Jack & Jill secured a $40M Series A led by Air Street Capital, elevating total funding to $60M and fueling expansion of its dual AI agents that match candidates and employers through mutual fit introductions.
Jack & Jill raised $40 million in a Series A led by Air Street Capital (Nathan Benaich), bringing total funding to approximately $60 million less than a year after its $20 million seed round. New investors include Madrona and Antler; returning backers include Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital, and Repeat.vc. PitchBook lists the Series A at roughly $40.7 million, with the company founded in 2025 and still early stage/generating revenue.
The San Francisco and London-based company builds dual conversational AI agents that sit on opposite sides of the hiring market and only introduce parties when both sides signal mutual fit. Jack acts for candidates: it learns preferences, background, and career goals through voice calls, email, and WhatsApp (users have logged thousands of hours of conversation), scans large volumes of jobs, offers coaching and mock interviews, and seeks direct introductions rather than traditional applications. Jill acts for employers: it digests job descriptions, probes hiring managers on what true success in the role looks like, and surfaces high signal candidates from Jack’s network. When the agents agree, the candidate meets the hiring manager directly, skipping applications. The company is paid by employers and only upon successful hires; Jack remains free for candidates.
Since the October 2025 seed (when Jack had spoken with ~49–50k candidates and Jill served hundreds of companies), metrics have scaled sharply:
- Jack’s network: ~350,000 people (roughly 10× growth).
- Jill: used by ~5,000 businesses, including Ramp, Attio, Multiverse, Corgi, Tavus, Faculty, and Fyxer.
- Interviews arranged: 25,000 cumulative, now running at ~5,000 per month.
- Website counters at the time of reporting showed thousands of companies on Jill, hundreds of thousands of professionals on Jack, and over 100 million job matches reviewed.
- Revenue is described as having increased substantially (one report cites a 40-fold rise since seed, though from a low base). American interview volume is reported as nearly 4× the London rate over comparable post launch periods. Engagement depth is notable: recent months alone saw ~12,000 hours of calls with Jack, including extreme cases of individual users logging dozens of hours.
The team has grown to ~29 people across London and San Francisco (earlier PitchBook snapshots listed far fewer), with open roles emphasizing high talent density hiring in engineering, GTM, and operations. Co-founders are Matthew Wilson (CEO; previously founded Omnipresent, the employer of record platform later acquired by Deel) and Saaras Mehan (CTO; previously of Kular.ai). The culture emphasizes in-office work, rapid shipping with heavy use of agents, and ownership.
Air Street Capital’s lead (Benaich) frames the opportunity as moving beyond better search or automated outreach over static resumes: “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.” Wilson emphasizes the asymmetry: companies have always paid representatives in the talent market; individuals have not. The dual agent design aims to realign incentives that traditional agencies and job boards often fail to solve, reducing noise while capturing richer, non scrapable context (manager preferences, salary sensitivities, problem domains people care about).
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This sits in a broader wave of agentic AI applied to recruitment and matching. Competitors and adjacent players pursue voice agents, expert matching, or screening tools; Jack & Jill differentiates by running parallel agents that negotiate introductions rather than purely filtering or ranking. Early seed investors (Creandum as lead, plus Dig Ventures, Ada, EF, angels from Anthropic/ElevenLabs/Lovable and others) already backed the thesis of high early traction validating demand for agentic recruitment.
The $40M extends runway for product depth (richer multi channel conversations, better matching/negotiation logic), geographic expansion (particularly the US, where traction is accelerating), team growth, and scaling the two sided network. Unit economics benefit from a success fee model tied to hires rather than pure SaaS seats or per application fees. The absence of disclosed hire conversion rates from the 25,000 interviews leaves the ultimate efficiency claim open, but the combination of network scale, interview volume, and reported revenue growth indicates strong early product market fit in high growth tech and related verticals.
Regulatory considerations in Europe (high risk classification under the EU AI Act for recruitment systems, transparency duties already in force for AI interactions, GDPR automated decision rules) form part of the operating environment; the company has not publicly detailed its compliance approach in the funding announcement. Overall, the round positions Jack & Jill as a well capitalized player attempting to rebuild the matching layer of the labor market around persistent, preference aware agents rather than static listings or human intermediaries alone.
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