by Lukas on 21 Oct 2026

What It Actually Takes to Win on Reddit: With Evan Hamilton (Ex HubSpot & Reddit)

It’s easy to assume that someone who has worked inside Reddit must know a secret shortcut. In our latest webinar, Evan Hamilton put that idea to rest early on: there isn’t one. Winning on Reddit comes down to hard work and listening to people.

Evan joined Rob Fawkes to share what he learned on both sides of the platform. First he worked inside Reddit, with the volunteer moderators who run its communities. Later he moved to the brand side at HubSpot, where his team set out to make Reddit work for a B2B company. Everything he shared in the session reflects his own experience and views.

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About Evan

Evan Hamilton was most recently Director of Community at HubSpot, where he built community experiences that drive customer engagement and retention. Before HubSpot, he spent five years leading community at Reddit, setting the strategy that supported tens of thousands of volunteer moderators running hundreds of thousands of communities. He’s been bringing people together professionally for over 20 years, with stints at Nextdoor, CMX, UserVoice and more. Outside work he makes music, and he co-founded International Beer Day, which grew from an idea between friends into events around the world.

A few highlights from the conversation

• Moderators hold the power: Evan joined Reddit in the aftermath of the 2015 moderator blackout, and he explained who moderators really are: unpaid volunteers who care deeply about their topic. His tip for understanding them is to think about the thing you’re obsessive about yourself.
• Go niche, not big: The biggest subreddit in your space is usually the wrong place to start. It’s the most competitive and the most defensive, and smaller, more specific communities often hold more of the audience you actually want.
• Approach moderators “hat in hand”: Learn a subreddit’s rules and unwritten norms first, then come with something genuinely valuable, like an AMA, and be ready to accept a no.
• What worked at HubSpot, and what didn’t: Evan talked through co-moderating the HubSpot subreddit, running AMAs, and why asking existing customer advocates to join Reddit had mixed results before an employee advocacy programme took off.
• Reddit and AI search: People want human perspectives, whether they’re adding “reddit” to a Google search or asking an AI tool. Evan sees Reddit as an essential part of an AI visibility strategy, but not the whole of it, and warned that shortcuts like bots and purchased accounts end in bans.

The audience Q&A covered Reddit ads, local subreddits, keeping science and health content accurate, adding value in book publishing, and what to do when a competitor spreads outdated information about your brand.

We’ll be following this up with a deeper piece on the specific tactics and takeaways from the session, so keep an eye out for that.

Catch up on the rest of the series

This was the third webinar in our Reddit series. If you missed the earlier sessions, you can catch up here:

• Keith Nieves, Sonos: What Sonos learned about winning on Reddit
• Rachel Duffy, The Times: What It Actually Takes to Win on Reddit