Jack & Jill has raised $40 million in Series A funding to expand its AI-powered hiring marketplace, where separate AI agents represent job seekers and employers and introduce candidates directly to hiring decision-makers without requiring a traditional job application. Air Street Capital led the financing, with participation from new investors Madrona and Antler. Existing investors Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc also participated.
The round brings Jack & Jill’s total funding to $60 million just 10 months after the company raised a $20 million seed round led by Creandum.
Other investors in the company include Dig Ventures, Firedrop, Episode 1 and Playfair.
Jack & Jill was founded around two AI agents designed to represent opposite sides of the job market.
Jack works for individuals considering their next career move, while Jill works for companies looking to hire.
Instead of having candidates search job boards, complete applications and wait for recruiting teams to respond, Jack develops an understanding of what each person wants from their career.
Jill separately develops an understanding of what an employer actually needs from a particular hire.
When the two agents determine that the person and position are a strong match, the candidate can be introduced directly to the hiring manager or other decision-maker.
The company is attempting to build a job marketplace in which the initial application process largely disappears and opportunities are discovered through agents acting continuously on behalf of both candidates and employers.
Jack’s network has grown to approximately 350,000 people, representing a tenfold increase since the company’s seed financing.
Jill has worked with approximately 5,000 businesses, including Ramp, Attio, Multiverse, Corgi, Tavus, Faculty and Fyxer.
The platform has facilitated approximately 25,000 interviews without candidates submitting traditional applications.
Jack & Jill is now arranging approximately 5,000 additional interviews every month.
Revenue has increased approximately 40-fold since the seed round.
The company’s early U.S. expansion has also progressed faster than its original London launch.
Jack & Jill entered San Francisco in January 2026 and New York in June.
Over comparable periods following launch, the company said San Francisco and New York generated nearly four times as many interviews as London.
The new financing will help Jack & Jill continue expanding across the United States.
The company believes the traditional online hiring model is becoming less effective as artificial intelligence makes it easier for candidates to submit applications and for employers to automate recruiting outreach.
That creates a volume problem on both sides.
Candidates can apply to far more jobs, but employers receive larger applicant pools that may contain relatively little information about which candidates are genuinely interested.
Employers can simultaneously send significantly more automated recruiting messages, making it harder for candidates to determine which opportunities are actually relevant.
Jack & Jill’s model attempts to replace that volume-driven process with richer information gathered by AI agents.
Professionals interact with Jack through voice conversations similar to sessions with a career coach.
Rather than relying only on a résumé or professional profile, Jack can learn about factors that might substantially affect whether someone would consider changing jobs.
Those conversations can include compensation expectations, management preferences, career frustrations, preferred types of work and longer-term ambitions.
Users have spent approximately 12,000 hours speaking with Jack during the past several months.
One user has called the agent 144 times and accumulated approximately 44 hours of conversations.
Many users return weekly and continue the same career conversation over several months.
The company sees those interactions as an important data advantage because much of what professionals tell Jack would not normally appear on a résumé, LinkedIn profile or conventional recruiting database.
For example, someone could tell Jack about a manager they want to leave, compensation they are hesitant to request or a type of problem they would accept lower pay to work on.
Jack can also benchmark compensation, help users think through counteroffers and discuss possible career directions when they are uncertain about their next move.
In the background, the agent searches millions of open positions and attempts to surface only opportunities that align closely with what the individual has described.
Jack & Jill believes that model creates a richer candidate profile than systems primarily matching people and jobs through résumé keywords.
Jill performs a corresponding role for employers.
The agent analyzes a company’s job description, researches the organization, and asks additional questions intended to determine what success in the role actually looks like.
Jill then searches Jack’s network for potential candidates.
Because individuals in the network may already have extensive conversations, emails or WhatsApp interactions with Jack, the platform can use significantly more context when evaluating potential matches.
That allows Jack and Jill to consider interests, motivations, preferences and career objectives that may not be visible through a conventional résumé.
When both agents determine there is sufficient alignment, they can make an introduction.
Jack & Jill compares the model with executive recruiting, where a recruiter develops a detailed understanding of both the candidate and employer and brokers introductions rather than simply collecting applications.
The company is attempting to make that type of personalized representation available at much larger scale through AI.
Its founders believe AI agents will eventually represent a significant portion of both workers and employers throughout the job market.
Jack & Jill CEO and Co-Founder Matt Wilson predicts that by 2030 as many as one billion people could have an AI agent continuously searching opportunities on their behalf.
On the employer side, companies could similarly operate AI agents that continually evaluate candidates and initiate conversations when appropriate.
Connecting those systems could potentially create a job market where opportunities are identified automatically rather than requiring individuals to repeatedly search and apply.
The company was founded in March 2025 by Wilson and CTO Saaras Mehan.
Wilson previously co-founded and co-led employer-of-record company Omnipresent, helping grow the business globally before its acquisition by Deel in 2025.
Mehan previously co-founded Y Combinator-backed Kular and is a former England chess international.
Jack & Jill currently employs 25 people across London and San Francisco.
Fifteen members of the team are former founders.
The Series A follows the company’s $20 million seed financing completed in October 2025.
That round was led by Creandum and included more than 75 angel investors, including former Formula One driver Nico Rosberg and individuals associated with companies including Lovable, Anthropic and ElevenLabs.
Air Street Capital led the new round around the thesis that the next major change in recruiting will come not from improving search across existing résumé databases, but from placing intelligent agents on both sides of the employment marketplace.
The investor also highlighted the proprietary information candidates voluntarily share with Jack as a potential competitive advantage.
That information is not readily available through traditional professional databases because it reflects private conversations about what individuals actually want from their careers.
Jack & Jill intends to use the new capital to expand that network while increasing adoption of Jill among employers.
The company’s longer-term goal is to shift hiring away from applications and toward continuous matching between agents that understand both sides of the employment decision.
KEY QUOTES:
“The next leap in hiring will not come from better searches over the same resumes or more automated outreach. It will come from putting an agent on both sides of the table and making the introduction only when both sides would take the call.”
“Hundreds of thousands of people have told Jack, in their own words, what they want from their careers. No database contains that information and nobody can scrape it. We led this round because Matt and Saaras are rebuilding the market rather than building another tool to search it.”
Nathan Benaich, General Partner at Air Street Capital
“AI is displacing jobs and pushing more people into the job market. At the same time, automated applications and outreach are flooding inboxes and applicant pools. Candidates struggle to be seen, while employers cannot tell who is serious. More applications and better filters will not solve that. It requires a fundamentally different solution: a marketplace brokered by agents that understand what both sides want.”
Saaras Mehan, Co-Founder and CTO of Jack & Jill
“Every company has someone paid to represent its interests in the job market. People have never had the same for their careers. By 2030, a billion people will have an AI agent searching every opportunity on their behalf and deciding which ones deserve their attention. Every company will have one helping it hire. Connecting those agents will make the job market run like clockwork and uncover opportunities on both sides that would otherwise be missed.”
Matt Wilson, Co-Founder and CEO of Jack & Jill
“Jill gives us exactly what we need. Direct introductions to people we want to hire, not another shortlist. Within minutes of briefing her on a role, I have meetings with strong candidates in my calendar.”
Archie Hollingsworth, Co-Founder of Fyxer
“I wanted to spend my time building AI projects I was genuinely excited about, not searching for jobs. Jack unlocked that for me. He searched the market on my behalf and, within a week of our first conversation, introduced me to a pre-seed accelerator. It opened up a path to becoming a founder that I did not even know existed.”
Michael Hurley, Jack User
