--- title: 'Founding Operator (£100-£150k+) at Jack & Jill' canonical: 'https://feeny.ai/job/founding-operator-100-150k-jack-jill-london-6vhqwc28v6h6' type: 'job' last_seen: '2026-09-08' --- # Founding Operator (£100-£150k+) at Jack & Jill - **Company:** Jack & Jill - **Location:** London, United Kingdom - **Employment:** full-time - **Work type:** onsite - **Posted:** 2026-09-04 - **Last confirmed live:** 2026-09-08 - **Apply:** https://jobs.ashbyhq.com/jack-jill-external-ats/5ad034cc-1bcb-4e47-a16b-7d49f82e2fc7 ## Job description 👋 WHAT ARE WE 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 labour market. At Jack & Jill, we are building the company that leads this transformation. We're 17 months old, and have built a brilliant team of Europe's best engineers, operators and ex-founders. We are run-rating multiple £xm in revenue, and have raised $20M led by tier 1 VC Creandum (Lovable, Spotify, Black Forest Labs, Bolt). Read more on TechCrunch. https://techcrunch.com/2025/10/16/jack-jill-raises-20-million-to-bring-conversational-ai-to-job-hunting/ 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 labour market itself. If that vision excites you, come help us build it. 👀 WHAT IS THE ROLE AND WHO ARE WE LOOKING FOR? We're hiring a Founding Operator to join our Jill Delivery team, working alongside Ed Steele https://www.linkedin.com/in/ed-steele/ and Ed Kim https://www.linkedin.com/in/edkbh/. You’ll take the initiative on reaching out, building relationships and closely supporting our existing customers. Hundreds of companies have now set a role via Jill. We want to hire someone who wakes up thinking about which customers they're going to talk to today, rather than waiting for a ticket, a QBR or a scheduled check-in. This is a 0→1 role and relentlessly customer-facing. You'll be on calls, in Slack channels, in inboxes and sometimes visiting offices. You'll learn how to support and expand individual customers, and then you'll go and make it happen across our entire base. What you'll actually do: - Constantly get in front of existing customers. You'll set the pace: reaching out, opening conversations, support closely and gathering detailed feedback. You’ll care deeply about the quality of our customer experience. - Own the relationships. Be the trusted point of contact for a portfolio of customers. Spot risk early, handle escalations calmly, and build partnerships where customers come to you before they think about leaving. - Drive adoption and outcomes. Make sure customers are getting real value: roles filled, time saved, hiring managers who feel genuinely supported by Jill. - Drive expansion - this is a commercial role. When a customer sees value, your job is to make sure the next role goes in immediately. You'll be accountable for growing revenue from existing accounts, not just protecting it. - Own customer delivery workstreams. You could improve customer enablement in-product, build agents to automate workflows, or work closely with our engineers to A/B test new features. We value team members who wear multiple hats. - Be the voice of the customer. You'll be closer to customer reality than almost anyone. Feed sharp, structured insight back to our engineers so we keep building the right things. ## YOU'LL BE A GREAT FIT IF 🧭 You're high agency with a real bias to action. You'd rather send messages today than design the perfect campaign for next week. You don't wait to be told who to call. 📞 You genuinely like talking to customers. You're energised by a day of back-to-back conversations and you're comfortable picking up the phone to someone who's gone quiet. 🏢 You've been part of hiring processes. You understand what it's like to be a hiring manager: the anxiety of a role sitting open too long, what a great candidate brief looks like, and why speed and communication matter so much. That gives you genuine empathy for our customers. 🤝 You have partnerships, account management or CS/CX experience. You've owned a book of business before. You know how to build trust, manage expectations, and turn initial value into long-term retention and expansion. 🎓 You're sharp and structured. You think clearly under ambiguity, communicate with precision, and can hold a complex customer situation in your head while still moving fast. 💻 You have some technical chops. You don't need to be an engineer, but if you can hack together a script or hold your own in a technical conversation, you'll be significantly more effective. You use AI properly, as a genuine force multiplier. ## THE PROFILE We're open to exceptional people from a range of backgrounds, but you likely fit one of these: - The Relationship-Led Operator: You've worked in a partnerships-type role and grown a book of business through sheer force of contact - calls made, relationships built, accounts expanded. You measure yourself on customer outcomes, not activity dashboards. - The Ex-Founder: You've built something before, worn every hat, spent your days selling and supporting, and are ready to go 0→1 again in a high-ownership role at a rocketship. - The Systems-Minded CS Operator: You've come from CS/CX and you’ve built genuinely complex, intelligent systems behind your customer work. You’re relatively technical and very high-velocity in managing customer relationships at scale. ## THIS ROLE ISN'T FOR YOU IF 🖥️ You want a predictable 9-to-5. We're building fast and the work is intense. We respect life outside of work, but we do what it takes to win. 