Jack and Jill raises a $40m Series A led by Air Street Capital, with Creandum and Madrona participating, after growing revenue about 40 times since its $20m seed round.
Matt Wilson says Jack and Jill raised its minimum engineer pay to £360,000 from £240,000 nine months earlier, because AI agents let one product engineer do work that once needed a full team.
Wilson says the company lets employees choose their own cash-to-equity mix, since two thirds of its team are former founders and staff have many options, including moving to San Francisco.
AI hiring startup Jack and Jill raises $40m to expand in the US
Jack and Jill is building a two-sided hiring marketplace run by AI agents, one for candidates and one for employers, and has raised $40m to push it across Europe and the US. Wilson argues that agents let a small team of top product engineers do the work of many, which justifies very high pay and constant rebuilding of the product.
Takeaways
Jack and Jill raised a $40m Series A. Air Street Capital led, with Creandum, Madrona, other funds and angels. Revenue has grown about 40 times since the $20m seed, which Creandum led. The company started in March 2025 and will keep building both products and expanding.
Two agents form a two-sided hiring marketplace. Jack, the candidate agent, serves about 350,000 people, mainly in London, San Francisco and New York. Jill, the company agent, learns what firms want and finds the best people, and works with thousands of companies.
The US is essential to winning globally. San Francisco launched at the start of 2026 and New York is on a similar path after a couple of months. Wilson says US success is fundamental to long-term and global success. The candidate side led the business side by about six weeks.
AI makes top product engineers disproportionately valuable. Agents let one engineer do work that once needed product managers, designers, QA and DevOps. This is why the minimum engineer package rose from £240,000 to £360,000 in about nine months.
Flexible pay and founder hires manage mercenary risk. Staff choose their own cash-to-equity mix, from mostly equity to mostly cash. Two thirds of the team are former founders, who Wilson says combine commercial judgement, product taste and AI engineering skill.
Talent market is bifurcating as US labs enter London. Well-funded firms, including American ones, pay more for top talent, while most of the labour market differs. Anthropic's arrival did not change Jack and Jill's approach, but the best people have options, including San Francisco.
The product is rebuilt constantly. Wilson says both agents are replatformed roughly every quarter and the offering is disrupted every three to six months. Over the next twelve to eighteen months the plan is US growth, new markets and better products.
How Jack and Jill work in practice
Jack scours every public job listing, whether or not Jack and Jill has a relationship with the employer.
Jack also gives career coaching, salary benchmarking and mock interviews.
Accelerators such as Entrepreneurs First and Antler use Jill to find potential founders in Jack's network.
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On this episode 2
Show 1
Two people met Jack, joined an accelerator and cofounded a funded company. They now use Jill to hire their first employees.