Live Chat with Jen Weaver – Details, episodes & analysis

Ever feel like your to-do list is calling the shots? Elyse Mankin has been there, and she figured out how to take back control.

As Head of Support at Attio, Elyse knows firsthand how hard it is to shift from individual contributor to team lead without drowning in tasks. In this episode, she gets real about the habits that don’t scale, the ones that do, and what it takes to rebuild your time management from the ground up.

We get into the messy (but rewarding) process of spotting your own pitfalls, building a planning rhythm that sticks, and coaching your team to find their own flow, instead of just copying yours.

Here’s what we dig into:

• Why the move from IC to manager breaks your old time habits
• How Elyse sets a yearly-to-daily cadence to stay focused
• Her go-to frameworks for prioritizing (Rule of 3 + Eisenhower Matrix)
• How to coach time management without micromanaging

Whether you're scaling a team or just trying to tame your own calendar, this episode gives you a toolkit (and mindset) for leading with clarity and care.

Keep Exploring:

📬 Subscribe for weekly tactical tips → Get Weekly Tactical CX and Support Ops Tips

🔍 More of Elyse’s insights → Elyse Mankin on LinkedIn

🎙 Keep listening → More Episodes of Live Chat with Jen Weaver

🗣 Follow Jen for more CX conversations →Jen Weaver on LinkedIn 

 🤖 Sponsored by Supportman: https://supportman.io

Let’s face it, support roles don’t always get the credit they deserve. Too often, people see them as just a pit stop on the road to something “better.” But what if it could be both a launchpad and a place worth landing?

In this episode, I talk with Alex Plasket, one of those rare leaders who makes people want to stay. His team isn’t just high-performing; they genuinely like being there. And it’s not because of secret handshakes or group tattoos (although, that’d be iconic). It’s because Alex builds culture from the inside out, starting with trust.  

We’ll delve into his best practices for building high-retention, high-trust support teams. You’ll learn:

• How to structure onboarding so it saves time in the long run.
• Alex’s “problem vs concern” framework (I want him to write a book on this!).
• The power of coaching with real conversations, not generic modules.  
• Ways to spot career growth opportunities before they’re even asked for.  

Maybe you’re working on making onboarding less of a headache, or you’re trying to hang onto great people, or maybe you just want to help your team move up. Whatever the case, Alex offers a refreshingly real and useful approach to leading in support.

If you’re building a team and want it to feel more like a landing pad than a revolving door, this episode is for you.

Your Next Moves:

📧 Join the newsletter: https://live-chat-with-jen.beehiiv.com/ 

🔗 Follow Alex on LinkedIn: https://www.linkedin.com/in/alex-plasket/ 

👩‍💻 Connect with Jen: https://www.linkedin.com/in/jen-weaver/ 

🤖 Sponsored by Supportman: https://supportman.io

Episode Time Stamps:

00:00 – Welcome + why trust matters

04:13 – Team success  starts with hiring

11:10 – Cue walkthroughs to help you scale

14:00 – Lost card ticket coaching example

18:00 – Ticket QA after onboarding

23:55 – Finding teachable moments

30:00 – Important vs urgent

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-changing solution
✅ The exact steps she took to implement sprints for her team
✅ How she used ChatGPT and Slack Lists to refine and track their process
✅ The surprising insights that helped them shift from 1:1 meetings to scalable customer education
✅ How sprint retros helped them continuously improve and optimize CX

This episode is packed with even more resources than any of our other episodes: visit our resource hub for meeting notes, Steph's playbook, and her repeatable project plan.

And subscribe to our email newsletter to get access to the full library of resources from every episode!

🎧 Hit play and learn how to bring Agile thinking to your CX team!

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.

🎥 Watch on YouTube 

📑 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 Introduction to Customer Support Leadership
00:08 The Startup Environment and Its Challenges
01:44 Understanding the Customer Journey
03:09 Building Effective Processes from Scratch
05:04 Setting Up a Support System
06:25 Creating a Knowledge Base
07:00 Utilizing AI in Customer Support
07:39 Feedback Loops and Customer Engagement
08:03 Scaling the Support Team
08:23 Preparing for Future Growth
09:50 The Importance of Communication
10:58 Planning for Absences and Documentation
14:36 Building Strong Customer Relationships
16:11 The Role of Customer Feedback in Product Management
18:15 Automating Customer Support Processes
20:59 Transforming Customer Support into a Revenue Generator
22:25 Maintaining Documentation and Processes
24:18 The Importance of Community and Networking

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 exact tools Rob used to streamline workflows
✅ How non-coders can start automating with AI-generated scripts
✅ Why automation isn’t about replacing people—it’s about freeing them up for higher-value work

🚀 Listen now and start automating!

 📩 Get weekly tactical CX & support ops tips → https://live-chat-with-jen.beehiiv.com/
🔗 More episodes of Live Chat with Jen Weaver → https://www.buzzsprout.com/2433498
📑 Download Rob's automation template and playbook here → https://drive.google.com/drive/folders/1o9cPleC3alW3AV4rZc83V-M5F8ajsum0?usp=sharing

Sponsored by Supportman.io

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 streamlined the transfer of heated conversations to leadership.
• Psychological Safety First: Why protecting frontline agents from abusive interactions is essential for team well-being.
• Manual Escalation Done Right: When and how support agents should escalate challenging conversations.
• Leadership Accountability: The surprising benefits of having senior leaders engage directly with customers.
• Practical Tips: How you can implement a similar escalation process, whether you’re using Help Scout, Zendesk, or Intercom.