🎧 You'd rather work asynchronously. This role lives in conversations. If your instinct is to build the system before speaking to anyone, you'll be happier in a different role. 🧱 You need a highly structured environment. We're in the ambiguous, thrilling phase of 0-to-1. You'll be creating the structure, not operating within it. ⚙️ You want to jump straight into leading a team. This is primarily a hands-on IC role. The opportunity to grow is real, but you need to earn it by doing first. ## 🏋🏻‍♀️ OUR TEAM 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 http://Kular.ai You'll be working closely alongside exceptional commercial leaders. - Ed Steele (Founding Operator, Jill Delivery) - Ex-founder & COO of Hoxton Farms. Raised $30m. ex-Thought Machine. - K Fujita (Jill GTM Lead) - 2x $0-25m, 2x exits, 2x $0-1m, ex VP Sales/Marketing Omnipresent, ex Entrepreneur First Founder. We're a 25-person, founder-heavy team (17 ex-founders) Check out our full team here https://www.jackandjill.ai/about-us. ## 🎁 AND THERE'S ALSO THE PERKS… We're building a high-performance environment. You'll work hard, and we want to clear your plate so you can perform at your very best. 💰 Total Compensation for this role of £100-150k+ (we let you choose your cash : equity split) 🏥 Private health insurance with Bupa 🚗 An Uber home if you're working late 🍲 Deliveroo dinners in the office 🧽 Fortnightly home clean 💻 Brand new MacBook 📍 In-person, 5 days a week at our London office in Shoreditch Exchange, surrounded by builders. 📌 HOW DO I JOIN THE JOURNEY? How to Apply: - Submit via our application form - we'll ask you to speak to Jack about your experience and what's next. If it's a fit, we'll follow up via email. - Intro call with our team. - Paid work trial - a working session with the team. We'll give you a real problem we're facing today and work through it together. - Offer, referencing & start ## About Jack & Jill ## Company Overview - **One-liner**: Jack & Jill is an AI hiring platform that uses two complementary AI agents—Jack for candidates and Jill for companies—to connect pre-vetted professionals with opportunities at startups. - **Entity Type**: Private (Seed stage; raised $20M Seed round) - **Headquarters**: London, UK; with a San Francisco office for the US market - **Founded**: 2024 - **Founders**: Matthew Wilson (CEO), Saaras Mehan (CTO), and Carla L [tracxn.com](https://tracxn.com/d/companies/jackjillai/__wLcwVwws4k1gNMZOig9YJQ2ERxniHFBUBezcJQ0ShIw) ## Core Business - **Primary industry**: AI-powered recruitment / talent acquisition - **Target customers**: B2B (employers – Seed-to-Series-C startups) and B2C (job seekers – professionals in engineering, marketing, sales, operations, design, product, and leadership) - **Mission or purpose**: “Introduce remarkable people to remarkable companies” – solving the inefficiency in the job market by using conversational AI to replace traditional job boards and agency recruiting [jackandjill.ai](https://jackandjill.ai/) ## Products & Services - **Jack** – A free AI career agent for candidates. Jack scans 15 million jobs daily, conducts mock interviews, benchmarks salary, provides career-clarity coaching, and introduces candidates directly to hiring managers. Jack is fiduciary to the candidate and never works for companies. [jackandjill.ai](https://jackandjill.ai/) - **Jill** – An AI recruiter for companies. After a hiring team briefs Jill on a role, Jill returns a curated shortlist of candidates from Jack’s network within minutes. Jill handles outreach, scheduling, and pipeline management, and integrates with Ashby ATS. [jackandjill.ai](https://jackandjill.ai/) - **Additional candidate tools**: Salary Benchmark, Mock Interviews, Career Clarity Coaching, Job Description Compare, and Hiring Salary Estimator [jackandjill.ai/about-us](https://jackandjill.ai/about-us) ## Market Standing - **Valuation/Market Cap**: Not disclosed (private, seed-stage) - **Key Metric**: Total Funding – $20M Seed round (October 2025) [techcrunch.com](https://techcrunch.com/2025/10/16/jack-jill-raises-20-million-to-bring-conversational-ai-to-job-hunting/) - **Notable Investors/Partners**: Lead investor Creandum (backed Spotify, Klarna, Bolt) [techcrunch.com](https://techcrunch.com/2025/10/16/jack-jill-raises-20-million-to-bring-conversational-ai-to-job-hunting/) - **Growth Signals**: - Network of 281,466 