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.