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. 6D AGO

    303: Practically Perfect Support; with Jason Yun

    Send us Fan Mail 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 translate timeless ideas into practical support team lessons: hire for kindness and wit, stay close to the frontline, and remember that people at work still want to be seen, heard, and understood even when the market feels harsher than it did a few years ago.  We talk about advocacy and allyship through “Sister Suffragette”, and we confront the Mr Banks trap: getting rigid, comfortable, and oblivious while chaos quietly builds around you. From there we get extremely tactical with “A Spoonful of Sugar”, unpacking how support leaders deliver bad news, write appeasement emails, de escalate tense calls, and keep dignity intact for customers and agents. We also call out the gap between big vendor visions and what teams actually need day to day, including an honest take on AI in customer support and why hype rarely matches real budgets or proven outcomes.  Along the way, Bert becomes the model for a different kind of leadership voice: the storyteller who reframes, suggests alternatives, and helps people change without being shamed. We close with “Let’s Go Fly A Kite” and a simple north star for the future of customer success and customer support: let automation handle the boring clicks while humans lead with trust, relationship building, and product insight that actually improves the customer experience. If this made you rethink your own leadership style, subscribe, share the episode with a fellow support leader, and leave a review. Support the show

    1h 9m

  2. MAY 13

    302: Using AI to identify coaching opportunities; with Rob Dwyer

    Send us Fan Mail 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, like unclear expectation setting or a pattern that repeats across channels. I’m joined by Rob Dwyer, Senior Technical Account Manager at Level AI and CX Executive in Residence, to unpack how AI can identify coaching opportunities without pretending to replace leadership. We use a surprisingly useful golf analogy to explain the core problem: agents are “playing” all day long, on different levels of difficulty, while supervisors are juggling escalations, PTO, reporting, and intraday chaos. In that reality, humans cannot reliably watch enough work to spot true patterns, but AI can, because pattern recognition is exactly what these models do well. We also get practical about what “signals” can look like, including an omnichannel example where an agent sounds fantastic on the phone but struggles with written communication in email and ticket replies. That’s a hidden coaching gap unless you’re analysing conversations across voice and async work. Along the way, we talk about using AI to highlight strengths so recognition is specific, and how this can help newly promoted managers calibrate quickly between foundational coaching and skill refinement. If you want coaching that feels fair, evidence-based, and actually improves customer experience, listen now, then subscribe, share this with a fellow support leader, and leave a review with the biggest coaching blind spot you see on your team. Support the show

    37 min

  3. MAY 6

    301: Using AI To Make Us Better Managers; with Reagan Helms

    Send us Fan Mail 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 strengthens one-on-ones without turning leadership into autopilot. We get specific about how Reagan built his system and how it evolved, from separate AI chats per employee to a persistent copilot that can pull the right notes at the right time. We talk about the real-world plumbing behind “AI for managers” including Notion as a human-friendly interface, why Notion can be painful as a retrieval layer, when spreadsheets are the simplest high-performance backbone, and how a vector database can unlock faster search across qualitative coaching history. We also dig into meeting transcription, prompt refinement, and the discipline of verifying outputs so the manager stays responsible for the data and the decisions. Then we zoom out to the leadership impact: fuller agendas, fewer forgotten commitments, and an “impartial mirror” that helps you sanity-check whether you communicated clearly or whether an annoying behaviour is actually your coaching taking root. We also tackle the trust side head-on, with boundaries and consent so AI support doesn’t drift into surveillance or creep your team out. If you’re leading customer support, customer experience, or any growing team, hit play, share it with another manager, and subscribe for more. After you listen, leave a review and tell us: what would you want an AI management assistant to handle first? Support the show

    39 min

  4. APR 29

    300: Reflecting on the Year So Far; with Alec Moloney

    Send us Fan Mail 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 faster tooling collide with the day-to-day reality of customers, tickets, and people management. We get practical about the new build vs buy trade-offs for AI in customer service. Alec shares what it looks like to evaluate vendor platforms and aim to shift a meaningful chunk of ticket volume to AI-assisted chat and email, while Charlotte explains why her instinct is often to build custom systems that fit the exact workflow. Along the way we talk Zendesk reporting, scripts generated with AI, and why “solve the problem in front of you” has become a useful operating principle for support operations and CX leadership. Then we zoom out to the bigger changes: blurred boundaries between support, ops, and adjacent functions, the need for centralised knowledge (Notion, Confluence, knowledge bases) to make AI effective, and the weird new shape of career progression. Title compression and flatter orgs mean growth can feel like more scope and more influence rather than a clean promotion, which raises real questions about sustainability, delegation, and what different team members actually want from their careers. If you lead customer support, CX, or support ops and you are trying to make AI useful without losing the human layer, this conversation will give you language, examples, and a few sharp edges to think about. Subscribe, share this with a fellow support leader, and leave a review with the one change you are seeing most in your own team. Support the show

