Customer Support Leaders
Customer Support Leaders have been there, on the front line with customers. They understand how things work, and the value of support. They understand the needs and foibles of their customer base. Unlike most other disciplines, there’s no training for this role. No two CS Leadership roles are alike. No two CS Leaders are alike. So this is our opportunity to hear from those leaders and learn from them. Whether you’re a CS leader now, or you aspire to be, this is the podcast for you! Hear different leaders discuss a topic with me, Charlotte Ward.
Episodes
366 episodes
303: Practically Perfect Support; with Jason Yun
Mary Poppins is “practically perfect” and that makes her a surprisingly useful guide for modern customer support leadership. We (Charlotte Ward and Jason Yun, Head of Provider Success at Prax Health) use the film’s songs and characters to trans...
302: Using AI to identify coaching opportunities; with Rob Dwyer
Most coaching goes wrong before the coaching conversation even starts. If we only review a tiny sample of calls, chats, or tickets, we end up “coaching the seventh hole” and missing the real issue that shows up earlier in the customer journey, ...
301: Using AI To Make Us Better Managers; with Reagan Helms
Your calendar says “1:1s,” but your brain hears “context switching.” Charlotte Ward sits down with Reagan Helms, VP of Customer Experience at Planning Center, to unpack a practical way AI can make us better managers: a management assistant that...
300: Reflecting on the Year So Far; with Alec Moloney
A lot has changed since the start of the year and not just job titles and cities. Charlotte Ward sits down with returning guest Alec Maloney to take stock of what is actually happening inside modern customer support teams as AI, automation, and...
299: AI Won't Fix Your Knowledge Quality Problem - It'll Expose It; with Leslie O’Flahaven
AI can generate a clean looking knowledge article in seconds, but that speed comes with a trap: it makes bad knowledge easier to publish and easier to surface. Leslie O’Flahavan joins me to unpack a simple claim with big consequences for custom...
298: Returning to the Office; with Andrew Rios
The office can be a productivity killer or a leadership advantage, and the difference usually comes down to one thing: whether we design the day or let the day design us. I’m joined by Andrew Rios to get real about returning to the office after...
297: AI Beyond The Queue; with Robert Cabral
AI in customer support gets reduced to one tired idea: ship a chatbot and cut tickets. That mindset misses where the real leverage is. We sit down with Robert Cabral, Head of Customer Experience at Runway, to talk about “AI beyond the queue” an...
296: Flipping Away From Leadership; with Jenny Dempsey
Getting laid off can scramble more than your finances. It can shake your identity, your confidence, and the story you’ve been told about what “success” in customer support leadership is supposed to look like. That’s why this conversation with J...
295: Fearless CX; with Nate Brown
Customers are talking about you where your VOC program rarely looks and it’s shaping revenue, retention, and trust. Nate Brown joins me to introduce Fearless CX, a bold and practical way to lead customer experience in a time when fear is high, ...
294: What Support Does When AI Takes The Tickets; with Ryan Klausner
AI is starting to take the queue. So what’s left for a customer support team once automation handles triage, repetitive questions, onboarding, and a big chunk of ticket volume? Ryan Klausner joins me to get specific about “life after AI” and wh...
293: Roles AI is Creating in Support; with Hilary Dudek
AI is already in your support queue, but the real question is what it’s doing to your career path. I’m joined by Hilary Dudek, Head of Customer Experience at Gamma, to get specific about how AI is reshaping customer support roles and why the “b...
292: Tailoring Your Coaching as People Grow; with Andrew Rios
Growth rarely happens on a straight line, and neither should coaching. We sat down with Andrew Rios, Head of Customer Experience at Cityside Fiber, to explore how leaders can tailor their coaching as people mature—from fresh hires forming their...
291: The Changing Identity of Support; with Lauren Eimers
What happens when AI automates the work that built your career story? We sit down with Lauren Eimers to trace a path from clinical counseling and genetics into customer support leadership and onward to clinical science liaison, then use that jo...
290: From Timelines To Fit: Making Smart Support Hires; with Matt Dale
Hiring plans look clean on a roadmap until real candidates, real timelines, and real markets show up. We unpack a practical, humane approach to building a support team that can handle peak seasons without sacrificing quality: plan backwards fro...
289: Cultivating Customer Champions; with Greg Skirving
What if a “ticket” isn’t a ticket at all, but an engagement where both sides own the outcome? We sit down with Greg Skirving to unpack how customer champions transform support from reactive break fix to a partnership that moves faster, learns f...
288: Support in a High-Trust Environment; with Simone Secci
Trust isn’t a slogan when failure has real consequences. Simone Secci joins Charlotte Ward to pull back the curtain on support operations in two intense arenas—concierge‑level luxury tourism and clinical psychology platforms—and find a shared b...
287: Extreme Delegation: How To Lead When Everything Changes At 4 PM On An Idle Tuesday; with Matt Dale
A quiet Tuesday turns into a leadership stress test. We share the playbook for extreme delegation—those moments when a key lieutenant leaves, the CEO secondments you into a new role, or a surprise launch forces you to hand off mission-critical ...
286: Measure What Matters When Humans And AI Share The Queue; with Craig Stoss
AI has crossed a threshold in customer support: it no longer just routes and records—it actually does the work. We sat down with Craig Stoss, solutions lead at Codif, to unpack what changes when agents and co-pilots resolve real cases, trigger ...
285: From Playbooks To Personalization: How CX Leaders Shape Customer Expectations And Outcomes; with Ty Givens
Superior customer experience isn’t a universal recipe—it’s a promise aligned to what your customers expect from you, in their moment, on their terms. We sit down with CX veteran Ty Givens to unpack why “good” is always relative and how teams ca...
284: Customer Support Leaders in 2026: Fresh Starts and More To Come; with Charlotte Ward and Alec Moloney
Ready for a clean slate and a smarter way to build support in 2026? We kick off a fresh season with a rebuilt website, renewed energy, and a clear map of the big shifts reshaping our work: AI moving from side experiment to operational backbone,...
283: From Values To Outcomes: Building A Customer Support Strategy That Works; with Conor Pendergrast
Forget the glossy strategy deck. We’re digging into the real drivers of customer experience: the values people use to decide, the culture that shows up in daily behavior, and the incentives that shape how work actually gets done. With coach and...
282: Turning Difficult Customer Moments Into Lasting Trust; with Marc Haine
Ever faced a customer whose day went off the rails before they reached you? We dive into the emotional mechanics of difficult conversations and show how empathy, clear choices, and a partnership mindset can turn even the messiest moments into m...
281: Accuracy Beats Hype - Building Trustworthy AI With KCS; with David Kay
What if the fastest path to trustworthy AI starts with a better knowledge base? David Kay is Principal at DB Kay & Associates, a consultancy focused on knowledge management and self-service f...
280: Mastering Incident Management - Part 6 of 6; with Kat Gaines
Outages test more than systems—they test culture. We dig into what “calm under pressure” actually looks like, from the first hint of trouble to the final post‑incident review. Together with guest Kat Gaines of PagerDuty, we explore why support ...
279: Is AI Overcooked in Support?; with Rob Dwyer
Sauce jokes aside, we get real about AI in customer support: why it’s tempting to chase the trend, how early demos can mislead, and what actually works once you bring models into day-to-day operations. Rob Dwyer joins us to unpack the differenc...