Building Trust, Not Just Tickets: A CX Conversation with Sydney Chestler of Fresh Clean Threads

Some brands treat customer experience like a checklist. Sydney Chestler treats it like a relationship.

This week on Above the Fold, I sat down with Sydney Chestler, Director of CX at Fresh Clean Threads and former Glossier alum, to talk about what it really takes to earn a customer’s trust. From helping a 25-year-old skincare fan find her first serum to supporting a 45-year-old dad buying tees for vacation, she’s learned that great CX isn’t about scripts or systems, it’s about understanding what people actually care about.

CX Isn’t One Size Fits All

When Sydney transitioned from Glossier to Fresh Clean Threads, she had to unlearn some habits. What mattered to beauty buyers wasn’t the same for apparel shoppers. “A 25-year-old woman buying skincare for the first time has such different needs than a 45-year-old man buying T-shirts,” she said. “You have to shift your mindset.”

Her point? The customer journey looks different for everyone, and mapping it out is non-negotiable. It’s not just about acquiring users; it’s about anticipating how they think, feel, and behave from the first click to their next purchase.

Listening Beyond the Loudest Voices

We talked about how easy it is to focus on the loud customers, the ones who leave reviews or reach out with complaints. But as Sydney reminded me, “We’re missing all of the customers who didn’t want to engage with us, whether for positive or negative reasons.”

That’s where her data-driven mindset shines. She doesn’t just look at CSAT or NPS; she studies ticket-to-order ratio, the number of tickets per order, to find silent brand champions. If people aren’t reaching out, it often means the experience worked. And when those customers come back months later without ever contacting support? That’s CX done right.

Building Trust Through Transparency

When I asked Sydney what her North Star is, she didn’t hesitate: trust.

In her words, “You have to build trust with the customer at every touchpoint. That means being authentic, being clear, and being transparent.” Whether it’s pre-order delays or unclear shipping timelines, her team’s philosophy is simple, underpromise, overdeliver, and always communicate.

She explained how small details, like adding two extra processing days to an estimated delivery window, can make all the difference. “If you tell customers upfront, they trust you. But when you don’t, you create ambiguity, and that’s how you lose them.”

CX Is a Company-Wide Effort

Sydney and I couldn’t agree more on this: CX isn’t a department. It’s a lens for how the entire company operates.

Too often, businesses isolate CX as an afterthought, the cleanup crew for growth gone wrong. But Sydney’s approach is holistic. “You have to have people in every department thinking about the customer,” she said. “Why do we do anything as an organization? It’s for them.”

That mindset has carried her from her first CX agent role at Glossier to now leading a full team at Fresh Clean Threads. She credits mentors like Janie Cormier for helping her find her leadership style, one rooted in empathy, curiosity, and empowerment.

Leading with Empathy (and Data)

Sydney doesn’t believe in fitting people into boxes. She leads by finding out what excites her team and aligning that with business goals. “If someone’s really into writing, have them craft empathetic macros. If they love logistics, let them work on fulfillment.”

That flexibility doesn’t just build better teams, it builds better experiences. Because when people feel supported, customers do too.

The Future of CX

Looking ahead, Sydney is optimistic about AI’s role in CX. But not as a replacement. “AI should take on the nuts and bolts,” she said, “so humans can focus on the higher-level, holistic work.”

She sees technology as a way to enhance empathy, not erase it, freeing teams to spend more time building trust, analyzing feedback, and collaborating across departments.

Her legacy goal? Simple but powerful: to make sure CX professionals have the tools they need to actually help customers. “I want my team to feel supported so that customers feel supported,” she said.