Customer Support Leaders

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 se...

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 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...

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 th...

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 in...

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...

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 p...

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...

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 i...

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 pla...

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 co...

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...

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 ho...

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 traine...

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 s...

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...

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, a...

Send us Fan Mail Ever wondered what distinguishes a true leader from the rest? Join me, Charlotte Ward, as I unlock the secrets of leadership potential within customer support teams alongside Meredith Malloy. Discover how to identify the "unicorns" among your team—those rare individuals who possess the natural empathy and connection skills that are foundational to effective leadership. M...

Send us Fan Mail Unlock the secrets to mastering technical support as we, Robert Cabral and I, guide you through the art of enlisting engineering support for complex inquiries. You'll discover how data-driven strategies can transform your support processes, leading to a drastic reduction in ticket escalations. Robert shares his expertise on creating a robust taxonomy for categorizing issues,...

Send us Fan Mail Unlock the secrets to building a standout customer support team by tuning into our captivating conversation with Alyssa Purcell, a seasoned manager from New York City. Alyssa brings her expertise to the table, offering strategies for crafting precise job descriptions that attract the right candidates. She shares the nuanced art of balancing skills assessment with cultural fit, and...

Send us Fan Mail Unlock the secrets to mastering incident management with our latest episode featuring the insightful Kat Gaines. Discover how to transform your customer support strategy by crafting effective incident communications and building strong interdepartmental relationships. Learn from Kat as she delves into the complexities of maintaining a unified communication strategy amidst a sea of...

Send us Fan Mail Kristina King returns to the spotlight, sharing her remarkable pivot from finance and teaching to becoming a technical support engineer, all without a formal CS degree. Kristina's narrative underscores the power of varied backgrounds in tech, illustrating her philosophy of hiring for culture "add" rather than culture "fit." She emphasizes the need to exten...

Send us Fan Mail Ever wondered how startups can access top-tier leadership without bringing on full-time executives? Brian Levine , joins me to share his journey and unpacks the innovative concept of fractional leadership in customer support.  Brian has been in tech support, in one capacity or another, for 15 years. He's been VP of Support at GitHub and Head of Support at Plaid, among others....

Send us Fan Mail From The Archives: Careers in Support Discover the secrets of building a thriving career in the customer support industry as Matt Dale joins me to unravel the multitude of paths available for support team members. From nurturing the journey of an individual contributor to embracing leadership roles or exploring new arenas like QA and customer satisfaction, this episode promises to...

Send us Fan Mail What happens when the adrenaline rush of an incident meets the need for effective communication? Join us as we chat with Kat Gaines, the leader of PagerDuty’s developer advocacy and community team, who brings her expertise to the table. You’ll walk away with a clear understanding of how maintaining transparent communication not only soothes nerves during crises but also keeps cust...