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Top 20 Recruiting Angel Investors in Canada in May 2025

Last updated: May 2025 A list of 20 angel investors that invest in Recruiting startups based in Canada. We rank investors based on the number of investments they made in Recruiting companies from Canada. We update this investor list every month.

Top 20 Recruiting Angel Investors in Canada in May 2025

Investor	Recruiting Canada investments
Howard Stotland	1
Dr.Parker Vandermeer	1
Jafar Owainati	1
Jennifer Lum	1
Matthew Cowan	1
Micheal Hyatt	1
Gerry Pond	1
Mike Durland	1
Rand Lockwood	1
Mike Tilley	1
Marc Morin	1
Robert Justason	1
Jean Desgagne	1
David Henning	1
Anil Dharni	1
Kirk Simpson	1
Robert Chaplinsky	1
Richard Hyatt	1
Jim Osler	1
David Kassie	1

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Investor list

Howard Stotland - President @ Otimo Retail

Investment focus

Mobile, Recruiting, Human Resources
Seed
Canada

Portfolio highlights

Wirkn — Hyperlocal recruiting for retail, restaurants & hospitality.

Parker Vandermeer is an individual investor.

Investment focus

Medical, Recruiting, Health Care
Pre-Seed
Canada

Portfolio highlights

Cherry Health — Cherry Health is your medical network. Where healthcare connects, finds jobs and more.

Jafar Owainati is the Co-founder at Barley. He is a former Co-Founder at Loopio. Jafar Owainati attended Northwestern University - Kellogg School of Management and Queen's University.

Investment focus

Software, Employment, Recruiting
Pre-Seed
Canada

Portfolio highlights

Talin — Supercharge your recruting process with Talin's AI powered tools.

Jennifer Lum is a Co-Founder and Managing Partner at Biospring Partners, a growth equity firm that invests in Life Sciences Technology. She is an accomplished entrepreneur and investor. She has cofounded several companies and has worked with many others from formation through to M&A.Jennifer is a Venture Capital Advisor at Harvard BusinessSchool and an Advisor at MIT’s Martin Trust Center for Entrepreneurship. She is also an Advisory Board member at The Petrie-Flom Center for Health Law Policy, Biotechnology, and Bioethics at Harvard Law School.Jennifer co-founded Forge.AI (acquired by FiscalNote) and Adelphic (acquired by Time). She was an early team member at Quattro Wireless (acquired by Apple), m-Qube (acquired by VeriSign) and WebHosting.com (acquired by AT&T).She has also held various roles as a management consultant with financial services and technology companies.Twitter: @lum

Investment focus

Software, SaaS, Machine Learning
Seed, Series A, Pre-Seed
United States, Canada

Portfolio highlights

Invalidate — IPR-tested prior art search. The ultimate patent invalidation tool.
Infringements — Monitor your patents and get instant alerts on potential infringements.
Patented.ai — The most powerful AI engine for intellectual property.

Matthew Cowan is The Corporate Director At BitGo.

Investment focus

Mobile, SaaS, Enterprise Software
Seed, Series A, Series B
United States, Canada, Israel

Portfolio highlights

Uvaro — Start your career in tech! Learn from experienced instructors, practice new skills and get feedback in a supportive community. Sign up today!
Hoodline — Get breaking news from Hoodline's local reporters with stories to inform you about politics, weather, real estate, business, dining, crime, & more.
LUUM — LUUM Lash is revolutionizing the beauty industry with the world's first robotic lash extensions. The power of machine learning, AI and robotics combine to help lash artists improve efficiency, precision and overall results.

Michael Hyatt is the Executive Chairman and Co-Founder of BlueCat Networks and a recipient of the Top 40 Under 40™ Award. BlueCat is a four-time winner of “Deloitte’s Fast 50” and has received Gartner’s highest “Strong Positive” rating. Michael also co-founded Dyadem, a highly successful software company that was acquired by IHS (NYSE: IHS).Michael is a weekly business commentator on CBC Newsworld and has been featured on the cover of Canadian Business Magazine. He is also a finalist in Ernst & Young’s Entrepreneur of the Year Award and an active participant and lender for three special charities: Kiva.org, OneProsper and Future Possibilities for Kids.

