Kyle Jepson Did the Unscalable Thing First

Seven lessons from HubSpot’s first Evangelist on how years of showing up turned into 40,000 followers and a job that didn’t exist.

When I asked Kyle Jepson how he planned his path to becoming HubSpot’s first Evangelist, he said there wasn’t one. “I just turned on my webcam and started recording videos… There wasn’t a plan, there wasn’t a goal.”

There may not have been a plan, but there were seven years of showing up, testing what worked, and doing the work most people skip. Here’s what we learned:

Do the unscalable thing first

Before Kyle ever posted a video, he spent almost seven years doing something most people would call a waste of time. Every day, he searched LinkedIn for people who had posted a certificate from one of his HubSpot Academy courses. He liked the post, wrote a personal note, and sent a connect request.

Part of it was for him. “When you create an online course and you publish it, no one cheers. There’s no big splash.”

So when a friend asked LinkedIn for the most underrated HubSpot feature at the end of 2020, and Kyle answered with a 30-second video about the deduplication tool, he wasn’t starting from zero. He had 2,000 connections who were, in his words, “self-selected HubSpot nerds.” He built that audience one connection at a time.

Give people what they actually want

A few weeks into a resolution to post every day, Kyle ran out of ideas. So he posted the only update he had: HubSpot’s UI was now available in Italian. It was his first video that really took off, and nobody cared about Italian.

“They don’t need me to be like, hey, did you know this is how you create a record in HubSpot? They need to know the new stuff.”

That became the job. He’s posted product updates almost every day since, and in spring 2023, HubSpot made it official with a role that hadn’t existed before. Read the full story and ask Kyle a question on Trove.

Read your comments like research

Post every day and you start to notice who shows up. For Kyle, it was the same five or six people, and every one of them was a HubSpot admin. The company line at the time was that HubSpot was so easy it didn’t need admins.

“I was told those people don’t exist. So clearly they exist, they’re here commenting on my post.”

Stick to your guns when you have a hunch

In 2022, Kyle pitched an INBOUND talk just for admins. The organizers weren’t sure anyone would come. There were lines out the door. He started a weekly admin user group, and this year, after getting a subdomain past the security team and turning down every shortcut, he launched admins.hubspot.com.

“You did it for developers, you’re going to do it for admins.”

Read how he got it built.

Make your haters your superfans

My favorite of Kyle’s stories is the one where he leaned into his dissenters. His sales enablement course got torn apart on an industry forum by people who knew the subject better than he did. Instead of ignoring them, he apologized, read their books, interviewed them, and put them in the next version.

“Once I reached out to them and interviewed them… then they started promoting it.”

One course became three, with more than 55,000 certifications. Read the full story.

Protect the relationship as you grow

Kyle has 40,000 followers now, and people still walk up to him at events like he’s an old friend. He knows it. “People really feel like I am their friend,” he told me, and he’s not willing to trade that for scale.

“If I had to sacrifice that to reach a million people, to me, that would not be a worthwhile trade.”

Look outside marketing for your best evangelist

HubSpot recently put two more people into evangelist roles, and Kyle worries a little about them. They’re expected to replicate what he built without his seven years of groundwork. Everyone wants the playbook. His advice to leaders is simpler: find the person who already lights up talking to customers.

“I suspect most companies have a guy like me somewhere… If you can just roll film and put that on social.”

They might be on your support team or your sales team. They probably don’t have a marketing title.

Best questions from the week

Dave Burgess asked how Kyle got the security and website teams, neither of which he worked on, to say yes to admins.hubspot.com. Kyle’s answer: by the time he asked, he’d been running weekly webinars for admins for a few years, which made it “pretty easy to show that there was a real community with real interest.” It still took patience, persistence, and a manager willing to help push it through. Build the proof before you make the ask.

Danielle Messler asked how he got comfortable on video. Years of recording HubSpot training videos got him used to his own voice long before social. His advice: “jump in and give it a try! Your first attempts will feel awkward, but it gets easier the more you do it.”

Ask Kyle your question

All three of Kyle’s stories are live on Trove: how he became HubSpot’s first Evangelist, how he got admins.hubspot.com built, and how he turned his loudest critics into his biggest supporters.

If something in his story made you think of your own work, that’s your question. Go ask Kyle on Trove.