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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.
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Send us a text 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 ag...
Send us a text 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 tre...
Send us a text 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 the...
Send us a text 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 first ...
Send us a text 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 ear...
Send us a text 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 carries...
Send us a text 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 q...
Send us a text 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 live...
Send us a text 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. Meredith sheds light on how these talents can transform into impactful leadership roles, enhancing both employ...
Send us a text 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, ensuring clarity and efficiency in resolving them. We promise you'll leave with actionable insights into...
Send us a text 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 the importance of having a diverse interview panel featuring both leadership and peers for a compr...
Send us a text 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 different tools and remote work challenges. We'll walk you through the importance of clearly defin...
Send us a text 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 extend opportunities to those who might not traditionally find their way into tech, particularly through her role on hiring commi...
Send us a text 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. These days he's the co-founder of Yetto, a help desk for modern support teams. Brian lives in Rome ...
Send us a text 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 equip you with the insights to chart your career course. Matt shares an inspiring story of a tea...
Send us a text 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 customer expectations in check. Gain insights into how developing empathy between engineering teams and...
Send us a text Mike Redbord, a seasoned veteran from HubSpot with over a decade of experience, joins us to unravel the mysteries of managing customer support beyond mere numbers. Discover why Michael believes that looking past the spreadsheets can uncover stories of exceptional customer service, and how these anecdotes can act as guiding beacons for your team. He shares valuable insights on balancing data-driven management with the art of storytelling, ensuring that as teams grow, the human e...
Send us a text Discover how to master the delicate art of balancing automation with human interaction in customer support, as Corey Brown and Elliot Fox share their expert insights. Facing the pressure to adopt AI while keeping a personal touch can be challenging for businesses. This episode uncovers the potential pitfalls of over-relying on AI, such as generic responses, and emphasizes the importance of human intervention to ensure customer satisfaction. Listen as we explore how AI can serve...
Send us a text Unlock the secrets behind the spreadsheets and discover the hidden complexities of customer support with me and my special guest Ash Rhodes. Ash brings his seasoned perspective on the pitfalls of reducing support staff to mere numbers, reminding us of the importance of understanding the real-time dedication required to resolve customer issues. Together, we explore the nuances of ticket handling and the dangers of setting unrealistic performance goals. Ash sheds light on the oft...
Send us a text Ever wondered how a support desk manager transforms the reputation of their team from the "black sheep" to a pivotal player in brand development and customer interaction? Join me, Charlotte Ward, as I sit down with Steve Tondé from PayShepherd, a Canadian fintech company, who shares his transformative leadership journey and the evolving role of support teams in today's tech-driven landscape. With the rise of SaaS, support teams are stepping into the spotlight, and Steve shares ...
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