Customer Support Leaders – Details, episodes & analysis
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Customer Support Leaders
Charlotte Ward
Frequency: 1 episode/6d. Total Eps: 360
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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See allScore global : 48%
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297: AI Beyond The Queue; with Robert Cabral
mercredi 8 avril 2026 • Duration 33:06
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.
296: Flipping Away From Leadership; with Jenny Dempsey
mercredi 1 avril 2026 • Duration 36:20
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.
287: Extreme Delegation: How To Lead When Everything Changes At 4 PM On An Idle Tuesday; with Matt Dale
mercredi 28 janvier 2026 • Duration 47:12
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: knowing your people, tools, and data; modeling calm, context-rich communication; and showing your work so others can replicate decisions. From there, we move into the safety contract that empowers new owners—explicit boundaries, time-boxed expectations, clear escalation paths, and a promise of advocacy when scope creeps or politics intrude. It’s still your accountability, and staying close with tight check-ins preserves agency while preventing drift.
Then we tackle ruthless prioritization. You can’t hand over your entire mental map and hope for the same outcome. Strip to essentials: customer promises that won’t bend, survival metrics, and the smallest system that delivers them. Pause nice-to-haves, and make smart, short-term investments—like an AI co-pilot or tighter knowledge flows—that shrink ramp time and amplify output. Real stories bring it to life: navigating a six-month secondment during acquisitions, replacing a leader mid-crunch, and accelerating an AI rollout to support hiring and scale.
This conversation is for support and CX leaders who have earned the reputation for getting it done and want a cleaner, calmer way to do it when chaos hits. You’ll leave with scripts, structures, and mindset shifts that turn a blindsiding week into a clear plan with confident owners. If this helped, follow the show, share it with a teammate who’s under pressure, and leave a review with your best extreme delegation tip.
226: 99 Weeks Done
samedi 4 décembre 2021 • Duration 40:43
Week 99 Topic: Reflecting
Looking back over some of the best advice, and a couple of bonus outtakes from the last 99 weeks of the podcast!
Week 100 Teaser
vendredi 26 novembre 2021 • Duration 03:34
From The Archives: Ep 150: Fireside with Mo McKibbin
vendredi 19 novembre 2021 • Duration 36:17
From The Archives: Fireside with Mo McKibbin
Mo McKibbin talks about the challenges of screening for those magical unicorns: technical, customer success-support hybrids, remote, in Europe, ideally with specific industry experience. And we excitedly steal each others' favourite interview questions.
From The Archives: Ep 146: Fireside with Tue Søttrup
vendredi 12 novembre 2021 • Duration 21:26
From The Archives: Fireside with Tue Søttrup
Tue Søttrup helps me kick off this new Fireside season with a conversation about Product-Led Customer Success, and how Dixa have used this approach to drive product engagement and business improvements for the customers at the same time.
From The Archives: Ep 142: Diversity and Inclusion with Antonio King
vendredi 5 novembre 2021 • Duration 16:04
From The Archives: Diversity and Inclusion
Antonio King joins me to talk about the importance of keeping the conversations going, no matter how uncomfortable it feels..
From The Archives: Ep 140: Scary Support Stories with Todd Curtis
vendredi 29 octobre 2021 • Duration 27:10
From The Archives: Scary Support Stories
Todd Curtis tells the scary story that inspired this whole week of terrible tales. I heard this at a conference two years ago and it still gives me chills.
From The Archives: Ep 136: Scary Support Stories with Matt Dale
vendredi 22 octobre 2021 • Duration 09:15
From The Archives: Scary Support Stories
Matt Dale joins me to tell the story of a possessed laptop. And I have rather too much fun with sound effects.
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