Jack & Jill
Entrepreneur First '25London, GB · Founded 2025 · 20 employees · 12 known investors
Jack & Jill builds AI agents to support job seekers and companies in hiring: Jack helps individuals navigate career transitions and job searches with personalized coaching, while Jill assists companies in identifying and recruiting qualified candidates. The platform aims to make career management and recruitment more accessible and efficient through artificial intelligence.
Also known as Jack and Jill · jackandjill.ai
Founders & leadership
Jack & Jill was founded in 2025 by Matthew Wilson, Saaras Mehan, and Matt Wilson.
Investors · 12
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Also in the syndicate · 6
Company profile
researched Aug 2026Jack & Jill is a London-based recruitment technology company that operates a two-sided platform built around conversational AI agents. The candidate-facing agent, Jack, conducts a structured interview with a job seeker (described by the company as roughly 10 minutes and by press coverage as a 20-minute profile interview) to understand skills, experience and career goals, then scans job listings daily and returns curated matches. Jack also provides mock interviews with feedback, salary benchmarking, salary-negotiation coaching, CV feedback and general career-clarity coaching. The employer-facing agent, Jill, works with hiring teams to build a profile of an open role and surfaces and elevates matching candidates, functioning as a digital headhunter over the candidate network generated by Jack's conversations.
When Jack identifies a candidate that fits a role within Jill's network, the platform makes a direct introduction to the hiring manager rather than routing the candidate through a conventional application. Both agents are described as autonomous and capable of holding many simultaneous conversations, which the founders frame as delivering recruiter-style service at lower cost. The company positions the product against the volume problem of mainstream job boards, citing cases where a LinkedIn posting can attract 1,000 applicants within six hours and where employers do not review the resulting applications.
The company's website states that 355,922 professionals work with Jack, that 15 million jobs are scanned daily, and that users save an average of 30 hours versus a traditional job search. At the time of its October 2025 funding announcement, reported traction was nearly 50,000 users/candidate conversations in London and hundreds of hiring teams using Jill.
Founding story
Founded in 2025 (described by Sifted in October 2025 as roughly six months old) by Matthew (Matt) Wilson, a London-based serial entrepreneur and founder of HR tech scaleup Omnipresent, and Saaras Mehan, the Y Combinator-backed founder of Kular.ai. Wilson has framed the motivation as the inefficiency of how people are matched to employers and the low signal-to-noise ratio of high-volume online applications.
Business model
Two-sided marketplace: the candidate product (Jack) is free to job seekers, while employers pay when they hire through the employer-side agent (Jill). Press coverage describes this as a standard commission on any successful hire.
Placement/success fees charged to employers when a hire is made through Jill; no subscription or fee charged to candidates, whose plan is listed at $0 per month with all features included.
Traction
Website figures: 355,922 professionals using Jack, 15 million jobs scanned daily, an average 30 hours saved per job search. At the October 2025 seed announcement the company reported nearly 50,000 users / over 49,000 candidate conversations, with service live in London and hundreds of hiring teams using Jill, including TrueLayer. Public testimonials name users placed at companies such as Marloo and interviews arranged with Antler.
Latest developments
The most recent reported development is the October 2025 $20 million seed round led by Creandum with participation from Ada Ventures, DIG Ventures, Entrepreneur First, Firedrop, Repeat.vc, Episode1 Ventures, Playfair and over 75 angels including Nico Rosberg and individuals from Lovable, Anthropic and ElevenLabs, earmarked for US expansion and platform development. The company website currently advertises the seed round and reports 355,922 professionals using Jack.
▸Full profile — market position, technology, go-to-market, geography, history, risks & controversies
Market position
Positions itself as an alternative to incumbent job boards and professional networks such as LinkedIn and Indeed, which the CEO says have not fundamentally changed job search in 20 years, and as an agentic AI replacement for parts of the human recruiter workflow. Creandum described the company as one of the most exciting businesses applying agentic AI it had seen, citing early market traction.
