I joined HubSpot less than a year after the CRM launched. I was on the support team for this brand-new baby CRM. We were a team of about seven, and we were some of the only people in the company who knew how it worked and how customers used it. It was a free product, so there weren't any CSMs. When HubSpot Academy wanted training videos for the CRM, none of them had seen it, so they asked my manager if anyone could teach it. That's how I came over to the Academy.
HubSpot's marketing story at the time was that marketing and sales teams should work together, in one database. But when I spoke with customers, I found that marketing and sales teams usually didn't work together very well, even when they were both on HubSpot. They had different goals and spoke different languages.
I saw an opportunity to build a course that teaches marketing and sales teams how to work together. I pitched the idea to my boss at the time, Chris, asked, how do marketing and sales teams work together? I said, I don't know. But they should, and we're telling them they can. He said, well, Kyle, I don't want you to make anything up.
So I proposed finding companies whose marketing and sales teams worked well together and recording interviews with them, just as research. He said I could try, and if I found something, we'd build a course.
I started with a few HubSpot partners and asked, who do you think is really good at this? They then pointed me to clients. I asked the clients the same question, and they pointed me to authors of books they'd learned from. The list kept growing and I ended up interviewing about 40 people. This was before COVID and before Zoom, so a lot of these were in person, setting up cameras in people's offices.
Then I pitched something the Academy had never done. Instead of me summarizing it all, we'd make it more documentary style. I'd talk a little, then cut to Expert A and Expert B. HubSpot luckily was supportive of the format, and we called it the Sales Enablement Certification.
Initially, the series was met with enthusiastic reviews, that was until the Sales Enablement Association discovered it. I hadn’t been introduced yet and someone sent me a screenshot of the association's forum. Someone had written, "HubSpot thinks they can talk about sales enablement?" Someone else said they'd watched it and it was garbage. They were so angry. What they were really feeling was: Why weren't we involved? Who are these people?
I found my way into the forum and posted: “I'm the one who created that content. I'm really sorry. I messed up. I didn't know the Sales Enablement Association existed. It seems like you have a lot of great expertise here. Anyone who wants to be interviewed and put in the course, reach out. Let's make an update.”
One of the loudest critics said HubSpot didn't belong in this space at all. I looked him up. He'd published a book on sales enablement, so I bought it, took the time to read it, and it was really good. I told my boss these weren't internet trolls. These people knew what they were talking about. HubSpot flew me to San Francisco to sit in his office and record an interview with him and his co-author. It was a huge sign of endorsement from HubSpot on their belief in this project and in me.
After that interview, we published the second installment of the Sales Management Certification. This time we brought in the Sales Enablement Association, and they returned the favor by enthusiastically supporting us. I leaned into what author Jay Baer calls “hugging your haters”: instead of ignoring the people who were upset about the first edition, I got curious and listened. It paid off. The series got better, and we earned the stamp of approval from a wonderful group of experts.
Eventually, this became three courses: sales enablement, sales management, and revenue operations. The critics became some of the biggest advocates and started promoting the courses. I was hugging my haters, and it blossomed.
Along the way I got to interview sales and marketing leaders, operations professionals, authors, founders, consultants, and even business world great Clay Christensen. Some of the people I interviewed have since passed away, so the courses now feel like a tribute. Their words will live on.
That experience is why my love for HubSpot shows up on camera. This is a company that lets me try stuff. It let me interview Clay Christensen and flew me across the country to meet a couple of guys who wrote a book. When I get excited about an update to the index page in the CRM, that's where it comes from.
Key metrics
40+ expert interviews
HubSpot Academy's first documentary-style course format
1 course grew into 3: sales enablement, sales management, revenue operations
55k Lifetime certifications (and growing)
Sales Enablement - 21,881
Sales Management - 15,679
Revenue Operations - 18,136
Hubspot
