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Live Chat with Jen Weaver
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.
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Live Chat with Jen Weaver
Courage to Teach: How Help Scout Turns Classes into Revenue
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.