Investment focus

Software, SaaS, Self-Storage
Seed, Series A, Funding Round
Canada, United States

Portfolio highlights

MinuteBox — Secure legal entity management in the cloud. Minute books, transactions, compliance, document assembly, cap tables, e-signature, automated workflows
Enso Connect — Seamless digital guest experience from booking through the entire stay and long-lasting relationships after check-out. Vacation rentals & Hotels remarketing tool.
GoBolt — Elevate your logistics game while reducing your carbon footprint with GoBolt, your trusted 3PL provider focused on sustainability.

Gerry Pond is the Co-Founder and Chairman of Mariner Innovations. He previously worked at Aliant Telecom as a President. Gerry Pond The University of New Brunswick.

Investment focus

Software, Human Resources, Enterprise Software
Seed, Funding Round, Series A
Canada, United States

Portfolio highlights

R17 — R17 (was RUMAnalytics) measures, monitors, diagnosis and optimizes websites for speed. Faster websites have higher conversion rates, lower bounce rates, higher search engine rankings, lower bandwidth costs and a better user experience on personal computers and mobile devices.They created R17 to make the internet faster. R17 combines theworld's foremost experts on performance optimization with easy-to-understand analytics, actionable recommendations and mind-blowing CDN technology.
Alongside — The perfect hire is closer than you think. Source better candidates, provide great candidate experiences & give yourself the freedom to find the perfect fit.
Porpoise — Porpoise is an employee engagement platform for companies that have corporate responsibility initiatives and are looking to automate involvement, measurement and reporting. Porpoise makes it simple to recognize, capture, and amplify the social impact that employees are making on behalf of your company, finally giving your marketing departments thecontent they need to deliver great campaigns, and HR managers the data to track and manage employees engagement programs and targeted initiatives.Spend less time managing your impact and giving programs, and more time accelerating the impact!

Mike Durland is the former Group Head and CEO, Global Banking and Markets, for Scotiabank. He retired from Scotiabank in 2016 to pursue a variety of business, philanthropic, and academic interests. Today, he is the CEO of Melancthon Capital, a member of the Business Strategy Committee for the Global Risk Institute, the Chair of the Board ofDirectors of DeepLearning, a founding principal in Cabot Links, a member of the Board of Directors of TruLeaf Sustainable Agriculture, a member of the advisory board of Riipen Networks Inc., a member of the Board of Directors of the Dalhousie Medical Research Foundation, a member of the Advisory Board of the Smith School of Business at Queen’s University, and a member of the Advisory Boards of the Center for Social Impact and the Master of Management Analytics Program, both at Queen’s University. He holds a B.Comm degree from St. Mary’s University, a PhD in Finance and Operations Research from Queen’s University, and an honorary doctorate from St. Mary’s University.

Investment focus

SaaS, Software, Recruiting
Funding Round
Canada

Portfolio highlights

TruLeaf —
Ideal — Ideal is a talent intelligence system that helps enterprise teams make more accurate, efficient, and fair decisions. Discover our product!

Rand Lockwood joined Recruit N Refer as Co-Founder.

Investment focus

SaaS, Accounting, Recruiting
Pre-Seed
Canada

Portfolio highlights

Recruit N Refer — We bridge the gap between top-tier candidates and accounting firms

Mike Tilley

Investment focus

SaaS, Software, Recruiting
Funding Round
Canada

Portfolio highlights

Alongside — The perfect hire is closer than you think. Source better candidates, provide great candidate experiences & give yourself the freedom to find the perfect fit.

Marc, our Chief Executive Officer, co-founded Sandvine (TSX:SVC) and served as its Chief Technology Officer, developing the company's vision and technology strategy. Prior to Sandvine, he was co-founder at PixStream which was acquired by Cisco Systems.

Investment focus

Software, Internet, Machine Learning
Seed, Series A
Canada

Portfolio highlights

Uvaro — Start your career in tech! Learn from experienced instructors, practice new skills and get feedback in a supportive community. Sign up today!
Dejero — Dejero delivers resilient, uninterrupted internet connectivity for data-intensive applications by intelligently combining multiple networks into a single managed service.
Sortable — Sortable is an agnostic, low-cost, broad spectrum platform that helps publishers unify demand partners, data, and tools. We’ve developed a best-in-class UI that contextualizes this data, allowing publishers to more deeply understand the correlation between content, marketing, and monetization.Their ultimate goal is to simplify the complexities ofpublishing operations while generating more revenue for their publisher partners.Sortable began as an online publisher, building 20 websites and apps to help consumers compare competing products in a number of categories, generating over 500 million product comparisons since their creation. In 2014, after realizing that the experience gained from building websites was better used to help fellow publishers, Sortable launched the machine learning ad optimization focused technology company that you see today.

