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The Venture Codex

Leaders Fund

20 Eglinton Ave W, Toronto, Ontario, M4R 1K8, Canada

Overview

Venture capital firm investing in early-stage enterprise software companies

Founded

2016

Deals ยท 12mo

4

Links

WebsiteLinkedInX (Twitter)

Stage focus

Seed
Series A
Series B

Geographic focus

Canada
Israel
Poland
United States

Sector focus

Finance
Financial Services
Venture Capital

Investment portfolio

36rounds
NAMEDATESIZE
Upwind Security
Sep 2026Participated
$300 MOther Equity
Tangos
Jul 2026Participated
$20 MSeed
Matia
Feb 2026Participated
$21 MSeries A
Upwind Security
Jan 2026Participated
$250 MSeries B
Vellum
Jul 2025Led
$20 MSeries A
Upwind Security
Dec 2024Participated
$100 MSeries A
Matia
Oct 2024Led
$11 MSeed
CereTax
Jun 2024Participated
$9 MOther Equity
Ask-AI
Jan 2024Led
$11 MSeries A
Upwind Security
Sep 2023Led
$50 MOther Equity
Qwak
Mar 2023Participated
$12 MSeries A
Upwind Security
Sep 2022Led
$30 MSeed
Upwind Security
Sep 2026Participated
$300 MOther Equity
Tangos
Jul 2026Participated
$20 MSeed
Matia
Feb 2026Participated
$21 MSeries A
Upwind Security
Jan 2026Participated
$250 MSeries B
Vellum
Jul 2025Led
$20 MSeries A
Upwind Security
Dec 2024Participated
$100 MSeries A
Matia
Oct 2024Led
$11 MSeed
CereTax
Jun 2024Participated
$9 MOther Equity
Ask-AI
Jan 2024Led
$11 MSeries A
Upwind Security
Sep 2023Led
$50 MOther Equity
Qwak
Mar 2023Participated
$12 MSeries A
Upwind Security
Sep 2022Led
$30 MSeed
36
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Insights

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Deal Distribution

Leaders Fund: 36 funding rounds are recorded in the selected participation categories.All available history.
Leaders Fund: 36 funding rounds are recorded in the selected participation categories. All available history
Round typeLed dealsParticipated deals
Seed33
Series A38
Series B18
Series C+02
Other Equity35

Monthly Deal Activity

Leaders Fund: 36 deals are recorded across 128 months.All available history.
Leaders Fund: 36 deals are recorded across 128 months. All available history
MonthDeals
Mar '161
Apr '160
May '160
Jun '161
Jul '161
Aug '160
Sep '160
Oct '160
Nov '160
Dec '160
Jan '170
Feb '170
Mar '170
Apr '170
May '170
Jun '170
Jul '171
Aug '170
Sep '172
Oct '170
Nov '170
Dec '170
Jan '180
Feb '180
Mar '180
Apr '181
May '180
Jun '180
Jul '180
Aug '181
Sep '180
Oct '181
Nov '180
Dec '182
Jan '190
Feb '190
Mar '190
Apr '190
May '190
Jun '190
Jul '190
Aug '190
Sep '190
Oct '190
Nov '190
Dec '190
Jan '201
Feb '202
Mar '202
Apr '200
May '200
Jun '200
Jul '200
Aug '200
Sep '200
Oct '200
Nov '200
Dec '201
Jan '211
Feb '210
Mar '210
Apr '210
May '210
Jun '211
Jul '210
Aug '211
Sep '210
Oct '210
Nov '212
Dec '210
Jan '220
Feb '221
Mar '220
Apr '220
May '220
Jun '220
Jul '220
Aug '221
Sep '221
Oct '220
Nov '220
Dec '220
Jan '230
Feb '230
Mar '231
Apr '230
May '230
Jun '230
Jul '230
Aug '230
Sep '231
Oct '230
Nov '230
Dec '230
Jan '241
Feb '240
Mar '240
Apr '240
May '240
Jun '241
Jul '240
Aug '240
Sep '240
Oct '241
Nov '240
Dec '241
Jan '250
Feb '250
Mar '250
Apr '250
May '250
Jun '250
Jul '251
Aug '250
Sep '250
Oct '250
Nov '250
Dec '250
Jan '261
Feb '261
Mar '260
Apr '260
May '260
Jun '260
Jul '261
Aug '260
Sep '261
Oct '260

