Live Chat with Jen Weaver
Customer Support QA and Training: I deliver bite-sized episodes every two weeks that each dive into a single solution, showcasing the tech stacks and workflows top support pros use to tackle challenges and optimize their customer and team experience.
Episodes
No matter what industry you're in, everyone’s talking about AI. In support, it’s either the shiny new tool that’s supposed to fix everything or the thing causing confusion, pressure, and a lot of “what now?” moments for team leads.
But what does a realistic AI strategy actually look like? This week on Live Chat with Jen Weaver, I’m joined by Craig Stoss, VP of Partner Solutions at Kodif, for a conversation that cuts through th...
Support teams are swimming in data, but how much of it actually helps you make better decisions?
In this episode, I’m joined by Craig Stoss, VP of Partner Solutions at Kodif, to talk about the two biggest data mistakes support teams keep making and how to fix them. Craig’s been in the CX and support world for over 25 years, and he’s walking us through his 5-step system to simplify metrics.
We get into why rigid dropdowns and single-s...
Have you ever felt like your support dashboard is just a bunch of numbers no one really connects with? In this episode, Jen sits down with Mario Guisado to talk about building dashboards that actually tell a story. Mario walks through his six-step process for making data useful: how to choose the right metrics for the right audience, resonate with your leadership, and build something that supports real change across your organizati...
What actually changes when you become head of support?
In this episode, Jen sits down with Idit Matas—a global support leader with experience at Datadog and Firebolt—to unpack the first 90 days of head-of life. From auditing global coverage and designing on-call rotations, to redefining escalation paths and collaborating cross-functionally, Idit offers a real-world blueprint for scaling support the right way.
If you’re step...
What does it actually take to build a psychologically safe, people-centered support org?
Alex Armstead will share with us 5 solid strategies you can start implementing now. With nearly a decade at Clever (a unicorn in the tech world 🦄) and roots in both teaching and support, Alex shares exactly how they’ve built internal systems that support retention, cross-functional visibility, and real professional growth.
Whether you’re a Suppo...
What do you do when your highest-revenue customers need (and expect) more than your basic support offering?
If you're Miles Goldstein, you create a Premier Support program that delivers real relationships and real retention.
With 20+ years leading global support orgs at B2B SaaS companies, Miles joins our us to unpack how to design and launch a Premier Support offering that actually works—without overwhelming your team or aliena...
What do you do when 1:1 product demos become unsustainable? If you're Alison Groves, you scale—strategically, efficiently, and with a whole lot of heart.
Alison, Customer Education Lead at Help Scout, joins Jen to break down how she turned live classes into a high-converting, one-to-many program. With a background in support and onboarding at places like Zapier, Highrise, and Customer.io, Alison brings 10+ years of experience a...
How do you keep a support team sounding human, helpful, and on-brand as it grows? When scaling, tone drift can turn great support into inconsistent and robotic interactions. Priscilla Brooke, Head of Podcaster Success at Buzzsprout, joins us to share how her team created a Tone Document that ensures every interaction stays clear, friendly, and aligned with their brand.
In this episode, we cover:
✅ How Buzzsprout’s values shaped ...
Steph Hardy, Customer Solutions Engineer at Guru, wanted to become even more efficient with her colleagues—so she borrowed a playbook from engineering and brought Agile sprints to CX.
In this episode, Steph shares how she adapted the sprint framework to fit her team’s workflow, helping them stay focused, reduce redundant work, and increase feature adoption. She walks us through:
✅ How being curious beyond her role led her to a game-c...
Starting as the first (or only) support hire at a growing company? Brittany Ferguson has been there—many times. Instead of feeling overwhelmed, she’s built a process that helps support teams thrive, even when it’s just one person.
📑 Download the step-by-step guide
This podcast is brought to you by Supportman.io, providing instant QA and conversation management from Intercom to Slack.
Chapters
00:00 Introd...
Support teams juggle way too many manual tasks—from sending training invites to formatting reports and tracking progress. But what if you could automate it all with the tools you already have?
In this episode, Rob Dwyer from Happitu shares how he used VBA inside Microsoft tools to eliminate repetitive work, saving hours every week on training, onboarding, and QA.
You’ll learn:
✅ How to identify automation-ready tasks
✅ The e...
I'm delighted to share episode 3 with Conor Pendergrast of CustomerSuccess.cx! In this episode, Conor shares how as the Senior Leader of Customer Success at Expensify, he handled the customer backlash after some contentious executive decisions. We talk about:
- The Turning Point: How Conor identified the need for an escalation process and brought senior leadership into the fold.
- Automation in Action: How keyword flags streamli...
Effortless product launches are possible! In this episode of Live Chat with Jen Weaver, we sit down with Ashley Gutierrez-Seiler from YNAB to uncover her proven strategy for preparing support teams for fast-paced feature releases. As a Product Support Liaison, Ashley bridges the gap between customers and product teams, ensuring smooth communication, up-to-date training, and a seamless customer experience.
Tune in to learn how Ashley...
Connect With Us: Subscribe to get episodes over email!
Meet Meg Palazzolo, a customer success leader with 15 years of experience building and scaling customer-facing teams. Currently at a stealth-mode startup, Meg is using AI to manage multiple hats and streamline workflows in early-stage operations.
AI as a Second Brain: Meg shares how she leverages tools like Claude and ChatGPT for everything from crafting customer journe...
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