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Upteaming

Upteaming runs private peer groups for founders and senior operators at venture-backed companies. Each month it matches leaders into confidential groups of three to six around the single challenge each is facing, and says it has grown from six companies to more than a thousand.

CommunityTorontoupteaming.com
1,000+venture-backed companies, up from six in a few years, on the company's own countUpteaming
3-6peers per confidential breakout group, matched monthly from forums of 25-50 leadersUpteaming
79%average progress members report on their top challenge, on the company's own reportingUpteaming

The people

Gabe DunlopChief Operating Officer · 1 TechTO talk
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Ben BaldwinFounderprofile coming

What they build

Peer ForumsMonthly facilitated 90-minute sessions matching senior leaders into confidential groups of three to six on the challenge each is facingProduct page ↗
The Founder City ProjectThe company's wider founder-community programme, run under its legal name Founder City, Inc.Product page ↗

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Working at Upteaming

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Open roles on the TechTO Job Board ↗Or their own careers page: upteaming.com/careers ↗

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About

Upteaming — legally Founder City, Inc., based on Richmond Street East in Toronto — is built on a narrow claim about how founders actually learn: not from playbooks, and not from advice, but from three or four people who have just been through the same thing. Its monthly peer forums gather 25 to 50 leaders from different companies and break them into small confidential groups matched on each person's top current challenge, rather than on industry or stage; sessions run 90 minutes and are facilitated, so a member joins when they need to rather than holding a standing slot. It insists on seniority in the match — the point is a peer who has run the problem, not a junior. The company says it has grown from six to more than a thousand venture-backed companies in a few years, and publishes its own member-reported figures: 62 per cent better at avoiding others' mistakes, 79 per cent average progress on a top challenge. Ben Baldwin founded it; Gabe Dunlop, who presented at TechTO's MarketingTO in 2019 while at Diply, is chief operating officer and co-facilitates the groups.

Backers

No funding round appears on the company's own site or in any source read for this page.

Some figures are founder-stated, not independently confirmed

Quick answers

What is Upteaming?

A private peer-network service for founders and senior leaders at venture-backed companies. Each month it matches people into small confidential groups built around the specific challenge each of them is currently facing.

How is it different from a mastermind or a founder community?

Two things it is explicit about: the match is on your current problem rather than your industry or stage, and the people in the room are senior enough to have run that problem themselves. Groups are re-matched monthly, so there is no standing calendar commitment.

How big is it?

The company says it has gone from six companies to more than a thousand in a few years, and publishes member-reported results — 79 per cent average progress on a top challenge, 62 per cent better at avoiding others' mistakes.

Who from Upteaming is in this directory?

Gabe Dunlop, its chief operating officer, who co-organises and facilitates the groups. He presented at TechTO's MarketingTO in February 2019 on ideas and creativity, at that point at Diply.

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Maintained by TechTO · facts sourced and dated · last reviewed Aug 29, 2026