
In this episode, we'll dive into the evolution of HubSpot Academy and learn how it went from a one-person webinar to a global team of 65.
Meet our Guest
Courtney is the Senior Director of HubSpot Academy, where she combines her passion for education and inbound marketing to shape the customer education landscape. She excels at stakeholder collaboration, adapting to evolving global markets, and developing top-tier talent.
With deep expertise in inbound marketing and scaling educational programs, Courtney is a visionary educator who champions the transformative power of inbound marketing. Through her leadership, she leverages educational content and achievements to drive both individual and organizational growth.
From non-profit to public SaaS powerhouse
Background context: Ten years ago, Courtney Sembler left the nonprofit world, packed up her life on the West Coast, and joined HubSpot as a support engineer — despite failing math in school and her parents worrying she wasn’t “really” an engineer.
That leap started a decade-long climb through HubSpot’s education team, where she helped evolve HubSpot Academy from a small team running live webinars into a global program now responsible for over **700,000 leads annually** and a **13% increase in customer retention**.
🎤 “I started teaching email marketing. Now our team supports six languages, drives real business metrics, and influences onboarding, activation, and retention at scale.” — Courtney Sembler
Key Insight #1: Start Small
Courtney’s team didn’t try to do everything from the start. They focused on one executive pain point—retention, and proved value through targeted webinars.
That initial win helped earn buy-in and resources to expand.
🎤 “Find the virtual whiteboard. It’s usually retention, acquisition, or activation. Solve one first. We started with retention — and we stuck to live content.” — Courtney Sembler

Key Insight #2: Global Content Requires Local Context
HubSpot Academy now spans 65 team members across various regions, creating content in six languages. But Courtney cautions: translation isn’t enough.
Her team’s structure includes education, operations, program management, and enablement. Each mapped to a core business metric.
🎤 “You can’t just localize. You need regional context. We have people on the ground to make it relevant.”— Courtney Sembler

Key Insight #3: Education Thrives on Relationships
Courtney emphasizes that customer education must not live in a silo. Her team “packed light and traveled well,” moving between CS, marketing, and brand functions to build trust.
That strategy enabled them to co-launch HubSpot’s ChatGPT integration with full enablement content — on Day 1
🎤 “We can’t be the team in the corner. You have to walk 85% of the way. Build relationships before you need them.” — Courtney Sembler

Free Adoption Template: Customer Education Activation Playbook
The Problem: Getting early leadership buy-in for customer education.
The Solution: Use this 5-step worksheet.
- Identify your org's most urgent metric: retention, acquisition, or activation.
- Design one educational initiative to directly impact that metric.
- Start with live content or webinars (quickest to ship).
- Measure outcomes—not just attendance, but impact.
- Use the win to expand: certifications, async, automation.
Why this Works: Focus on the problem your execs are already white boarding. That's how you get in the room and stay there.
Customer Education Activation Playbook
Learn how to structure your education efforts around three key business outcomes: Acquisitions, Activation, and Retention.
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