The Supportive Podcast

Should you trust a chatbot when it sometimes makes mistakes? Javier Silverio has spent eight years in the Help Scout support queue, and now builds the team's internal AI tools. He read Mat Patterson's Supportive Weekly newsletter on AI and trust, and they get into what it means to hand your data to a company when you can't check what happens to it, why customers have been so quick to forgive a wro...

Dave Berner is a software engineer who, as a two-time founder considers himself "almost unemployable". Dave chats with Mat about careers in an AI-disrupted world. Dave chats with Mat about using AI as a sounding board, keeping people in the loop, and how he thinks about career planning when so much of the future remains uncertain. Watch the full interview here or subscribe to The Supportive in you...

Nicole Crayne, self-proclaimed "Chaos Wrangler" at Saffire, spent 12 years between support roles wrangling the chaos and the curiosity of kids as a stay-at-home parent. Now back in the corporate world, Nicole chats with Mat about what it takes to build curiosity into a team - trust, slack time, and a type of disciplined approach to asking "why". We also learn how her dad has sustained a decades-lo...

Beth Trame has built support organizations from scratch multiple times, including at Lyft and Square, both businesses that dealt with steep volume increases and diverse customer bases. In this episode, Beth shares her experiences as we discuss customer feedback, criticism, and how support teams respond to them. Some key moments (0:19) Meet Beth Trame: Square, Lyft, and 10 years at Google (1:21) Th...

Tom joined Help Scout's support team in 2026, but he's been using Help Scout for a decade. He chats to Mat about his role in improving Zapier's support team diversity, what actually changed to hit their goals, why an interview process that never changes isn't neutral, and how improving diversity also improved camaraderie. Key moments: (5:24) Tom's alottment in the UK, and companion planting as tea...

Thinking about switching help desks? Help Scout support pro Chrissy Chavez tells Mat why the urge to burn it all down and start fresh is so strong — and why an audit should always come first. Chrissy is a senior technical support specialist based in Oahu, Hawaii. She joins Mat to react to his newsletter "Why You Shouldn't Switch to Help Scout" — and the conversation turns into a playbook for anyon...

Pavel drove AI customer support adoption as head of support...and then he got laid off. Mat chats with Pavel about his 13 years in B2B SaaS customer experience about the way execs are thinking about support today. Plus: why customers still want a human to confirm an answer, even when the AI got it exactly right. For a full transcript, notes, and links, see https://www.helpscout.com/blog/inside-ai-...

Leslie O'Flahavan has spent 30 years teaching people to write well at work — including plenty of customer service teams. Leslie and Mat discuss what it takes to write concisely in support, and how to develop your team's concise writing skills. Listen out for Leslie's simple 10% word-count game, and the surprising shift she's made just this year in her approach to spelling and grammar. For full sho...

After 700+ live Help Scout classes, Alison Groves has figured out what makes customer education work — mistakes. Well, not exactly, but that's part of it. In this episode of The Supportive, Mat talks to Help Scout's Customer Education Lead, Alison, about what she's learned, how to get started, and why imperfection builds trust. WHAT WE COVER: - Why 90%+ of Alison's attendees stay for the full sess...

What if making your work visible wasn't about promoting yourself — but about telling the stories of your customers? Help Scout's Kristi Thompson spent nine years on the customer support team. She wasn't angling for a promotion or trying to build a personal brand. She just noticed a gap — consultative conversations that email wasn't suited for — and started volunteering to take those calls. She tra...

Season 2 of The Supportive brought together founders from seven very different businesses — software, hardware, beer, mattresses, and more — all with a reputation for putting customers first. In this wrap-up episode, Mat draws out the five themes that ran through every conversation: being your own customer, staying close as you grow, values that drive real decisions, deliberate growth, and treatin...

Mat sits down with David Sparks — lawyer turned full-time creator — as he shares how 28 years in the courtroom shaped his approach to serving his technology audience. From playing imaginary clown music at raging opposing counsel, to personally answering emails from 93-year-old customers, David reveals what it looks like to build a business around kindness, craft, and staying close to the people yo...

NapLab — Our First Customers on The Supportive Mat Patterson talks with Derek Hales, founder of mattress review site NapLab, about building a customer-centric business in an industry that works hard to keep consumers in the dark. Derek shares how a frustrating mattress shopping experience led him to create one of the web's most rigorous product review platforms — and what happens when the reviews...

Mat sits down with Oscar McMahon, co-founder of Sydney brewery, Young Henrys, as he shares how community, values, and a ‘challenger mindset’ have helped build one of the city's most loved independent companies. From the Inner West music scene to their “Serve the People” ethos, Oscar shares how purpose shows up in hiring, customer service, and business strategy. Full show notes and links: https://w...

Todd Curtis, CEO of YNAB, shares how customer support became the foundation for sustainable growth. Learn why they embedded support in product teams and used it as a training ground for company-wide leadership. Here's the original YNAB Support Ethics document (long since replaced with expanded versions) https://2760806.fs1.hubspotusercontent-na1.net/hubfs/2760806/YNAB%20Support%20Ethic.pdf Discove...

Chris Savage, co-founder and CEO of Wistia, shares how staying in the support inbox for ten years, walking away from a potential major deal with HBO as customer #4, and choosing patience over growth helped their team build a video marketing platform where every product decision starts with understanding customer pain—not just counting feature requests.

Erez Zuckerman, CEO and co-founder of ZSA Technology Labs, shares how a focus on craftsmanship, honest communication internally and externally and deep support has helped his small keyboard company punch well above its weight.

What does it take to earn the trust and loyalty of over 12,000 customers, build a team that cares like you do, and hold onto your values for over a decade? In the first episode of season 2, go behind the scenes with the three founders of Help Scout – Nick Francis, Denny Swindle, and Jared McDaniel – and hear how they turned their frustrations with clunky support tools into a business renowned for...

Mat answers Ita's newsletter-follow-up question: How can we frame AI chatbots as self-service tools, not worse-than-human support? Find the original newsletter here: https://email.helpscout.com/harm-joy and visit https://helpscout.com/blog/blog/reframing-as-chatbots/ for further links. Thanks Ita for the great question!

Season 1 of the podcast comes to an end, and Mat explores the recurring themes in classic clip-show style. Listen for a sneak peek of season 2!

Priscilla Brooke leads a team of support experts to help podcasters run, distribute, and grow their shows. In this episode she talks about her journey into support, and her approach to service at Buzzsprout.

Elevate CX founder Sarah Hatter chats with Mat (again!). This time, she shares her community building journey from idea to impact, revealing how in-person connections, shared wisdom, and a true sense of belonging have shaped Elevate CX into the community it is today. For the full show notes, transcript, and links: https://www.helpscout.com/resources/supportive-podcast/S1E9/

Sarah Hatter — support veteran, community legend, and founder of ElevateCX — joins Mat to talk about the early days of SaaS support, and the human support of the future.

Mat and a bunch of support experts share actionable tips, encouragement, and helpful advice for people new to support, those considering a support career, and even jaded veterans. For show notes, further reading, and links to our contributors, see https://www.helpscout.com/resources/supportive-podcast/S1E7/ A huge thank you to everyone who contributed their wisdom to this episode! Andre Linde, Bla...

In the final Supportive Podcast of the year, Santa's dealing with change, just like the rest of us, and Mat has some thoughts and thanks as we consider 2025.