LeafLink
LeafLink operates a B2B wholesale and fintech platform for the cannabis industry, processing $5B in annual order volume. It facilitates roughly half of all regulated wholesale cannabis transactions in the US, serving thousands of licensed operators across 37 markets.
The growth story
LeafLink grew from 203 to 116 employees between 2021 and 2026, raising $479M along the way, most recently a Series D in February 2023.
About
LeafLink provides software for wholesale transactions and financial services in the cannabis sector, avoiding direct plant handling due to regulatory constraints. Its platform connects licensed growers, distributors, and retailers for compliant trade.
The company reached Series D funding in 2023 with $479M raised, though current headcount (116) suggests capital efficiency. It dominates wholesale transaction volume despite operating in a fragmented regulatory environment.
Founders and leadership
Engineering is the largest department with 22 staff. Leadership appears decentralized given the median tenure of 2 years and multiple acquired brands (Leaf Trade, Dama Financial) operating under the LeafLink umbrella.
The LeafLink org chart
Ashwin Raj (Chief Executive Officer) leads 43 mapped leaders with 3 direct reports. Click +N to expand a team; names link to the person’s public profile.
Departments, and which ones grew
Headcount by function: Engineering 24 (-50% YoY), Sales 19 (-27% YoY), Operations 11 (-8% YoY), Information Technology 11 (-35% YoY), Business Development 11 (-21% YoY), Finance 7 (-42% YoY).
Talent flow
LeafLink draws heavily from cannabis-adjacent fintech (Dama Financial, Weedmaps) and e-commerce (Amazon, ezCater). Alumni frequently move to financial services (BasePoint Group, Apollo) and vertical SaaS companies like monday.com.
Most common previous employers of LeafLink staff: Dama Financial by LeafLink® (10), Amazon (6), U.S. Bank (4), Weedmaps (3), Leaf Trade by LeafLink (3), ezCater (2). Former LeafLink employees most often moved to BasePoint Group (8), Justworks (3), Scribd (2), monday.com (2), Apollo Global Management (2), ServiceTrade (2).
Alumni worth knowing
The LeafLink mafia
19 alumni-founded companies include Trullion (119 staff) and Scale Army (76 staff), showing entrepreneurial spillover from LeafLink's early position in cannabis fintech.
19Artie Minson, was President and CEO and Board Member until 2025Alex Kruger, was Investor until 2018Kenny Gary, was Director of Business Development, Strategic Accounts until 2022Gabby Choi, was Senior Director, West Coast Region (Regional GM) until 2022Zachary Silverman, was Co-Founder & CTO until 2023Erik Dawson, was Sr Director, Product Management until 2023
Karan M Gupta, was Chief Technology Officer until 2023
Gabrielle (Moretto) Hunter, was Strategic Partnerships Manager until 2023
Thomas Wilson, was Senior Backend Engineer until 2020
Cosimo Leone, was Software Engineer until 2019
Sam Lee, was Chief Revenue Officer (CRO) until 2025
Luca Alessandrini, was Senior Account Manager - LeafLink Payments until 2023
Andrew Plonsker, was Head of Brand & Retail Sales until 2025
Rebecca Campbell, was Director of Client Experience and Support until 2023
Christine Harrell, MBA, CCCP, was Manager, Account Management, Payments until 2023
Carrissa Menendez, was SVP, Head of People until 2022
Kailyn White, was Advisor, GTM Strategy & Operations until 2022
Joel Wisdo, was Director of Operations and Expansion until 2017Hiring now
Web traffic
Traffic mix: 80% direct, 9% search, 2% social, 1% paid.
What this company is made of
Most common skills at LeafLink: Leadership (44), Customer Service (43), Data Analysis (42), Microsoft Excel (41), Microsoft Office (41), Management (40), Python (Programming Language) (40), Marketing (37).
Where the team actually sits
LeafLink people are concentrated in New York, United States (11), California, United States (10), New York City Metropolitan Area (8), San Francisco Bay Area (5).
Search footprint
LeafLink attracts about 3,850 organic search visits a month, traffic worth roughly $3K a month if bought through ads. It gained 240 ranking keywords and lost 180 in the last period.
What employees say
- Compensation
- 3.40 / 5
- Career opportunities
- 2.80 / 5
- Senior management
- 2.10 / 5
- Work-life balance
- 3.50 / 5
Frequently asked
LeafLink has 116 employees as of September 2026.
LeafLink has raised $479M in total, most recently a Series D round in February 2023.
Ashwin Raj (Chief Executive Officer) sits at the top of LeafLink's reporting structure, with 3 direct reports.
The most common previous employers of current LeafLink staff are Dama Financial by LeafLink® (10 people), Amazon (6 people), U.S. Bank (4 people).
Former LeafLink employees most often move to BasePoint Group (8), Justworks (3), Scribd (2).
At least 19 companies have a founder who previously worked at LeafLink, including Trullion, Scale Army, LIMELIGHT.
LeafLink attracts about 3,850 organic search visits a month, worth roughly $3K a month in equivalent ad spend.
The most common skills among LeafLink staff are Leadership, Customer Service, Data Analysis, Microsoft Excel, Microsoft Office.
LeafLink staff are concentrated in New York, United States (11), California, United States (10), New York City Metropolitan Area (8).
LeafLink has about 24 people in Engineering, down 50% over the past year, as of September 2026.
LeafLink has about 19 people in Sales, down 27% over the past year, as of September 2026.
Computed from 87 current and 283 former LeafLink profiles, as of September 2026. Source: Crustdata.
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