Sector Breakdown

Leaders Fund: Enterprise Software is the largest displayed sector by deal count (23 deals).All available history.

A deal can appear in multiple sectors, so sector totals may overlap. Capital represents disclosed total round sizes, not fund cheque sizes.

Leaders Fund: Enterprise Software is the largest displayed sector by deal count (23 deals). All available history
SectorDeals
Enterprise Software23
AI & Machine Learning14
Networks, Cloud & Communication13
Cybersecurity & Privacy11
Professional Services10
Data, Analytics & IT9
Marketing & Advertising5
Developer Tools5
Fintech4
E-Commerce & Retail3
Hardware & Robotics3
Education & Workforce2
Space & Frontier Tech2
Media & Entertainment2
AR/VR1
Consumer & Lifestyle1
Crypto & Blockchain1
Manufacturing1

Deal Size Distribution

Leaders Fund: 36 rounds have a disclosed size in the displayed size bands.All available history.

Undisclosed round sizes are excluded. Capital represents total round sizes, not fund cheque sizes.

Leaders Fund: 36 rounds have a disclosed size in the displayed size bands. All available history
Round size band (USD)Deals
<$5M3
$5M-$10M4
$10M-$25M13
$25M-$50M8
$50M-$100M4
$100M-$250M2
$250M-$500M2
$500M-$1B0
$1B+0

Deals By Geography

Leaders Fund: United States has the largest recorded deal count among the displayed regions (23 deals).All available history.

Top 4 of 4 regions; European countries are grouped as Europe.

Leaders Fund: United States has the largest recorded deal count among the displayed regions (23 deals). All available history
RegionDeals
United States23
Canada7
Israel4
Europe2
Leaders Fund: 20 co-investors are shown, with Bessemer Venture Partners sharing 7 recorded deals.All available history.

Co-Investors

Bubble size = shared deals

Click a bubble to open that fund in a new tab.

Shows up to 20 co-investors ranked by shared deals. Deals may be shared with multiple funds, so rows overlap. Capital is total round size, not fund cheque size.

Leaders Fund: 20 co-investors are shown, with Bessemer Venture Partners sharing 7 recorded deals. All available history
Co-investorShared deals
Bessemer Venture Partners7
Cerca Partners6
Cyberstarts5
Greylock Partners5
Version One Ventures5
Craft Ventures4
FirstMark Capital4
Penny Jar Capital4
Alta Park Capital3
Burst Capital3
Cowboy Ventures3
Georgian Partners3
Salesforce Ventures3
Sheva3
TCV3
Accel2
Amiti Ventures2
BDC Capital2
Bloomberg Beta2
Caffeinated Capital2

Investment Strategy

Leaders Fund: Led accounts for 28% and participating for 72% of round participation.All available history.
Leaders Fund: Led accounts for 28% and participating for 72% of round participation. All available history
CategoryDeals (count)Share (%)
Led1028%
Participating2672%
Leaders Fund: Single-lead accounts for 50% and co-led for 50% of lead dynamics.All available history.
Leaders Fund: Single-lead accounts for 50% and co-led for 50% of lead dynamics. All available history
CategoryDeals (count)Share (%)
Single-lead550%
Co-led550%

Team

Bryan W. Kerdman

Venture Partner

David MacDonald

Venture Partner

David Stein

Founder & Managing Partner

Gideon Hayden

Co-Founder & Partner

Stephen DeBacco

Co-Founder & Managing Partner