Customer Support Leaders

Charlotte Ward
  • 5.0 (2)
  • MANAGEMENT
  • UPDATED BIWEEKLY

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.

  1. MAR 25

    295: Fearless CX; with Nate Brown

    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 and conviction, and creating psychological safety without drifting into comfort or inertia. The goal is healthy tension where people can challenge ideas, learn fast, and collaborate across the enterprise to produce a consistent customer experience outcome. Then we get tactical about modern voice of customer strategy. Nate explains “wild sentiment” the unstructured feedback living on Reddit, YouTube, third-party communities, and public reviews. We talk about how AI search is changing customer support behavior, why customers often solve problems without ever contacting the brand, and how AI-enabled customer experience management platforms can finally harmonize structured and unstructured feedback into real themes, tags, and actionable insights. If you want a customer experience strategy that survives uncertainty and actually earns trust, press play. Subscribe, share this with a CX or support leader, and leave a review, then tell me: where do you think your customers are shaping your brand story today? Support the show

    35 min

  2. MAR 18

    294: What Support Does When AI Takes The Tickets; with Ryan Klausner

    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: moving from reactive ticket handling to proactive support that prevents issues before they hit. That means treating support as a central intelligence function, using AI to surface friction in the customer journey, spotting trends early, and turning messy contact data into clear insights that product and marketing teams can act on. We also get honest about the cultural and coaching work required to help frontline teams become strategic operators, not just great responders. Ryan shares what new roles and skills are emerging, from conversational analysis and prompt design to owning knowledge bases, self-service, and customer education. We also unpack trust, why “fake empathy” from bots can backfire, and how to build a better resolution path with smart escalation and truly white glove human help for complex scenarios. If you’re thinking about customer support careers, CX strategy, or AI driven customer experience, this one will sharpen your view of what’s next. If this conversation helps, subscribe, share it with a support leader on your team, and leave a review with your biggest takeaway. What part of support would you automate first, and what would you protect for humans? Support the show

    23 min

  3. MAR 11

    293: Roles AI is Creating in Support; with Hilary Dudek

    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 any human can, and where they still struggle, especially around empathy, reassurance, and messy edge cases. We also talk about the shift away from chatbots masquerading as humans and toward clearer, more transparent bot experiences that set expectations and make handoffs to human support feel natural. From there we go deep on the emerging roles: AI Support Engineer, support architect, and the growing need for people who can manage connectors across documentation, Slack, email, CRM, and data warehouses. We cover prompt engineering, knowledge management, routing and triage, hallucination risk, and why sensitive areas like billing and legal context still require careful human oversight. Hilary also shares a practical example of rapid experimentation: building a “support psychic” with AI that predicts likely follow-up questions and suggested responses from recent ticket patterns. If you lead support operations, manage customer experience, or you’re on the frontline wondering how to stay relevant, this conversation is a roadmap for leaning in with confidence. Subscribe, share this with your team, and leave a review, then tell me: what AI-powered support role do you want to see next? Support the show

    30 min

  4. MAR 4

    292: Tailoring Your Coaching as People Grow; with Andrew Rios

    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 start with the early-career stage, where strong opinions and limited exposure often collide. Andrew’s approach is simple and effective: observe first, set clear expectations, explain the why, and check for understanding without condescension. He shares how to model the behavior you want, turn feedback into co-created next steps, and transform “I’m right” energy into team-first outcomes. Along the way, we talk about relatable storytelling, sticky lessons, and the value of asking people to reflect back what they heard so alignment sticks beyond the meeting. As the conversation moves to senior ICs and emerging leaders, we shift to the realities of budgets, staffing, and process limits. Here, coaching is less about task accuracy and more about decision quality, trade-offs, and influence without authority. Andrew explains how transparency builds trust, how to run adult reflection loops (“If you could do it again, what changes?”), and why change usually takes longer than a 90-day plan. We also dig into inheriting teams, decoding norms from past workplaces, and preventing message drift by re-anchoring the why at regular intervals—even with your top performers. Throughout, vulnerability is the backbone. Andrew talks openly about owning mistakes on the field and at work, thanking the team for the save, and using those moments to strengthen culture. If you’re a support leader, manager, or senior IC looking to evolve your coaching playbook, this conversation offers concrete tools and a mindset shift: meet people where they are, coach for where they want to go, and resist coaching them where they don’t. If this resonated, follow the show, share it with a fellow leader, and leave a quick review to help more people find these conversations. Support the show