pre-vetted professionals (as of mid-2026) [jackandjill.ai](https://jackandjill.ai/) - 2,000+ Seed-to-Series-C startup customers in London, San Francisco, and New York [jackandjill.ai](https://jackandjill.ai/) - Headcount grew ~1,500% year-over-year to 29 employees (LinkedIn data) [linkedin.com](https://www.linkedin.com/company/jackandjillai) - 494 active job postings, with monthly posting growth of +128.7% [linkedin.com](https://www.linkedin.com/company/jackandjillai) ## Competitive Advantages - **Dual‑agent model**: Jack builds and maintains a trusted candidate network; Jill matches that network to live roles. No conflict of interest because Jack never works for employers and Jill never cold-messages strangers. [jackandjill.ai](https://jackandjill.ai/) - **Speed and cost**: Shortlists delivered within minutes; 10% success fee vs. 20–30% for traditional agencies, with a 3-month full-refund guarantee. No retainers or minimum commitments. [jackandjill.ai](https://jackandjill.ai/) - **Algorithmic fairness**: Published a 2026 Guide to Bias in AI Recruitment, demonstrating a commitment to reducing bias in hiring decisions. [jackandjill.ai](https://jackandjill.ai/) - **Candidate-first design**: Every candidate has a real conversation with Jack (about 500/day) and opts in before being presented to companies, resulting in higher-intent matches. ## Strategic Focus - **US market expansion**: After launching in London, the seed funding is fueling a push into San Francisco/Bay Area and New York, with a dedicated US GTM team [techcrunch.com](https://techcrunch.com/2025/10/16/jack-jill-raises-20-million-to-bring-conversational-ai-to-job-hunting/) - **Product depth**: Continuing to enhance Jack’s coaching and mock interview capabilities, and refining Jill’s matching and integration (e.g., bidirectional Ashby ATS sync) [jackandjill.ai](https://jackandjill.ai/) - **Category creation**: Aiming to become the default hiring infrastructure for startups, displacing traditional agencies and legacy job boards [techcrunch.com](https://techcrunch.com/2025/10/16/jack-jill-raises-20-million-to-bring-conversational-ai-to-job-hunting/) ## Why Work Here - **High-growth startup**: Headcount growing rapidly (1,500% YoY), offering early‑stage impact and career acceleration [linkedin.com](https://www.linkedin.com/company/jackandjillai) - **Mission-driven**: Solving a real pain point in the job market with AI that aims to be fair, transparent, and candidate-friendly. - **Culture & team**: Small but growing team of ~29 with founding leads in growth, GTM, design, and marketing. Office presence in London, San Francisco, and New York. Remote/hybrid policy not publicly detailed but likely flexible given distributed US/UK operations. - **Notable perks**: Free candidate tools (salary benchmarking, mock interviews) available to employees; equity in a well-funded seed-stage company with top-tier investors like Creandum. - **Engineering focus**: Building AI agents at scale, with opportunities to work on NLP, bias mitigation, and real-time matching systems. ## Sources 1. [jackandjill.ai - Homepage](https://jackandjill.ai/) 2. [jackandjill.ai - About Us](https://jackandjill.ai/about-us) 3. [techcrunch.com - Jack & Jill raises $20M](https://techcrunch.com/2025/10/16/jack-jill-raises-20-million-to-bring-conversational-ai-to-job-hunting/) 4. [linkedin.com - Jack & Jill company page](https://www.linkedin.com/company/jackandjillai) 5. [tracxn.com - Jack & Jill profile](https://tracxn.com/d/companies/jackjillai/__wLcwVwws4k1gNMZOig9YJQ2ERxniHFBUBezcJQ0ShIw) 6. [jobs.ashbyhq.com - Jack & Jill careers page](https://jobs.ashbyhq.com/jack-jill-external-ats) ## Other roles at Jack & Jill - [Founding Community and Events Lead](https://feeny.ai/job/founding-community-and-events-lead-jack-jill-london-15s5c51mqadb) — London, United Kingdom - [Founding Community and Events Lead](https://feeny.ai/job/founding-community-and-events-lead-jack-jill-san-francisco-akt8z88w7scc) — San Francisco, CA - [GTM Engineer](https://feeny.ai/job/gtm-engineer-jack-jill-london-ry95evyjye2j) — London, United Kingdom - [VP B2B Marketing (£250k-£350k+)](https://feeny.ai/job/vp-b2b-marketing-250k-350k-jack-jill-london-bmjfdbcqbn51) — London, United Kingdom - [Senior Account Executive](https://feeny.ai/job/senior-account-executive-jack-jill-london-acdepfj2cs7r) — London, United Kingdom - [Founding GTM Operator SF - (Founding AE)](https://feeny.ai/job/founding-gtm-operator-sf-founding-ae-jack-jill-san-francisco-qj0n5s59ydjm) — San Francisco, CA - [Founding GTM Operator (£150k+)](https://feeny.ai/job/founding-gtm-operator-150k-jack-jill-london-343vwrdfs1jx) — London, United Kingdom - [Founding Designer (£180k+)](https://feeny.ai/job/founding-designer-180k-jack-jill-london-1nfgn1bapxej) — London, United Kingdom - [Founding Engineer (£360k+ )](https://feeny.ai/job/founding-engineer-360k-jack-jill-london-0239zxfxry02) — London, United Kingdom