Chris LoDolce on Transforming Customer Education and HubSpot's Success
Ramli John: I'm a big fan of HubSpot. They're a B2B company that pioneered offering free certification courses. One of the people behind HubSpot Academy's early success is Chris LoDolce. He's the former Director of HubSpot Academy and now the founder of SaaS Academy Advisors, where he helps SaaS companies build their own academies.
In this episode of Marketing Powerups, you'll learn:
Before we get started, I've created a free power-up spreadsheet that you can download to apply Chris's transformative customer education strategy to your business right away. You can get it now at marketingpowerups.com or find the link in the show notes and description.
Ramli John: Are you ready?
Chris LoDolce: Let's go!
Ramli John: Chris, thank you for joining. I'm super excited to talk about HubSpot Academy, SaaS Academy Advisors, and your work in helping companies build academies. I know you were one of the earliest professors at HubSpot Academy. What was that experience like? Was it a moment of excitement, or was it more of an adventure, trying to figure out how to make the academy work at HubSpot?
Chris LoDolce: Happy to give some background there. It's a really interesting story. When I joined HubSpot in 2011, there was a team of three people - Lucy Orluck, Brian Logan Reed, and Mike Ewing. They were working on what they called "one-to-many" training. Our customer base back then was mostly small businesses, with some medium and large ones. The smallest customers were paying just $50 per month.
Back then, we were onboarding customers individually for six to eight hours, which meant a long payback period. The team experimented with a series of webinars to scale customer education, but adoption was a challenge. Many of these small businesses were just getting online for the first time, and they had very basic websites - often just a single page or an uploaded image of their mailer.
For our mid-market customers, we had one-on-one consultants, which made financial sense because they were paying more. But for smaller businesses, we needed a new strategy. That led to the first iteration of "Academy," which focused on onboarding through group training rather than one-on-one sessions. While it moved the needle a bit, it wasn’t enough to be the right long-term strategy.
By 2012, we realized we were having the same conversations repeatedly in customer onboarding. Mark Killins, Julie Hogan, and a few others started "Content Camp," which introduced webinars for customers. This was novel at the time - webinars were usually lead generation tools, but we used them for education.
That led to the second iteration of HubSpot Academy, where we connected education more closely to product adoption. Our goal was simple: Get customers to use three core tools - blogging, landing pages, and email - because data showed that customers using these tools had the highest retention rates.
By 2012, we were refining our approach. We started developing one-hour training sessions focusing on inbound marketing methodology. The classes emphasized not just how to use the product but why it mattered. Our goal was to help customers understand the bigger picture - how these tools fit into their overall marketing strategy.
We also added interactive elements like real-time landing page creation and feedback sessions, which were groundbreaking at the time. These early iterations helped us refine our methodology and understand what worked.
Later, HubSpot's inbound marketing methodology evolved. Initially, it was Get Found, Convert, Analyze. Then it became Attract, Convert, Close, Delight to align better with the full customer journey. Eventually, it shifted to the Flywheel model, emphasizing force and friction in customer experience. HubSpot Academy played a critical role in educating the market during these transitions.
Without HubSpot Academy, updating our methodology and educating the market at scale would have been extremely difficult. The academy allowed us to re-educate thousands of customers, partners, and industry professionals whenever we made strategic shifts.
For example, when we moved from a linear funnel model to the Flywheel, it still took two years to fully transition. But because we had the academy, we could update certifications, create new learning materials, and guide customers through the change. This was a major advantage for HubSpot as a company.
At HubSpot, we tracked:
A great educational program isn't just about teaching features - it’s about creating transformative experiences. When customers feel like their careers or businesses have improved because of your education, they become lifelong advocates.
This approach led to a "boomerang effect" for HubSpot - customers who left often brought HubSpot into their next company because they valued the ecosystem and learning experience.
Education also plays a massive role in community building. HubSpot invested heavily in HubSpot User Groups (HUGs) and in-person events. These created deep customer relationships and a strong sense of belonging. Today, many companies are leveraging cohort-based courses and community engagement to enhance their education programs.
If I had to pick one career power-up, it’s this: Create 100 transformative educational experiences.
If you help 100 people achieve real, measurable success, you’ll have 100 advocates who can vouch for you. This principle applies whether you’re building a customer academy, launching a startup, or growing a personal brand.
I hope this conversation has been valuable. If you’re building a SaaS academy, focus on impact first, not just completion rates, but real behavior change and business outcomes.
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Thanks for listening, and see you next time!