About this Founding GTM Operator SF - (Founding AE) role at Jack & Jill
What We're Building
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.
Meet Jack & Jill
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 moving at breakneck speed
We’re a year old, and already built two remarkable products, have 250,000+ candidates using Jack, thousands 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:
The Role
Two-thirds of our team are ex-founders. Matt took Omnipresent from $0 to $20M ARR in three years, then a $600M valuation. Saaras took Kular, YC-backed, from $0 to $3M ARR in twelve months. We've built at this pace in London; you'd be one of the first people building it in SF.
The immediate job is acquisition and customer expansion: get SF-headquartered companies activated on the platform. That means working rooms, running events, doing outbound, talking to founders, and converting relationships into sign-ups.
We're looking for a Founding AE to get stuck in on building our mid-market (~50-600 employees) sales motion. Over time this might evolve and change, but this is the key focus for the foreseeable future.
You're defining how we enter a market: how we sell, close, and expand. What you learn closing deals feeds back into product and builds the GTM playbook.
San Francisco is our most important market and we’re investing heavily into our motion here. We have two people on the ground today, but that’s about to change. You’ll be one of the first hires on the ground and help shape our SF GTM.
What you'll own
Full-cycle selling: prospecting, discovery, close. No BDR, no inbound handoff. You build your own pipeline.
Getting SF-headquartered companies onto the platform through outbound, events, and founder and TA relationships.
Getting new accounts to their first value moment, a role live in Jill, quickly and reliably.
Diagnosing where deals stall and fixing it, since there's no existing playbook to fall back on.
Systemising what works into repeatable pipeline, not just personal effort.
The bar
You'll be a great fit if you've carried a bag and closed at a fast-growth B2B SaaS or AI company. Not just supported deals, not just managed accounts. You prospected, ran full cycles, and hit, then beat, quota. You know what elite selling looks like because you've done it.
Beyond that:
Sharp, structured thinker who communicates with precision.
Comfortable operating with high ambiguity and zero infrastructure.
Builder instinct: you want to own a motion, not just work inside one.
SF ecosystem roots: founders and operators pick up when you call.
Nice to have
Experience selling into HR, talent, or people teams.
Time at a hypergrowth SF startup during an early scaling phase.
Founding experience, building something from nothing, even if it didn't work out.
The Process
Comp: $180k–$300k total package, flexible on cash/equity split
Location: San Francisco, hybrid in-office
Initial screen: 20 - 30 mins with Ben Norton (Ada Ventures, one of our investors)
Interview: Kaoru Fujita (hiring lead)
Day trial: In San Francisco with the broader team - Matt, Bruno, and Kaoru where schedules align
Right to work: US right to work strongly preferred. Visa sponsorship is possible in exceptional cases but will slow the process - please flag early if relevant