    59 min

  5. APR 22

    299: AI Won't Fix Your Knowledge Quality Problem - It'll Expose It; with Leslie O’Flahaven

    Send us Fan Mail 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 customer support leaders and knowledge management teams: AI won’t fix your knowledge quality problem, it will expose it. We get practical about what AI can do well (drafting, simplifying language, reformatting for different audiences) and what it cannot do for you (understanding the real human reader who is stressed, new to the task, or missing context). Leslie explains why writing is more than editing and why relying only on revision can create “brain flab” as teams stop practising planning and organising. We also dig into a better way to judge content: stop asking users whether they like it and start asking whether they can complete the task with your self service help. From there, we explore concrete tactics to make the reader real again: using daily ticket feedback as gold, building articles around customer questions, and designing knowledge base and FAQ structure that works for both humans and AI search. If you’re feeling AI fatigue, this conversation reframes the moment as an opportunity to do more meaningful knowledge gardening, not less. Subscribe for more conversations on support leadership, AI in customer service, and knowledge base strategy, and if this helps, share it with a teammate and leave a quick review. Support the show

    43 min

  6. APR 15

    298: Returning to the Office; with Andrew Rios

    Send us Fan Mail 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 years of remote work, and what it takes to make that shift sustainable for customer support leaders running busy teams. We dig into the practical mechanics that decide whether office life works: owning your calendar from day one, carrying over non negotiables like school runs and family time, and factoring in commute time so your week doesn’t silently stretch. Andrew shares how he protects evenings over the long haul even in a role where outages and service interruptions can happen, and why it can take time to build the right rules of engagement. Then we get into the hard part: getting work done when people can see you. We talk deep work blocks, the hidden cost of context switching, and how “Do you have a minute?” can derail an entire morning. Andrew explains how he sets office norms, sometimes even stepping into a coffee shop to recreate a remote focus setup, and how he turns walk up escalations into coaching moments that build team autonomy over time. If you’re navigating return to office, hybrid work, or simply trying to protect focus and work life balance in a contact center or support environment, this one is packed with tactics you can use immediately. Subscribe for more practical customer support leadership conversations, share this with a leader who’s struggling with office interruptions, and leave a review with your best calendar boundary. Support the show

    27 min

  7. APR 8

    297: AI Beyond The Queue; with Robert Cabral

    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 sources, and turning scattered metrics into a clear weekly narrative that product and leadership can actually act on. Robert shares how AI helps teams find the story inside ticket data, platform usage, and escalations, and why reporting is only valuable when it drives a better customer experience, a better product roadmap, and a better day-to-day for the support team. Then we move past talk and into action. We discuss chatbot foundations for product education, plus higher-impact automations that do real work, like refund handling with strict guardrails and human escalation when context is missing. We also explore how AI enables support teams to build internal tools and repeatable templates, even without traditional engineering backgrounds, and why that capability can become a career accelerator across CX, product, QA, and engineering. We close on leadership: how to address the fear that AI will replace support roles, how to set customer-focused goals, and how to plan for different outcomes if AI resolves 90% of questions or falls short. If you care about customer support AI, CX automation, AI reporting, and building durable teams in a fast-changing landscape, you’ll want this one. Subscribe, share with a fellow support leader, and leave a review if it helps you rethink your AI roadmap. Support the show

    33 min

  8. APR 1

    296: Flipping Away From Leadership; with Jenny Dempsey

    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 she realized a leadership title no longer matched her values. Jenny shares what it was like to apply for individual contributor roles with 20 years of experience, get judged as “overqualified,” and wrestle with the temptation to downplay her background just to get hired. We also unpack a healthier approach: owning the choice, leading without the org-chart label, and focusing on skills that actually create impact like clear communication, customer empathy, and making work easier for the team. Then we zoom out to the unexpected parallel that ties it all together: her furniture flipping business. The product is different, but the customer journey is the same. Setting expectations, choosing the right channel, giving progress updates, and protecting trust when timelines are long. Charlotte puts it simply: silence kills trust. If you’re navigating layoffs, a career pivot, burnout, or a non-linear support career path, you’ll leave with practical mindset shifts and a better way to tell your story. Subscribe for more real conversations about customer support careers, share this with a friend who’s rethinking their next move, and leave a review with the title you’re ready to stop chasing. Support the show

    36 min
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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
    366
  • Rating
    Clean
  • Copyright
    © 2026 Customer Support Leaders
  • Show Website
    Customer Support Leaders