Of course we want you to listen to this insightful episode packed with strategies you can implement today, but also you can get Conor's playbook here.

And get all our playbooks by subscribing to our email newsletter! ➡️ tettra.beehiiv.com/subscribe

If that's not enough goodness for you, subscribe to Conor's newsletter for tons of useful CX content! ➡️ www.customersuccess.cx/newsletter

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 uses tools like Asana, Guru, and TextExpander to create scalable processes, anticipate customer needs, and empower her team to handle any release with confidence. Whether you're in customer support or product enablement, this episode is packed with actionable insights to help your team thrive.

🎧 Subscribe to our newsletter now: https://live-chat-with-jen.beehiiv.com

We'll send you a link to download our free step-by-step playbook with Ashley’s templates and tips!

#CustomerSupport #ProductEnablement #SaaS #ProductReleases

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 journey maps to developing content strategies.

Creating a Customer Journey Map with AI: Meg walked us through her process of feeding ideas into AI, refining outputs, and creating a visual customer journey map in just 15 minutes—a task that might have taken hours otherwise.

AI as a Collaborative Partner: Meg uses AI iteratively—adjusting prompts and refining outputs until the results align with her needs.

Featured Tools:

• Claude by Anthropic: Streamline customer journey mapping and other workflows.
• ChatGPT: Your go-to tool for brainstorming, drafting, and productivity hacks.
• Intercom, HubSpot, Calendly, and Notion: Tools Meg recommends for startups building their tech stack.

Communities Mentioned:

• Support Driven: A free community for customer support professionals.
• Elevate: A community to connect and grow in customer success.

Jen’s Closing Thoughts:

This episode underscores the transformative power of AI in modern workflows, especially in startup environments where time and resources are limited. Whether you’re drafting a customer journey map or building a content strategy, AI can help you work smarter, not harder.

Subscribe & Share:

If you enjoyed this episode, don’t forget to subscribe, rate, and review! Your support helps us bring more actionable insights to professionals like you.

✨ Let’s keep the conversation going—reach out with your challenges, and we’ll find an expert to help solve them!

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 the noise. 

Craig’s back to break down a real-world approach to using AI in support, with actual processes he’s refined over time. He even brings receipts, like the time AI caught a spike in… rotten sweet potatoes. 

If you’re wondering where to start with AI or how to make sure it’s doing what you hired it for, this one will save you hours of trial and error.

🔧 Sponsored by Supportman.io, linking Intercom to Slack for instant, made-for-you ticket QA.

You'll learn:

• A “crawl, walk, run” approach to AI that support teams can actually follow
• How to clean and connect your support data across platforms like Intercom, Pendo, and your CRM
• What to define before buying an AI tool and how to avoid mismatched solutions
• Real-life examples of how AI can detect trends before humans do (yes, even rotten sweet potatoes)

Your Next Moves:

📧 Join the newsletter: https://live-chat-with-jen.beehiiv.com/ 

🔗 Try Craig’s Erlang Calculator: https://stoss.ca/erlang-model-calculator 

📌 Learn more about Craig: https://stoss.ca 

👩‍💻 Connect with Jen: https://www.linkedin.com/in/jen-weaver/ 

🤖 Sponsored by Supportman: https://supportman.io

Timestamps:

00:00 Intro

01:20 The Exercise Bike Problem

03:20 Connecting the Dots Between Tools

08:30 The Purist vs. the Realist on Customer Feedback

10:15 Can AI Really Filter the Noise? “Bs and 3s”

15:30 Known vs. Unknown: Two Ways to Use AI Analytics

22:30 Crawl, Walk, Run: How to Start with AI in Support

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-select fields cause more harm than good, how to figure out what metrics are worth tracking, and how AI tools are making clean data easier to access. If you’ve ever stared at a report and thought, “What am I even supposed to do with this?” you’re not alone. This episode will help you reset your approach and focus on what actually moves the needle.

🔧 Sponsored by Supportman.io, linking Intercom to Slack for instant, made-for-you ticket QA.

You’ll Learn:

• The two biggest data mistakes support teams make (and how to avoid them).
• Why single-select fields and rigid data structures kill your reporting.
• How to approach capacity planning without overcomplicating it.
• The two exact metrics you need to start capacity planning today.
• Why migrating all your old data to a new system probably isn’t worth it.
• How AI is Transforming Data Reporting and Why Rigid Categories Are Becoming Obsolete.

Timestamps:
 00:00 – Intro
 01:45 – The Biggest Data Mistakes Support Teams Make
 08:30 – Why You’re Overcomplicating Capacity Planning
 15:40 – The Only Two Metrics You Really Need
 22:10 – How AI Is Changing Support Reporting
 30:00 – What Data to Keep, What to Throw Away
 35:50 – Final Advice for Support Leaders

Your Next Moves:

📧 Join the newsletter: https://live-chat-with-jen.beehiiv.com/ 

🔗 Try Craig’s Erlang Calculator: https://stoss.ca/erlang-model-calculator 

📌 Learn more about Craig: https://stoss.ca 

👩‍💻 Connect with Jen: https://www.linkedin.com/in/jen-weaver/ 

🤖 Sponsored by Supportman: https://supportman.io