A Few Days in Toronto as Supademo Nears $5M ARR

Three years after starting Supademo, we were about to hit $5 million in annual recurring revenue. I headed to Toronto for three days with some of the people who helped us get there.

I had two goals for the trip: run a marketing hackathon focused on helping customers use Supademo across more of their teams, and spend time with teammates I hadn't had a chance to meet in person yet. There would also be good food, a few strategy sessions, and a run with Ryan.

Why I keep flying to Toronto

I try to get to Toronto every two to three months. Flying from New York City is a pain in the ass, but being at the same table with the team always makes it worth it.

Supademo is a remote-first company. We get to hire great people regardless of where they live. Most of our conversations, though, come with an agenda and a time limit. You jump on a call, work through something, and get back to your day.

It's funny how you can spend so much time talking to someone through a screen, then feel a little awkward when you're finally in the same room. You know how you work together. Getting to know each other outside that takes more effort.

That's why we put these meetups on the calendar every quarter. If we waited for things to slow down, we'd probably never do it. Coffee, beers, lunch, and dinner give us room for conversations we'd never make time for on a scheduled call.

Twenty video ideas, and nobody assigned to make them

Our first strategy session left us with about twenty video ideas and no plan for who was going to make them. A familiar problem.

One thread in the discussion was how differently solo users and larger teams need to learn the product. Someone creating demos on their own needs different guidance from a team with two or five people working together.

For teams, the questions get specific: how should they organize a workspace, tag demos, check quality, and manage publishing? Should one person be the final approver? We talked about making videos around those workflows, alongside AI tips and guidance for individual users.

Ten ideas for getting more of a team using Supademo

Day two started with a run with Ryan, then the hackathon. We focused on getting paying customers to use Supademo more broadly and more often across their teams and workflows.

We came up with ten ideas:

1. Email colleagues identified through enrichment who are on free plans.
2. Add one-click requests to join a team.
3. Automatically offer training when a workspace adds its third creator.
4. Let customers book a demo audit inside the app.
5. Create short tutorial videos for specific use cases.
6. Build booking flows for teams using Supademo only for customer success.
7. Help customer champions introduce Supademo to other teams in their company.
8. Pilot done-for-you demos and audits.
9. Proactively build demo agents for customers.
10. Test unlimited-seat offers triggered by customer behavior.

These were ideas to test. We ran a mini March Madness bracket to narrow the list to three experiments. By the end of our second workday, the plan was to ship the first one before the week was over.

We'd also run a broader company hackathon earlier in Toronto. I wrote about what the team built in our first hackathon recap. This time, we came in with a more focused question about helping existing customers use more of the product.

Talking through enterprise demos

Another discussion centered on selling Supademo to more enterprises. How much hands-on help would those customers need to get a demo agent working for their business?

We talked about a managed approach, including the possibility of demos as a service. The concern was that people might not know what to put into an agent or how to get started on their own. Helping them through that setup could be part of the engagement.

It was an open discussion about what to try, including how a service like that might be packaged. We were still working through the questions.

Making time for the people building this with me

By the end of the second day, we'd worked together, picked experiments, gone out for dinner, and even squeezed in a run. I'm still not sure Ryan could keep up.

After seven or eight hours of work, I was ready to call it. I get so caught up in what we need to ship and what we need to build every day that I don't stop to appreciate everything we've already pulled off together.

I'm glad we made time to be in the same room, meet the people we'd only known through a screen, and have dinner together.