Leaders Fund

www.leaders.vc

VCMatch tracks Leaders Fund as an investor focused on Enterprise SaaS, Cybersecurity, and Cloud Infrastructure companies, Seed and Series A rounds, Canada, United States, and Israel markets, and $20m check sizes. Upload your deck to compare your startup against the full private matching profile.

Check Size

$20m

Stages

Seed, Series A

Focus Areas

Enterprise SaaS, Cybersecurity, Cloud Infrastructure

Geography

Canada, United States, and Israel

Investment Thesis

Leaders Fund believes in backing exceptional teams building transformative, mission-critical technology companies through a hands-on, operator-led approach. Their philosophy is rooted in deep operational experience—the team has built, backed, and exited 14 companies including multiple unicorns—and they leverage this to provide tactical, non-nonsense guidance beyond capital. They focus on compounding value over time through selective, high-conviction investments rather than chasing quick wins.

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Investment Focus

Who should take a closer look

Leaders Fund is most relevant for founders raising Seed and Series A rounds in Enterprise SaaS, Cybersecurity, Cloud Infrastructure, and AI/ML, especially across Canada, United States, and Israel, with public check-size signals around $20m.

Focus statement

Leaders Fund invests in Seed and Series A stage SaaS, cloud infrastructure, cybersecurity, and data/AI companies with $100M+ ARR potential, led by world-class founding teams building mission-critical products. They operate selectively, investing in up to three new companies per year across Canada, the US, and Israel, with check sizes up to $20M.

Value Add

Operator-first approach: All three managing partners (David Stein, Steve DeBacco, Gideon Hayden) are ex-operators who have built and exited companies themselves
Selective by design: Invest in only 3 new companies per year to ensure full attention and hands-on support
Proven track record: 9 in 10 portfolio investments raised successful follow-on rounds; 1 in 3 core investments reached $1B+ valuation; 14 exits total
True founder alignment: Help founders achieve outcomes based on their goals and definition of success, not just firm targets
Long-term, flexible capital: Focus on compounding value over time while remaining flexible on exit timing
High-velocity community: Access to network of world-class operators and advisors providing strategic guidance