Jack & Jill raises $40M to replace job applications with agent introductions

Why it matters

Air Street is backing agent-to-agent matching as a new marketplace layer. Jack & Jill must now prove its conversations convert into hires, a figure it has not disclosed.

Matthew Wilson and Saaras Mehan have raised a $40 million Series A for Jack & Jill, their bet that job seekers and hiring managers should each send an AI agent to negotiate the first introduction.

Jack & Jill announced the financing on September 15th, with Air Street Capital leading and existing investor Creandum participating alongside Madrona. Antler joined the round, while Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc returned, according to independent reporting. The financing brings Jack & Jill's reported total funding to $60 million, following a $20 million seed led by Creandum in October 2025. Jack & Jill did not disclose a valuation.

Wilson, Jack & Jill's CEO, arrived at recruitment software after building infrastructure for international employment. He previously co-founded Omnipresent, an employer-of-record platform that helped companies employ workers across borders and was later acquired by Deel. That experience gave Wilson a close view of how companies search for talent, particularly when the suitable candidate may live in another city or country.

Mehan, Jack & Jill's CTO, studied computer science at Cambridge and previously worked at Autodesk Research, Goldman Sachs and Microsoft Research. He later co-founded Kular, an AI sales startup that joined Y Combinator's Winter 2022 batch. His argument for Jack & Jill, as stated in the Series A announcement, is that another layer of application filters will preserve the central failure in online hiring: employers cannot identify serious candidates, while qualified candidates struggle to get seen.

Two agents, one introduction

Jack & Jill splits the recruitment process between two products. Jack holds voice conversations with professionals about their experience, ambitions and constraints, then searches for relevant openings. Jack also offers interview preparation, salary benchmarking, career coaching and negotiation support.

Jill works for hiring managers. Employers brief the agent on a role, and Jill searches the candidate network assembled through Jack. When the two systems find mutual interest, Jack & Jill introduces the candidate and employer directly, bypassing the conventional application queue.

That structure turns the product into a marketplace rather than a standalone recruiting assistant. Jack needs enough professionals to give Jill useful coverage, while Jill needs enough active roles to make Jack valuable to candidates. Each side can deliver a useful service independently, but the defensible asset Wilson and Mehan are trying to build is the network between them.

Candidates use Jack for free. Jack & Jill says employers pay only after making a hire, aligning its revenue with completed placements rather than applications, messages or software seats. Jack & Jill also says Jack scans 15 million jobs a day. Those figures are company-supplied and lack an accompanying methodology.

Jack & Jill says 380,000 people in San Francisco, New York and London have spoken with Jack. The company also says over 5,000 companies are hiring through Jill, including Ramp, Multiverse, Maze, Corgi and Attio. Jack & Jill has not published revenue, completed-hire volume or the conversion rate from introductions to employment, leaving the marketplace's economic performance harder to judge than its top-of-funnel growth.

Wilson is building for density this time

Wilson's previous company sold the infrastructure required after a business had decided whom to employ. Jack & Jill moves him earlier in the transaction, into the decision over which candidate and company should meet in the first place.

That is a larger market and a harder marketplace problem. Recruiting platforms have spent years accumulating resumes, professional profiles and employer demand. AI has also reduced the cost of submitting applications and contacting candidates, creating larger pools of activity without necessarily creating better matches. When Wilson launched Jack & Jill's seed round, he described job listings drawing hundreds of applications within hours, sometimes producing a queue that employers never fully reviewed.

Wilson and Mehan are using conversation as the filter. A voice agent can ask candidates about motivations, trade-offs and ambitions that fit awkwardly into a resume. An employer-side agent can press a hiring manager on what success in a role actually requires. The resulting introduction carries information gathered from both parties, rather than matching a job description against a profile full of keywords.

Creandum backed that model at seed, citing Wilson's experience building Omnipresent and Mehan's work at Kular. Air Street's decision to lead the Series A pushes the thesis further: the venture firm is backing agent-to-agent coordination as the marketplace layer, rather than treating AI as another screening feature inside existing recruitment software.

The US expansion raises the stakes

Jack & Jill operates and lists company openings in London and San Francisco. The founders said the Series A will help Jack & Jill move faster toward broader coverage, with the US expansion central to the next phase.

The new capital arrives less than a year after the seed round, a compressed fundraising cycle that reflects both Jack & Jill's reported user growth and investors' appetite for AI systems that perform work across existing software categories. The $40 million round gives Wilson and Mehan room to acquire candidates and employers in parallel, an expensive requirement for any two-sided network.

It also creates a clear test. Recruitment software already includes AI sourcing, interviewing and candidate-ranking products, while established platforms are adding similar functions. Jack & Jill's distinction rests on representing both parties and waiting for mutual interest before making an introduction. That distinction will matter only if the network produces hires consistently enough for employers to pay and candidates to keep their agents active.

Wilson has already built a company around the complications that follow a hire. With Jack & Jill, he and Mehan are spending $40 million to own the introduction that comes before it.