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

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 organization.

Whether you're cleaning up a messy reporting system or starting fresh, this conversation will help you create dashboards with purpose and with people in mind.

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

Key Points

• Define a keystone metric and build your story around it
• Differentiate internal coaching data from external leadership reporting
• Test metrics before locking them in
• Build your dashboard after you understand the story
• Avoid common pitfalls like over-reporting or frequent change

Your Next Moves:

💬Follow Mario Guisado on LinkedIn: https://www.linkedin.com/in/mario-guisado/
📬 Get Weekly Tactical CX and Support Ops Tips: https://live-chat-with-jen.beehiiv.com/
🎙️ More Episodes of Live Chat with Jen Weaver: https://www.buzzsprout.com/2433498
👩‍💼 Connect with Jen: https://www.linkedin.com/in/jen-weaver/
🤖 Sponsor Link: https://supportman.io

Episode Time Stamps:

0:00 Intro

1:52 Getting Started - How Mario Landed in Data

3:03 Step 1 - Pick Your Keystone Metrics

8:59 Step 2: Identify Supporting Data

12:44 Step 3: Pressure Test Your Story

17:56 Recap and Step 4: Build a Shareable Format

29:18 Step 5: Watch for Common Pitfalls

32:41 Step 6: Iterate as You Grow

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 stepping into a leadership role or looking to build a healthier, more scalable support function—this is the episode for you.

This podcast is sponsored by Supportman.io, which connects Intercom to Slack and uses AI to give agents feedback and surface problems in real time.

🔍 What You’ll Learn in This Episode

💡 How to audit global coverage based on SLA—not assumptions
💡 Why asking people to work outside of normal hours kills retention
💡 A step-by-step approach to on-call rotation and compensation
💡 Escalation workflows that don’t frustrate engineers or support
💡 How to use AI as a first responder and tie it to human backup
💡 Creating strategic projects that drive revenue and retention

📌 Your Action Kit

👤 Connect with Idit Matas on LinkedIn: https://www.linkedin.com/in/iditmatas/
📬 Get Tactical Support Ops Tips Weekly: Newsletter
🎧 More Episodes of Live Chat with Jen Weaver: Buzzsprout
💼 Follow Jen on LinkedIn: https://www.linkedin.com/in/jen-weaver/
🛠️ Try Supportman: https://supportman.io

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 Support Manager, CX Ops leader, or mid-level IC looking to step into more influence, this episode is a practical guide to people-first growth, without chasing titles or burning out.

🔧 Sponsored by Supportman.io

What You’ll Find in This Episode
💡 Why psychological safety drives better performance
💡How to build meaningful career paths—whether or not they lead to people management
💡The systems that make anonymous feedback actually work
💡Why middle management deserves more resources
💡How to spot (and support) emerging leaders before they get burnt out

📌 Your Action Kit

👤 Connect with Alex Armstead on LinkedIn
📬 Get Weekly Tactical CX and Support Ops Tips 
🎧 Get more episodes of Live Chat with Jen Weaver

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 alienating your customers.

What you’ll find in this episode

💡When (and why) to launch a premium support program

💡The strategy behind dedicated vs designated support roles

💡Why soft skills always win when hiring for premium support roles

💡What systems and tools you must have in place to make it scale

💡When to charge (and how much)

🔧 Check out our sponsor Supportman.io for instant AI quality review in Slack.

🔗 Links & Resources

🤝 Connect with Miles Goldstein on LinkedIn 

📬 Get Weekly Tactical CX and Support Ops Tips: Live Chat Newsletter

🎧 Keep Listening: Find more episodes of Live Chat with Jen Weaver

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 and an incredibly practical approach.

She shares the full blueprint: from tooling and scripting to scaling and training others—plus how she gets measurable results (like 60% trial conversion) while keeping the experience warm and human.

Whether you're building onboarding, demos, or customer education, this episode is packed with real tactics and zero fluff.

🔧 Sponsored by Supportman.io

Key Points
🔑 Why one-to-one demos don’t scale—and how Alison knew it was time to change
🔑 How Help Scout uses Zoom, HubSpot, and Contentful to create a seamless signup-to-class flow
🔑 The exact script + training process that helps her scale classes across teammates
🔑 Tips for running live sessions without burnout—including what to do when you don’t know the answer
🔑 How to measure success beyond just conversions (and why customer feedback matters most)

🔗  Links

 📖Help Scout Blog Post: How We Run Live Classes

📬 Get Weekly Tactical CX and Support Ops Tips: Live Chat Newsletter

🎙️ More Episodes of Live Chat with Jen Weaver: Browse All Episodes

⏱️ Episode Time Stamps

00:00 – Alison’s background and origin story for live classes
 03:30 – The moment she knew 1:1 wasn’t sustainable
 06:45 – What “one-to-many” looks like and how they set it up
 09:00 – Tech stack: Zoom + HubSpot + Contentful
 12:15 – Self-serve signup flow and automation
 15:00 – Why one class is better than splitting audiences
 18:00 – How they measure conversions and prove ROI
 21:00 – Scaling to teammates: her exact training process
 25:00 – Why scripted sessions work (and unscripted ones don’t)
 28:00 – Tips for practicing and getting your timing right
 30:00 – Handling Q&A without derailing your session
 33:00 – How product changes impact education
 35:00 – Final advice: Just start. Don’t wait for perfect.

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 their tone guidelines
✅ The 4 key tone pillars they use to maintain consistency
✅ How they train, QA, and reinforce great communication
✅ The impact of a unified tone on trust and efficiency
✅ Steps to build your own tone document for scalable support

Links & Resources:

🔗 Listen to Priscilla Brooke on the Happy to Help podcast: https://happytohelp.buzzsprout.com/
🔗 Exclusive resources for this episode, including a worksheet and template: https://drive.google.com/drive/folders/1f3h-ZDr2Z7eSECr3Rd1h-PESsib2I1EQ?usp=sharing

Take Action:

📩 Get Weekly Tactical CX and Support Ops Tips: https://live-chat-with-jen.beehiiv.com/

🦸 Check out our sponsor: Supportman.io

Episode Time Stamps:

00:00 – Introduction to the episode & topic
 02:15 – Meet Priscilla Brooke & Buzzsprout’s Support Strategy
 05:30 – The importance of tone in written support
 10:45 – How Buzzsprout built their Tone Document
 15:20 – Training and reinforcing tone within the team
 20:40 – Measuring success & impact on customer trust
 25:55 – How you can build a Tone Document for your team
 30:15 – Final thoughts & actionable takeaways