Live Chat with Jen Weaver

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

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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.

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