The last major technological shift - the rise of the consumer internet - created LinkedIn as the networked winner in recruitment. The next great shift is here. AI is transforming how people and companies connect and it will redefine the global labor market.
At Jack & Jill, we are building the company that leads this transformation.
We’re a year old, have released two agentic products (Jack and Jill), have built a brilliant team of Europe’s best engineers, operators and ex founders, and have raised $20M, led by tier-1 VC Creandum (Lovable, Spotify, Black Forest Labs) Read more on TechCrunch.
In the coming years, every knowledge worker will have an AI agent managing their career, and every company will have an AI agent helping them hire.
By connecting those agents, we’re building a new infrastructure for the future of the labor market itself.
If that vision excites you, come help us build it.
We are not putting a thin AI layer on broken processes. We are rebuilding from first principles with two dedicated agents who work for their users:
Jack, for candidates: An always-on career co-pilot. Jack starts with a deep conversation to understand who you are and what you really want. He provides market insights, coaching, and companionship.
Jill, for companies: A true AI talent partner. Jill goes far beyond a job description to deeply understand your company, your culture, and the real context behind a role. She sources candidates, reviews inbound applicants, conducts first-pass screening calls, and acts as a strategic thought partner.
Jack & Jill will not just disrupt the existing recruitment software market, but also the 10x bigger recruitment services market.
We’re a year old, and already built two remarkable products, have 150,000+ candidates using Jack, hundreds of paying customers signed up to Jill and built a spectacular early team. The technology is ready and 10x better than the status quo – we need to build and execute at a relentless speed to build on this early momentum and bring it to the world as fast as we can.
We have thousands of users having an incredible experiences with Jack & Jill:
We're hiring Jill's second GTM hire in SF. You'll work directly alongside our US GTM Lead (Bruno), and own the market like it's your company.
This isn't a sales role with a quota and a playbook. There is no playbook. You'll write it. The question we're asking is simple: can you wake up on Monday with no instruction and identify the highest-leverage thing to do: whether that's hosting a dinner, closing a deal, pitching a VC partner, or building a channel from scratch? If the answer is no, this isn't for you.
We're an AI recruiting platform of ~20 people, most of whom are based in London (8 hours ahead). You'll be operating largely independently in SF, which means you need to be the kind of person who runs toward ambiguity, not away from it.
This is a founding role. The work will evolve as we grow.
What you'll actually do
Own the SF market end-to-end: pipeline, partnerships, events, community — whatever moves the needle
Close: run consultative sales cycles with founders, TA leads, and hiring managers at SF's best startups and scaleups
Build community and presence: host events, work the ecosystem, become the person people think of when they think of Jill in SF
Drive activation: get customers to their first value moment (a role live in Jill) quickly and reliably
Build channels from scratch: identify what doesn't exist yet and create it — VC partnerships, founder communities, referral loops
Systemise what works: turn experiments into playbooks, playbooks into compounding flywheels
You're a genuine 0→1 builder with commercial instincts. You don't need a defined remit to operate at full speed. You have deep roots in the SF startup ecosystem and know how to work a room — but you can also run a structured sales cycle and close.
Beyond that:
High agency: you create your own to-do list, not someone else's
Spiky, not well-rounded — you have an outlier strength and you know what it is
Comfortable operating with minimal oversight in a fast-changing environment
SF-based, right to work in the US
We're looking for spikiness, not uniformity. We want complementary strengths — not duplicates of what the existing team already brings. Strong fits look like:
The TA/recruiting background turned closer: You've lived inside the hiring market — placed candidates, managed client relationships, understood the buyer deeply — and you've since proven you can sell and close. You bring buyer credibility no pure AE can replicate.
The marketplace or GTM operator: You've built something at a company like Brex, Deel, or Stripe — community-led growth, supply/demand flywheels, new market expansion. You know how to build from zero, not just scale what exists.
The ecosystem builder: You have deep SF relationships across founders, VCs, and operators. You can walk into any room and leave with pipeline. You're as comfortable pitching a partner at a top-tier fund as you are closing a Series A founder.
The ex-founder with commercial instincts: You've built something, developed strong GTM intuition, and now you want to bring that energy to a fast-growing AI company at an inflection point.
Founded by two experienced serial founders
Matt (CEO) - previous company grew to a $600m valuation in 3 years before exiting to Deel
Saaras (CTO) went 0→ $3m ARR in a year as founder/CTO YC AI sales startup Kular.ai
We’re a 20-person, founder-heavy team (10+ ex-founders)
Check out our full team here
We’re building a high-performance environment. You’ll work hard, and we want to clear your plate to make sure that you have everything you need to be able to perform at your very best!
💰 Total Compensation for this role of $180-300k (we let you choose your cash : equity split)
🏥 Private health insurance
🚗 Uber home if you’re working late
🍲 Doordash dinners in the office
✈️ Periodic trips to London
🧽 Fortnightly
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