Bob is chief operating officer and co-founder of Mariner. Prior to joining the Mariner team, Bob held a variety of senior positions with NBTel and Aliant Telecom, including VP, Broadband Engineering, VP, Engineering and VP, Technical Solutions and Support.Bob’s expertise spans the full range of IP and broadband networking applications andtechnologies. In addition to leading Aliant Telecom’s Broadband infrastructure deployment, Bob directed the development of industry-first IP applications, including IP Centrex, TV on the PC and the world’s first IP TV service to deliver multiple MPEG TV streams on DSL technology. Bob has also led the technology development and implementation of self service and service improvement software and tools for both HSI and IP TV. Bob was instrumental in establishing NBTel as the first Canadian telephone company to provide internet service, and he led the technology strategy to deliver a widely respected contact center program which delivered over 10,000 seats of agent technology to world-leading contact center operators, including Fortune 500 clients.

Investment focus

Enterprise Software, Software, SaaS
Seed, Funding Round, Convertible Note
Canada

Portfolio highlights

R17 — R17 (was RUMAnalytics) measures, monitors, diagnosis and optimizes websites for speed. Faster websites have higher conversion rates, lower bounce rates, higher search engine rankings, lower bandwidth costs and a better user experience on personal computers and mobile devices.They created R17 to make the internet faster. R17 combines theworld's foremost experts on performance optimization with easy-to-understand analytics, actionable recommendations and mind-blowing CDN technology.
Alongside — The perfect hire is closer than you think. Source better candidates, provide great candidate experiences & give yourself the freedom to find the perfect fit.
LeadSift — We comb through the public web to deliver only qualified leads interacting with your competitors and with demonstrated buying intent.

Jean Desgagné is President and CEO, Global Enterprise Services, TMX Group, a member of TMX Group's executive management committee and is an Officer of the Corporation.Global Enterprise Services is accountable for the delivery of Technology, Operations, Transaction and Procurement Services for all of TMX.Desgagné joined The CanadianDepository for Securities Limited (CDS), a wholly-owned subsidiary of TMX Group, in 2013 from TD Bank Group where he was Senior Vice President, Trading Risk Services, holding responsibility for the independent oversight of valuation, market risk, liquidity and collateral for TD's global trading business. Prior to TD Bank, he held increasingly senior positions at some of Canada's leading financial institutions including Bank of Montreal and Union Bank of Switzerland (Canada) in areas such as treasury operations, technology, trading support and risk management.Desgagné is a Chartered Accountant and a graduate of the University of Ottawa. He currently serves on the Board of the Jean Tweed Centre, the Board of Governors of Junior Achievement of Central Ontario, and has been active in a number of other community organizations. He is a member of the President's Advisory Council for the University of Ottawa and was awarded the Trudeau Medal by the Telfer School of Management and the Queen's Jubilee Medal in 2002 in recognition of his community service.

Investment focus

Podcast, E-Learning, Employment
Seed
Canada

Portfolio highlights

Luminari — Canada's largest professional community of CPAs
LumiQ — LumiQ makes earning CPD hours fun and accessible for individual accounting professionals and teams on-the-go. Get started now!

David Henning - Partner @ Otimo Retail

Investment focus

Mobile, Software, Commercial
Seed, Funding Round
Canada, United States

Portfolio highlights

Wirkn — Hyperlocal recruiting for retail, restaurants & hospitality.
Logiwa — Logiwa is the leading cloud fulfillment software for high-volume direct-to-consumer brands, wholesalers, and 3PLs. The Logiwa Cloud Fulfillment Platform is an integrated WMS and order fulfillment system that makes it easy to run a digital warehouse and scale your high-volume DTC fulfillment operations. Logiwa’s solution works where traditional WMSsystems fail: it connects quickly with new online stores and marketplaces, makes it easy to run a digital warehouse, and is easily updated to support dynamic warehouse environments.

Anil Dharni is the Co-Founder and CEO of Sense. Attended at MIT Sloan School of Management.

