Leaders Fund Research
Investment Thesis
Leaders Fund is an operator-led venture firm based in Toronto, with offices in Atlanta and Tel Aviv. It backs founders building mission-critical B2B software that customers cannot run their business without, and it screens for companies with a credible path to $100M+ in ARR. The firm describes itself as a partner on the path to $100M ARR and puts its weight behind go-to-market: landing the first ten cornerstone accounts, pricing, sales motion and enterprise positioning. Its stated criteria are a world-class founding team, a mission-critical product, $100M+ ARR potential, clear positioning and strategy, fast and efficient growth, and a durable competitive advantage.
Stage Focus
Seed and Series A are the core, per the firm's Our Approach page. The portfolio shows entries as early as seed (Upwind 2022, Drata 2020, Ada 2017) and as late as Series B (360insights 2016), and the firm has followed on in later rounds of its winners, including Upwind's Series B and Series C in 2026.
Check Size
The firm states checks of up to $20M. Initial checks are likely smaller, with the upper end used for follow-ons.
Lead Tendency
The site does not say whether the firm leads. Blog posts on Oasis and Upwind show it participating alongside lead investors (Craft Ventures led Oasis Series B; Bessemer led Upwind Series C), while it backed Upwind at seed and has leaned in at each round. Marked as both, with low confidence.
Recent Activity
- October 2026: invested again in Upwind's $400M Series C at a $3.8B valuation, led by Bessemer with Leaders Fund and Canapi.
- July 2026: published its investment thesis for Tangos, autonomous AI for financial crime investigations.
- April 2026: invested in Oasis Security's $120M Series B (led by Craft Ventures). Cyera has since announced plans to acquire Oasis.
- February 2026: invested in Matia's Series A, a unified DataOps platform.
- January 2026: doubled down on Upwind at its Series B at a $1.5B valuation.
- July 2025: invested in Vellum, personal AI.
The firm is evergreen in style and says it invests in up to three new companies per year, so selectivity is high and the pace of new logos is slow.
Portfolio Highlights
The firm reports 15 exits and says one in three core investments has reached a $1B+ valuation. Highlights are Upwind (cloud security, $3.8B), Drata (compliance automation, $2B), Ada (agentic customer support, $1.2B), Snyk (developer security), OpenAI, Spot (cloud optimization, acquired by NetApp), Qwak (MLOps, acquired by JFrog), Kindred (robotics, acquired by Ocado for $262M), Flashpoint (threat intelligence, acquired by Audax), Helpful (acquired by Shopify), Zaius (acquired by Optimizely), Influitive and Peek. Active names include CallRail, 360insights, CereTax, CrowdRiff, Mantle, Matia, Seegrid, Spatial, Threekit, Toolpath and Vellum.
Team
- Gideon Hayden: Co-Founder and Managing Partner. Co-founded Tradyo (sold to Torstar), then spent years at OMERS Ventures on deals such as Shopify, Hootsuite, 360 Insights and Jobber, and was part of the founding team of OneEleven. Focus is early-stage cloud infrastructure, cybersecurity and ML/AI.
- Dave MacDonald: Venture Partner, former CEO of Softchoice, joined in 2019.
- The firm also lists a High Velocity Community of operator advisors: Galina Antova (Claroty), Spencer Pingry (Cloud Capital), Ken Allen and David Priemer (Cerebral Selling). The public team page did not render other investment team members.
Decision Process
Not publicly described. The small team and the three-new-companies-per-year cap point to a partnership decision process with high conviction on few deals.
Founder Preferences
The firm favors experienced, operator-minded teams selling to the enterprise, and emphasises true founder alignment, meaning it helps founders reach their own definition of success, including flexibility on an earlier exit. Several founders (Amiram Shachar of Spot then Upwind) have come back to it a second time.
Geographic Focus
Canada, the US and Israel. The firm also publishes research on Canadian startup attrition and advocates for Canadian founders.