates, a few customer comments, and some light AI-powered analysis—what customers were saying, patterns that were emerging, and possible next steps.
Niraj Ranjan Rout (14:36):
Makes sense. One thing I’ve always found powerful in these sessions is anecdotes. You can have three pages of graphs, but one customer story lands harder. Do you focus on that?
Miles Goldstein (14:49):
Yeah, for sure. We invited our customer success managers—they usually had the best stories. We asked them to share what they were seeing and hearing.
Miles Goldstein (15:05):
Beyond Voice of the Customer, we also liked sharing “zero to hero” stories. A customer who started off unhappy but, through the efforts of multiple teams, became an advocate. That kind of turnaround story is gold.
Miles Goldstein (15:25):
You nailed it—it’s about the story. The data matters, but the narrative is what gives it weight and makes it memorable.
Niraj Ranjan Rout (15:58):
Great. Good to learn all that. One thing that intrigued me was your experience across different sectors—telecom, engineering, and EdTech. What common threads have you noticed? And how does customer behavior or employee behavior shift across those industries?
Miles Goldstein (16:15):
That’s a great question. If anything, there are a lot of similarities across those sectors. The most successful teams are the ones that consistently empathize with the customer.
Miles Goldstein (16:30):
Now, empathy isn’t something you can really teach—it’s more of an innate skill. But you can encourage people to be more understanding of someone’s situation. And you do that by giving them context.
Miles Goldstein (16:45):
In engineering, for instance, at my previous company I worked with a lot of junior developers. They were brilliant technically, but not always customer-focused. And that’s okay—not everyone has to be great at both.
Miles Goldstein (17:05):
But when you find someone who is technical and empathetic, that’s rare. That’s your unicorn. What we did was structure our team accordingly. If someone was deeply technical but not as strong with customers, we gave them roles that fit. Those who had strong customer instincts got a different growth path.
Miles Goldstein (17:30):
At Top Hat, our product is complex, but it doesn’t require agents to write code. That means we can find people who are comfortable reading and understanding technical documentation but also bring that customer-centered mindset. That blend—being technical enough, but also empathetic—is what makes growth paths more strategic and more meaningful. You don’t have to sacrifice one for the other.
Niraj Ranjan Rout (17:45):
Makes sense. And given your experience hiring across roles and sectors, how do you assess something abstract like empathy? What’s worked for you over the years?
Miles Goldstein (18:00):
Yeah, that’s a great question. Early on, I didn’t have much of a system. But over time, I’ve refined my approach. I now have a list of go-to questions that help assess different skills, including empathy.
Miles Goldstein (18:20):
One of my favorite prompts is this: “Pretend I know nothing. Pick a hobby or something you’re really into, and explain it to me like I’m a complete beginner.”
It’s so telling. You learn if someone can break down complex information. That’s a proxy for empathy, because it shows they’re thinking about the other person’s perspective.
Miles Goldstein (18:45):
You also learn about their interests, which helps with team dynamics. And you see how they communicate. Can they simplify? Can they stay engaging?
Miles Goldstein (19:00):
Another big one is curiosity. I think that’s the trait that separates a good agent from a great one. So I’ll ask: “Is there anything I haven’t asked that you wish I had?” or “What’s something you’d want me to know before this interview ends?”
Miles Goldstein (19:20):
That sounds simple, but the way people answer gives away a lot—how reflective they are, what they’re curious about, and whether they care enough to go deeper.
Niraj Ranjan Rout (19:45):
That’s such a great framework. I love how practical it is. Let’s switch gears for a bit. You mentioned earlier that when a company doesn’t value support, it becomes reactive instead of strategic. For CX leaders in that kind of setup, where support is still seen as a cost center, what can they do to change that perception?
Miles Goldstein (20:08):
Honestly, sometimes the best move is to leave. I know that sounds harsh, but if leadership doesn’t value support in 2025, they’re probably not going to suddenly start now. The longer you stay, the more you validate their mindset.
Miles Goldstein (20:28):
Be honest with your team. Tell them this isn’t normal. Help them see what great support orgs look like.
Miles Goldstein (20:40):
Of course, not everyone can just leave immediately. So while you’re there, build the case. Gather stories. Track impact. Share wins. But if you’re hitting a wall, don’t let it define your career. There are companies that do see support as strategic. Go find them.
Niraj Ranjan Rout (21:03):
I appreciate the honesty. Now let’s flip that around. Say you’re a founder or executive who wants to put CX at the center. What should they be doing differently?
Miles Goldstein (21:17):
Start with your roadmap. How much of it is based on customer input? How much tech debt are you addressing?
Miles Goldstein (21:28):
Then look at who’s in the room. If your support leaders aren’t part of product meetings, launch planning, or marketing campaigns, you’re not customer-obsessed, no matter what you say.
Miles Goldstein (21:45):
Also, think about how often you see your customers. Are you joining support calls? Are you reading tickets or NPS responses? Your words matter less than your actions.
Niraj Ranjan Rout (22:09):
Let’s talk about AI. It’s been a big part of the conversation in support teams lately. What’s your take—how should teams approach AI over the next few years?
Miles Goldstein (22:23):
AI can be amazing, but it shouldn’t talk to customers without strict QA. You can’t blindly trust a bot.
Miles Goldstein (22:33):
Where AI really helps is in freeing up time. I used to spend 40 hours a month manually analyzing tickets. Now, AI tools can do that for me—without bias—and I can focus on the bigger picture.
Miles Goldstein (22:50):
Instead of labeling tickets, I’m coaching my team. Instead of pulling reports, I’m joining strategic conversations. But it only works if you’ve built trust in your team.
Miles Goldstein (23:05):
If you’re hiring skilled CX professionals and giving them nothing but repetitive work, you’re wasting their talent. Let AI handle the grunt work. Let your people do what they’re best at—helping customers and improving the product.
Niraj Ranjan Rout (24:10):
That’s a great perspective. One final question before we wrap: What’s one thing you wish more people understood about support leadership?
Miles Goldstein (24:24):
That it’s hard—and that it matters. Support leaders constantly juggle priorities, react to issues, and advocate for both customers and their team.
Miles Goldstein (24:40):
But because it’s often invisible work, it’s easy to overlook. So if you work with a great support leader, tell them. Recognize it. Invest in it. Because when support is strong, everything else gets stronger too.
Niraj Ranjan Rout (25:04):
That’s such a powerful note to end on. Miles, thank you so much for being here and sharing your insights. It’s been a pleasure.
Miles Goldstein (25:12):
Thank you so much. This was such a thoughtful conversation. Really appreciated it.
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