Investment focus

Mobile, Apps, iOS
Seed, Series A
United States, India, Canada

Portfolio highlights

Uvaro — Start your career in tech! Learn from experienced instructors, practice new skills and get feedback in a supportive community. Sign up today!
Nuzzel — Nuzzel is a professional news discovery service used by many of the top influencers in media, technology, and finance.Nuzzel was named one of the best apps of the year by Google Play, the New York Times, Fast Company, and Time Magazine.Nuzzel is backed by top Silicon Valley investors including Andreessen Horowitz, CRV, Homebrew, LowercaseCapital, Uncork Capital, Marc Benniof, and Max Levchin.
Rover — Rover Rover is an advanced personalization and recommendation technology app. Its Recommendation Engine is also used to power discovery on numerous third party news and media sites. Rover helps people discover content they love, that they never knew existed from a wide variety of over 15,000 topics. The recommendation engine uses machine learningto learn a user's fine-grained interests through content a user engages with while being respectful of a user's need for privacy. Rover also connects to other people who are influential in topics that care about and help discover other people with similar interests. Rover uses Machine Learning to help people discover content they love that they never knew existed.It was founded in 2007 and is headquartered in Sunnyvale, California.

Kirk Simpson is the CEO of Confirm. He is a passionate team builder, innovator, and entrepreneur with more than two decades of experience leading disruptive technology ventures.Before his current role at Confirm, Kirk co-founded Wave Financial Inc., a company dedicated to providing financial services and software solutions to small businesses.Under his leadership as CEO, Wave expanded significantly, achieving $100M in annual revenue and growing its team to 370 employees. This growth culminated in Wave’s acquisition by H&R Block for $537M in June 2019.In the same year, Kirk’s exceptional leadership was recognized when he was named Canada’s Most Admired CEO in the growth category by Waterstone Human Capital.Beyond his role at Confirm, Kirk actively contributes to the North American startup ecosystem as an angel investor and advisor.

Investment focus

Finance, Software, Credit Cards
Seed, Series A, Angel
Canada

Portfolio highlights

Ten Key Labs — Mantle is a next generation ownership and equity management platform for modern founders, powered by AI.
Float Financial — Float offers modern financial services, powerful software and industry-leading support designed for every company and stage of growth. Our product suite includes corporate cards, bill pay, expense management and high-yield accounts, giving finance teams everything they need to manage spending and cash flow efficiently.
Float Financial — All-in-one corporate cards, fast bill payments, reimbursements, and expense management software. Get started today for free.

Rob Chaplinsky is the Co-Founder and Managing Director Link Ventures. Rob previously worked at Bridgescale Partners as the Managing Director. He Harvard Business School and the University of Waterloo.

Investment focus

Software, SaaS, Sales
Series A, Seed, Series B
United States, Canada

Portfolio highlights

Uvaro — Remix your favorite resources and hacks with your best company content in a personalized hub that moves as fast as your team does
Uvaro — Start your career in tech! Learn from experienced instructors, practice new skills and get feedback in a supportive community. Sign up today!
Caribou — Our customers save an average of $130/month on their car payments.

Richard Hyatt co-founded BlueCat Networks, Inc. in 2000 and has been its Chief Scientist since January 2014. Mr. Hyatt served as Chief Technology Officer and as Vice President of Engineering at BlueCat Networks, Inc and serves as its Director.

Investment focus

SaaS, Software, Commercial
Seed, Funding Round
Canada

Portfolio highlights

MinuteBox — Secure legal entity management in the cloud. Minute books, transactions, compliance, document assembly, cap tables, e-signature, automated workflows
Ideal — Ideal is a talent intelligence system that helps enterprise teams make more accurate, efficient, and fair decisions. Discover our product!
GoBolt — Elevate your logistics game while reducing your carbon footprint with GoBolt, your trusted 3PL provider focused on sustainability.

Jim Osler - Principal @ Origin Merchant Partners

Investment focus

Recruiting, Predictive Analytics
Angel
Canada

Portfolio highlights

ClearFit — Situs toto togel158 ialah toto togel online no 1 di Indonesia pada saat ini. Daftar dunia togel dan gabung bersama situs togel 158 resmi dengan harga yang lebih memuaskan togel lovers.

David Kassie - Chairman of the Board @ Clearfit Analytics

Investment focus

Recruiting, Predictive Analytics
Angel
Canada

Portfolio highlights

ClearFit — Situs toto togel158 ialah toto togel online no 1 di Indonesia pada saat ini. Daftar dunia togel dan gabung bersama situs togel 158 resmi dengan harga yang lebih memuaskan togel lovers.

Investors by industry

Artificial intelligence