In this episode, Matt welcomes Willson Cross, the co-founder and CEO of Borderless AI, to discuss how AI is transforming the global HR and payroll industry. Willson shares his entrepreneurial journey, from founding and selling GoFetch to launching Borderless AI. They explore how AI-driven compliance, payroll, and onboarding are solving key challenges in hiring global teams. Willson also talks about the company’s $35M funding, its partnership with Cohere, and how they differentiate from major competitors like Deel and Rippling.

About Willson Cross:

Willson Cross is the Co-Founder and CEO of Borderless AI, a global payroll platform that uses generative AI to streamline hiring, managing, and paying international employees. Since launching in 2023, the company has raised $27 million from top investors, including Susquehanna and Bernard Arnault. Based in Toronto, Willson leads the team in building AI-powered solutions for the future of work.

Before Borderless AI, Willson co-founded GoFetch, Canada’s leading pet services marketplace. Starting from his basement in 2015, he grew the company to seven markets, raised $3.5 million, and led a team of 45 before selling the business in 2018. Earlier, he launched UBC Bitcoin Jobs, an online job board that connected university students with cryptocurrency startups, matching over 80 students to 20 companies.

Originally from Vancouver, Willson studied economics at New York University before leaving after his third year to pursue startups full-time.

⏱ Topics

* (1:26) – Willson’s background & founding GoFetch

* (2:59) – Key lessons from running a bootstrapped startup

* (4:55) – The transition to Borderless AI & identifying HR’s biggest challenges

* (6:33) – Payroll & benefits: The first major opportunities

* (6:52) – Building real-time global payroll infrastructure

* (7:50) – Meeting co-founder Sean Agarwal & forming a strong partnership

* (9:45) – AI’s role in HR compliance, payroll & automation

* (12:04) – How Cohere’s AI models enhance HRGPT

* (15:48) – Competing with Deel & Rippling as an AI-native company

* (18:19) – Pricing strategy & product differentiation

* (19:13) – How AI is transforming HR roles

* (20:47) – The shift toward larger early-stage funding rounds

* (24:30) – Target customers: Startups & large enterprises

* (27:41) – Why Borderless AI chose a full in-office model

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