Uses chatbot-based interviews on both sides of the market rather than keyword matching or resume screening, and replaces applications with direct introductions to hiring managers. The candidate side is free, with monetisation shifted entirely to employers; the company also emphasises access to roles at early-stage companies that are not posted publicly and candidate control over what information is shared.
Technology
Conversational AI agents that conduct structured voice/chat interviews with candidates and hiring teams, a daily job-scanning pipeline covering a stated 15 million jobs, matching logic that scores candidate-role fit, and feedback tooling such as mock-interview confidence scoring and salary benchmarking derived from job data. The platform continuously analyses conversation data to refine matching and recommendations.
Go-to-market
Direct consumer sign-up for the free Jack agent, with candidate volume creating the talent network that makes Jill valuable to employer customers; a referral page exists on the site. Media coverage of the seed round and use of the funding for marketing support growth, alongside geographic expansion into the US (San Francisco) and Europe.
Two groups: individual professionals seeking new roles (website examples skew to engineering, product and marketing roles in London, remote and San Francisco), and hiring teams at fast-growing and high-growth companies, initially in London.
Geography
Headquartered and initially operating in London, UK, with the candidate product also surfacing roles in remote and US locations such as San Francisco. Announced plans to open US operations in San Francisco and, per one report, expand across Europe.
History
Established in 2025 in London; the service launched in London and was already live and generating users before its funding announcement rather than operating in stealth. On 16 October 2025 the company announced a $20 million seed round led by Creandum, intended to fund US expansion (including a San Francisco presence), team growth, product development and marketing.
Risks & controversies
Reported user and traction figures come largely from the company itself and vary between sources (nearly 50,000 users in London at the October 2025 announcement versus 355,922 professionals shown on the website), and the candidate interview length is described as 10 minutes on the website but 20 minutes in press coverage. Coverage notes that AI-conducted first-round interviews can feel alienating to candidates, and that the broader market suffers from AI-generated mass applications and fake applicants. TechCrunch also published a correction after an erroneous figure appeared in its original headline.
Compiled by commissioned research from 8 cited public sources — announcements, filings, and press listed under research sources below.
Key figures
latest reportedCompany-reported or press-reported figures, each dated to when it was claimed — not independently audited.
Founder mafia
4 people who came through Jack & Jill went on to found or lead other companies.
Competitors · 1
by search overlapCompanies competing with Jack & Jill for the same Google search keywords, organic and paid, via search-intersection analysis.
Timeline · 3
launches, deals, and filingsThe company announced a $20 million seed round led by Creandum, with participation from Ada Ventures, DIG Ventures, Entrepreneur First, Firedrop, Repeat.vc, Episode1 Ventures, Playfair and more than 75 angel investors, including Nico Rosberg and people from Lovable, Anthropic and ElevenLabs. Proceeds are earmarked for US expansion (including establishing operations in San Francisco), team growth and product development.
$20M source ↗
Sifted reported that hundreds of fast-growing companies use Jill within their hiring teams, including open banking platform TrueLayer.
Following the seed round, the company said it would use the capital to fund a US expansion, including establishing operations in San Francisco and scaling its platform for the US market; Sifted also reported European expansion plans.
Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.
▸Research sources · 8
primary sources listed
- Jack & Jilljackandjill.ai · web
8 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does Jack & Jill do?
- London-based startup running two conversational AI agents — Jack for job seekers and Jill for employers — across the hiring process.
- Who founded Jack & Jill?
- Jack & Jill was founded by Matthew Wilson, Saaras Mehan, Matt Wilson in 2025.
- Who are Jack & Jill's investors?
- Jack & Jill's investors include Creandum, Dig Ventures Management Limited, Entrepreneur First, Episode1, Playfair Capital, Ada Ventures.
- Where is Jack & Jill headquartered?
- Jack & Jill is headquartered in London, GB.