Today’s best startups are building AI solutions that uplift human agency more, not less. They work to deeply understand the needs of a particular user group, documenting the most acute frustrations and challenges, and then automate the parts of the work nobody wanted to be doing in the first place. This enables users to do their best, most interesting work, and for machines to do the tedious, repetitive tasks at which they excel.
For many, job searching is a humiliating cycle of applying, ghosting, and rejection. Meanwhile, the most in-demand candidates miss out because they consider just 1% of their options.. e.g., their network or where a recruiter happened to reach out.
What’s interesting is that these experiences are two sides of the same market, and while many companies have bolted AI onto one side or the other, no startups have seen the problem holistically and built a solution for this two-sided dynamic. That is what Jack & Jill has built, and it is why Madrona is joining the company’s $40M Series A, led by Air Street Capital.
Two agents, one marketplace
Agentic AI offers a unique technological inflection point, but delivering a winning solution requires both hard engineering and genuine empathy for the candidate and the hiring team alike. Jack & Jill is a pair of AI agents, and the names are literal. Jack works for the candidate. He is an agent that learns what you want, what you’re worth, and what roles you would love to take. Jill works for the company. She learns the unsaid parts of every job description, what success in the role really looks like, and what made past hires work or fail. When the two agents agree a match is strong, the candidate is introduced directly to the hiring manager. All without a traditional application. Already, 380,000 people have had a conversation with Jack, and the two agents have arranged 25,000 interviews, with 5,000 more every month, for companies like Ramp and Attio.
We knew Jack & Jill was like no other approach when we discovered how deeply people engage with Jack. Unlike a traditional job application process that is merely a hurdle, Jack is regarded as a genuine ally in a professional’s career path. On voice calls that feel more like talking to a career coach than using a job site, candidates share things that never appear on a resume: the manager they’re trying to get away from, the salary they’re nervous to ask for, the problem they would take a pay cut to work on. One person has called Jack 144 times. No database contains that information, and nobody can scrape it.
The core insight: everyone is on the market
We love the way Matt Wilson, Jack & Jill’s CEO frames it: “every company has someone paid to represent its interests in the job market, and people have never had the same.” In addition to the benefit to the talent side of the equation this is also advantageous for the hiring companies in a foundational way: the recruiting industry has always split the world into active candidates and passive ones, and built everything for the active few. In reality, every professional sits somewhere on a spectrum, and for almost everyone there is a role, a number, or a piece of market information that would move them. The system simply never had a way to find it. An agent that knows you well enough to represent you dissolves that old binary, which means the addressable market is much larger than the fraction of LinkedIn’s 1.3 billion users actively job hunting; it’s all of them.
That is also why the consumer bet is so important. Most recruiting technology is built for the recruiter, because that is where budget is. Jack & Jill’s contrarian view is that if you win the candidate’s trust with a genuinely great consumer experience, the rest of the marketplace follows. It reflects something we look for in every AI investment. The technology alone rarely changes how a market works; everyone has access to the same models. What changes a market is AI paired with a genuinely new concept for how it can be applied and what previous market structures or categories no longer apply. Recruiting was built around the recruiter because only companies could afford a human intermediary. Once every candidate has an agent, the market looks very different.
The right team to build it
We first met Matt in December through the founders of Fyxer, who weren’t making an investor introduction so much as raving as customers. That is a great first impression when meeting a company. Matt is a third-time founder who co-founded and co-led Omnipresent through one of the most competitive corners of HR tech before its sale to Deel. Saaras Mehan, his co-founder and CTO, previously founded Kular (YC W22) and is a former England chess international, fitting for someone building matching systems. Of the company’s 25 people, 15 are former founders. They have sequenced their expansion one city at a time, from London to San Francisco in January to New York in June, and the US is already outpacing their home market.
What’s next
The professional world spent twenty years optimizing how we present ourselves to a graph but the next era is about agents that genuinely represent us within it, from first job to last, whether we’re searching or not. The result is a job market where software handles the searching and people focus on conversations about increasingly good matches for all sides. We’re glad to be building toward that alongside Matt, Saaras, and the whole Jack & Jill team.
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