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© 2026 Customer Support Leaders
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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.
360 Episodes
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Send us Fan Mail 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” and what it looks like when an AI-first company uses automation to scale service while protecting the customer relationship. We get practical about the messy middle: migrating long-lived support reporting, pulling data from multiple sour...
Send us Fan Mail 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 Jenny Dempsey hit so hard: she went from a clear leadership path in customer experience to two years of uncertainty, experimenting with consulting, and rebuilding from a place that felt anything but predictable. We talk about the moment...
Send us Fan Mail 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, teams are tempted to retreat into silos, and “insular thinking” makes cross-functional work painfully slow. We dig into what Fearless CX looks like inside the organization: leaders acting as a beacon, building trust through character a...
Send us Fan Mail 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 why the future of support is bigger than faster replies. We talk about how human-first support can still thrive while using AI in customer service in a way that actually improves the customer experience. We dig into the real shift: movin...
Send us Fan Mail 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 “bots are coming for our jobs” narrative misses the most important part: new jobs are being created right now. We dig into what AI chatbots are genuinely good at, like handling simple requests and searching your help center faster than a...
Send us Fan Mail 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 professional identity to seasoned operators who navigate constraints with judgment and calm. Andrew draws on an unexpected source—coaching youth sports—to reveal practical tactics that translate directly to support leadership. We star...
Send us Fan Mail 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 journey to unpack a bigger shift: the changing identity of support as AI handles the basics and reshapes teams, metrics, and roles. Across this candid conversation, we question what “foundations” really mean. If bots resolve simple ticke...
Send us Fan Mail 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 from your busiest dates, define the role around outcomes, and keep a flexible grip on how you staff it. Charlotte welcomes Matt Dale to dig into the details leaders wrestle with every year. We talk through working from your go-live date t...
Send us Fan Mail 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 faster, and pays off across the business. Greg has lived every stage of the customer journey—sales, implementation, and support—so he brings a pragmatic lens to what works. We dig into the two traits that define a true champion—willingn...
Send us Fan Mail 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 blueprint: protect privacy, reduce friction, and design for reliability before anything else. From coordinating restaurant bookings across phone, SMS, WhatsApp, and email to safeguarding patient pathways where there’s no “fix it later,” ...
Send us Fan Mail 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 work fast without dropping standards. Matt Dale joins Charlotte Ward to unpack how to keep people safe, outcomes clear, and momentum steady when the plan changes mid-flight. We start with the groundwork that makes speed possible: knowi...
Send us Fan Mail 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 refunds, detect spam, and personalize replies across channels. The core shift is mindset: once software handles tasks, you need to manage it like a teammate—measure output, audit quality, plan capacity, and set honest expectations about...
Send us Fan Mail 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 can design for consistency without losing the human judgment that creates loyalty. Ty shares the evolution from rigid scripts to flexible playbooks that teach thinking. We explore the 80/20 guardrails that keep quality high while giving ...
Send us Fan Mail 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, the leadership ladder compressing, and the customer journey turning truly dynamic. With Alec back on the mic, we share what sparked our collaboration, why the site overhaul mattered, and how we’re structuring episodes to turn complex t...
Send us Fan Mail 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 consultant Conor Pendergrast, we unpack why a perfect plan won’t move the needle without the conditions that make good choices easy under pressure. We start by drawing a clean line between objectives, strategy, and tactics—then flip t...
Send us Fan Mail 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 momentum. Charlotte sits down with customer and employee experience strategist Marc Haine to unpack a practical toolkit that works across hospitality, retail, government services, and B2B support. We start with a simple truth: your firs...
Send us Fan Mail 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 for support. He was recognized as an Innovator by the Consortium for Service Innovation, and has been KCS v6 Certified as a Knowledge-Centered Service (KCS) practitioner, coach, and trainer. He held leadership roles at an innovative knowledge management technology provider from e...
Send us Fan Mail 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 must be a core stakeholder, how trust and blamelessness turn heat into focus, and the small operational moves that make the next incident smoother than the last. We start with the why: customers feel the wobble first, and support carri...
Send us Fan Mail 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 difference between toy and tool, sharing lessons from building conversational analytics and automated QA across diverse industries. We dig into the myth of “one model to rule them all” and get specific about task fit. Generative models shine at...
Send us Fan Mail The alarms stop, but the real work is just getting started. Charlotte Ward and Kat Gaines pull back the curtain on what effective teams do after an incident is resolved—how to pause, learn, and communicate in a way that actually strengthens trust. We explore why a short breather prevents knee‑jerk conclusions, how to balance pressure for instant answers with thoughtful analysis, and what belongs in a preliminary update versus a full review. Kat explains how to structure a li...
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