This week, I sat down with Sydney Chestler, Director of CX at Fresh Clean Threads, to talk about what it really takes to build trust in customer experience, not just close tickets.

We get into what it means to lead CX at two wildly different brands, from helping a 25-year-old skincare fan find her first serum to supporting a 45-year-old dad buying tees for vacation. Sydney shares how she’s built a career around understanding what customers actually care about and how to design experiences that feel human, honest, and clear.

We cover the shift from reactive support to proactive CX, the importance of tracking “silent wins” like low ticket-to-order ratios, and why transparency should be your brand’s default setting. Sydney breaks down why the best metric isn’t how many tickets your team closes, it’s how many you prevent by setting the right expectations.

We also talk about leadership. Sydney opens up about how mentors shaped her career and how she now pays it forward by building teams that feel heard, supported, and empowered. Her approach is rooted in empathy and connection, and it shows up in everything she does, from team culture to how she thinks about the customer journey.

If you care about building trust, leading with transparency, and empowering your CX teams to do their best work, this episode’s for you.

Listen now for insights on leadership, trust, and how to turn every touchpoint into a relationship, not just a transaction.

📲 Follow Sydney:

Linkedin: https://www.linkedin.com/in/sydneychestler/

📲 Check out Fresh Clean Threads:

Linkedin: https://www.linkedin.com/company/fresh-clean-threads/

Website: https://freshcleantees.com/

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