Kirk Simpson
Angel Investor
Toronto, Canada
Kirk Simpson is a seed investor in Toronto focused on Software and Finance. 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.
- Total investments:
- 7
- Last investment:
- Lead investor:
- 0%
Last updated:
For AI agents: llms.txt
Industries Kirk Simpson invests in
Stages Kirk Simpson invests in
Countries Kirk Simpson invests in
Round sizes
Contacts
| Type | Contact | Validation |
|---|---|---|
| Work email | ||
| Personal email | ||
| Work phone | ||
| Personal phone | ||
| Socials |
Round size
- Seed
- $1.6M–$11M
- Series A
- $27M–$30M
Investment Focus
Industry
- Software 4 (57%)
- Finance 3 (43%)
- Sales 2 (29%)
- FinTech 2 (29%)
- Accounting 2 (29%)
Stage
- Seed 4 (57%)
- Series A 2 (29%)
- Angel 1 (14%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
| Mantle is building the next generation of tools to transform how private assets are managed. | $10.5M / Seed / Oct 12, 2023 | ||
| Ten Key Labs develops a transparent operating system with the goal of bringing programmable money to businesses. The company provides a next-generation platform for modern entrepreneurs that is powered by AI. | $7.7M / Seed / Oct 03, 2023 | ||
| Float offers a corporate card and spends management solution that allows managing corporate cards, reimbursements, approvals, and invoices. The company was founded in 2019 and is headquartered in Toronto, Ontario. | $27.1M / Series A / Nov 03, 2021 | ||
| 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. | $29.9M / Series A / Nov 03, 2021 | ||
| Uvaro's career success platform includes training, paid experience, advancement and ongoing coaching to ensure long-term career success. Our training program includes on-demand and live classes, our virtual internships let companies hire talent based on performance, our coaching and mentorship network drive ongoing career growth. Our averagestudent lands their new role in less than 17 days from graduation at more than 2x their previous income, and in their new roles achieve 50% more sales than their peers. | $1.6M / Seed / Sep 01, 2020 | ||
| Uvaro's career success platform includes training, paid experience, advancement, and ongoing coaching to ensure long-term career success. Their training program includes on-demand and live classes. Their virtual internships let companies hire talent based on performance. Their coaching and mentorship network drive ongoing career growth. | $1.6M / Seed / Sep 01, 2020 | ||
| They have built digital agencies, ecommerce businesses, and even toured in a rock band. They understand things that traditional banks don’t and that’s given us the freedom to think big. | $462K / Angel / Jun 11, 2018 |
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FAQ
What does Kirk Simpson invest in?
Kirk Simpson invests primarily in Software, Finance and Sales startups, most often at Seed and Series A stage. Most of the 7 investments tracked by Shizune back companies in Canada. The Investment Focus section breaks down every industry, stage and country in the portfolio.
What is Kirk Simpson's check size?
Kirk Simpson typically joins rounds of $1.6M–$11M at Seed and $27M–$30M at Series A. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds Kirk Simpson participates in.
How do I contact Kirk Simpson?
Public channels for Kirk Simpson include LinkedIn, X (Twitter) and the website linked on this profile. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.
When did Kirk Simpson last invest?
The most recent investment recorded for Kirk Simpson closed in Oct 2023. Shizune tracks 7 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Sep 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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