    30 min

  5. FEB 25

    291: The Changing Identity of Support; with Lauren Eimers

    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 tickets in seconds, where do managers, directors, and VPs create value? We argue the center of gravity moves toward experience design: setting tone, training AI with the right knowledge, defining escalation paths, and architecting journeys that leave customers feeling seen and confident. That is where human strengths become strategy—storytelling that builds trust, empathy that defuses tense moments, and ethical judgment when answers affect health, money, or safety. We also get practical about fear and planning. Instead of waiting for clarity, we model scenario thinking: inventory your durable skills, map them to AI-augmented roles like knowledge architecture, prompt strategy, and quality review, and use community to test and refine your plan. Expect a nonlinear path—more lily pads than highways—and treat each step as a chance to strengthen the human elements machines can’t replicate. The pace of change is fast, but the purpose endures: create support that feels simple, respectful, and human, even when the system behind it becomes radically new. If this resonates, follow the show, share with a teammate, and leave a review telling us which human skill you plan to double down on next. Support the show

    33 min

  6. FEB 18

    290: From Timelines To Fit: Making Smart Support Hires; with Matt Dale

    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 to set posting windows, ramp time, and notice periods, then pressure-test those assumptions against service level goals and budget. Matt shares hard-won lessons on when to hire cohorts for frontline coverage and when a so-called “unicorn” role should be split into two focused positions. We get candid about the risks of fear-based hiring, how to establish contingency plans before you need them, and why automation and AI rarely deliver instant headcount relief. Interviews, we argue, are more first date than crystal ball. Consistent loops and clear rubrics matter, but so does accepting uncertainty and raising the bar for mutual fit. We highlight the power of candidate questions—what they ask reveals how they think—and offer specifics to encourage better two-way conversations. Along the way, you’ll hear strategies for aligning with finance on headcount versus service levels, using contractors to build foundations, and resetting a search when the market tells you your role is mis-scoped. If you’re hiring for customer support or customer experience this year, this conversation gives you a framework to time your postings, avoid settling, and build a resilient team prepared for the real workload, not the wishful slide. Subscribe, share this with a fellow support leader, and leave a review with your top hiring tip—what’s the question you always ask to gauge fit? Support the show

    25 min

  7. FEB 11

    289: Cultivating Customer Champions; with Greg Skirving

    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—willingness and capability—and the concrete practices that build both: targeted training, version discipline, spare and hot-swappable parts, and clear runbooks. You’ll hear how Greg’s “Our Most Successful Customers Do This” handoff reframes expectations, sets troubleshooting ground rules early, and empowers customers to handle tier one and two issues confidently. We also talk about the signals champions surface for customer success and product: emerging use cases, recurring failure modes, and real-world constraints that drive smarter roadmaps. Expect a candid look at metrics, too. When champions grow, ticket volume falls while complexity rises—TTR can increase even as overall outcomes improve. Learn how to tell that story to your leadership and why it matters in an AI-augmented queue. If you want fewer how-to tickets, faster resolution on the hard stuff, and a stronger renewal story, this conversation is your playbook. Subscribe, share with your team, and leave a review with your best champion win or question—we’ll feature our favorites in a future episode. Support the show

    27 min

  8. FEB 4

    288: Support in a High-Trust Environment; with Simone Secci

    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,” the conversation drills into how we plan, measure, and communicate when the stakes are high. We break down layered SLAs that go far beyond first response time, including vendor response targets and customer wait time, and show how each micro‑commitment ladders up to trust. You’ll hear how we centralize multi‑channel communications for quality review, why “fast” isn’t always smart in healthcare, and how scientific rigor steers product choices—down to naming a feature without triggering clinical confusion. When providers are serving vulnerable people and billionaires are operating on tight schedules, the common reality is that no one has time to give perfect reproduction steps. That puts the burden on support to replicate issues, bridge technical and domain language, and escalate with clean evidence. What emerges is a practical playbook for high‑trust support: kill silos, share a language with your users, validate terminology, and align support, product, QA, and engineering around proactive reliability. We talk about onboarding that actually reduces effort, concise walkthroughs that save attention, and the humility to slow down early so sessions, trips, and outcomes don’t fail later. If you lead customer support, success, or product in any high‑stakes space, this deep dive will sharpen how you measure, message, and deliver. If this resonated, follow the show, share it with a teammate, and leave a quick review—what’s one place your team could slow down now to move faster later? Support the show

    34 min
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5
out of 5
2 Ratings

About

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.

Information

  • Creator
    Charlotte Ward
  • Years Active
    2019 - 2026
  • Episodes
    360
  • Rating
    Clean
  • Copyright
    © 2026 Customer Support Leaders
  • Show Website
    Customer Support Leaders

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