The VETTDD 50 · UK startups · 2026AI and data
Matt Wilson
Co-founder and CEO, Jack & Jill · jackandjill.ai ↗
Jack & Jill puts an AI agent on each side of a hire, one for the candidate and one for the employer. In under two years its chief executive has signed up more than 5,000 hiring companies
- Series A, September 2026
- $40m
- companies hiring through Jill
- 5,000+
- candidates using Jack
- 380,000
- year Jack & Jill was founded
- 2025
Matt Wilson is co-founder and chief executive of Jack & Jill, which he founded in London in early 2025 with Saaras Mehan, its chief technology officer. Wilson previously founded Omnipresent, the employment and HR technology company, which the company says he took to a $600m (£447m) valuation in three years. Mehan founded Kular.ai, a Y Combinator-backed startup.
Two agents, one introduction
The product is two AI agents. Jack interviews job seekers in a 20-minute voice conversation, builds a profile and brings them matched roles, mock interviews and coaching. Jill works with employers to define a role and find candidates who fit it. The company earns a fee when a hire is made.
Wilson’s case is that hiring has barely changed in two decades. “There hasn’t been a major change in how people find jobs since LinkedIn and Indeed came on the scene 20 years ago,” he told TechCrunch in October 2025. Mehan put the problem this way when the Series A was announced: “Candidates struggle to be seen, while employers cannot tell who is serious.”
From seed to Series A in 11 months
Jack & Jill raised a $20m seed round led by Creandum in October 2025, when it had 12 staff and almost 50,000 candidates had spoken to Jack in London. On 15 September 2026 it announced a $40m Series A led by Air Street Capital, with Creandum and Madrona. By then, it says, more than 5,000 companies were hiring through Jill, including Ramp, Multiverse, Maze and Attio, and 380,000 candidates were using Jack across London, San Francisco and New York.
Why it matters to UK buyers
For UK employers and HR leaders, Jack & Jill is an early working example of agent-to-agent hiring, where software on each side screens and matches before a person is involved. It is aimed at the flood of applications that job boards generate, and it gives HR and compliance teams a concrete case for deciding how AI matching decisions should be explained and recorded. For recruitment firms, it is a new kind of competitor built around a commission on successful hires.
Wilson has built his second HR technology business in London and moved it from launch to a $40m Series A in well under two years. Jack & Jill is now a live UK test of whether AI agents can take on the matching work that recruiters and job boards have done for 20 years.