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Niraj Ranjan Rout (00:59):
Welcome to the podcast. Today, I’m excited to have Sarah Caminiti with us. Sarah is the Manager of Customer Support at Tailscale. Tailscale is revolutionizing secure networking with its easy-to-use, zero-config VPN service. At Tailscale, Sarah focuses on delivering an exceptional customer experience while also optimizing operations behind the scenes. Her team doesn’t just solve problems — they work toward enhancing the overall product experience.
Beyond her role at Tailscale, Sarah is also a career strategist, consultant, and mentor. She helps CX professionals navigate leadership and career challenges. She also hosts the Career Strategist Podcast (formerly Epical Growth),where she dives into topics like leadership, career transitions, and the evolving landscape of customer experience. Welcome to the podcast, Sarah. Really looking forward to the conversation.
Sarah Caminiti (02:05):
Thank you! I’m so pumped to be here. This feels very full-circle — my whole journey as a public-facing person started with Hiver, and it’s an honor to continue this relationship and have this conversation. Thanks for making it through my multi-layered intro. I’m realizing I might need to take a vacation or start saying “no” more often. But I appreciate you.
Niraj Ranjan Rout (02:34):
Absolutely. Great to have you here. Let’s start at the beginning. How did you get into CX? What was your journey like, and how did it lead to your current role at Tailscale?
Sarah Caminiti (02:59):
Do you have 17 hours? I’ll try to make it brief. Like many CX veterans, I didn’t land here by choice. Customer support in tech wasn’t seen as a career option when I started. But I’ve always been in and around customer experience in one form or another. I’ve even tried to run from it — thinking I couldn’t build a career I loved in it.
Then I found SaaS. I found remote work. I found startups. And I realized I’m a builder. Collaborating with people from all over the world to create something meaningful — and helping others succeed — is what connects all the dots in my career. Leading teams, being the kind of leader I always wanted, and showing others that you can lead differently has been a great journey.
Niraj Ranjan Rout (04:09):
Love that. CX is such a multifaceted role — what parts of it are the most exciting to you?
Sarah Caminiti (04:16):
There are definitely parts I don’t love — it’s not a perfect space. But I love listening to customers. I love digging into data, doing root cause analysis, and experimenting. Creating a safe space for teams to experiment is huge.
In CX, you’re talking to people who are struggling, who feel embarrassed because they can’t figure something out. And if you can positively impact their day — and teach your team how to do that — it’s really powerful. You can take those moments, the insights, and bring them to product.
So when a customer says, “This doesn’t work for me,” or, “Why did you change the color of this button?” — that feedback becomes a tool. It helps you build something better.
Niraj Ranjan Rout (06:35):
That totally resonates. CX really is this blend of left-brain and right-brain — empathy and analysis. How do you hire for something like that?
Sarah Caminiti (07:11):
Hiring is a wild ride. I’ve learned a lot from failing. What seems obvious often isn’t. I focus less on resumes or cover letters and more on writing prompts. Simple scenarios like: “A customer forgot their password. How do you approach it?”
In a past role, I trained engineers in all-hands support. They were brilliant but not always great communicators. I helped them structure their replies, explain things clearly, and write empathetically. We’d start with practice scenarios, compare answers, and learn from each other.
You don’t always need industry experience. If someone knows what “good” looks like and can communicate well — that’s what I look for.
Niraj Ranjan Rout (09:26):
You also said something important earlier — everyone is in support. The better you are at it, the better the company gets.
Sarah Caminiti (09:35):
Exactly.
Niraj Ranjan Rout (09:36):
Let’s go back to data. You mentioned using data to drive change. Can you walk us through how you do that?
Sarah Caminiti (10:02):
When I realized how powerful support data was, it changed everything. Before AI tools, I created my own 15-point spreadsheet and manually analyzed every interaction.
I looked for broken docs, patterns across engineering teams, even sales opportunities. It wasn’t about auditing agents — it was about solving the real problem. And if something wasn’t working, it was on me to figure out why.
When your team feels safe to ask questions, the customer feels safe too. And that safety is what leads to better data, better products, and ultimately a better company.
Niraj Ranjan Rout (12:11):
That’s a great learning. The impact of CX goes far beyond just the support team. It touches every part of the business.
Sarah Caminiti (13:14):
Yes. And how support is treated often depends on how leadership views it. If the C-suite sees it as a task anyone can do, it’s underfunded, understaffed, and undervalued.
By the time they bring in someone to “fix support,” the damage is already done. Early customers already formed an impression. You’re playing catch-up.
But when companies truly value support — when it drives product, marketing, and sales — it changes everything. Those teams are heard, supported, and part of the strategy.
Niraj Ranjan Rout (18:04):
So if you’re a CX leader in a traditional, undervalued setup — what do you do? How do you change that culture?
Sarah Caminiti (18:43):
Honestly? I don’t think you should try. Find a job where you’re respected. If leaders still don’t care about CX in 2025, they’re not going to. Staying just validates their mindset.
Be honest with your team. Tell them this isn’t normal. And don’t wait around for change that won’t come.
Niraj Ranjan Rout (20:29):
That’s bold, but fair. Let’s flip the question — how can leaders like me put CX at the center of everything?
Sarah Caminiti (20:52):
Start with your roadmap. How much of it is based on customer input? How much tech debt are you addressing?
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.
Niraj Ranjan Rout (23:04):
Let’s talk about AI. What’s your take on its impact in support over the next 3–5 years?
Sarah Caminiti (23:04):
AI can be amazing — but it shouldn’t talk to customers without strict QA. You can’t blindly trust a bot.
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 — with zero bias — and I can focus on analyzing the trends, supporting my team, and joining strategic conversations.
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 team do what they’re best at — helping customers and shaping the product.
Niraj Ranjan Rout (27:42):
That makes perfect sense. Sarah, this has been such an insightful conversation. Thank you for sharing so generously.
Sarah Caminiti (27:44):
Thank you! This was a great experience. Big fan of Hiver — I’m excited to see what’s next for you.
Niraj Ranjan Rout (27:52):
Thank you.
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