Founding Operator
Jack & Jill
Founding Operator
Jack & Jill
Conversational AI hiring marketplace matching candidates
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 just raised $40M Series A, led by Air Street Capital with participation from Creandum and Madrona. Read more here https://www.jackandjill.ai/blog/series-a
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.
We're hiring a Founding Operator to join our Jill Delivery team, working alongside Ed Steele and Ed Kim. 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'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.
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.
🖥️ 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.
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
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.
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 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
Conversational AI hiring marketplace matching candidates
Jack & Jill is a London-based hiring marketplace that uses conversational AI to automate parts of the recruiting process on both sides of the deal. Jack acts as a voice-based coach for jobseekers, scanning millions of open roles and helping candidates present themselves, while Jill works for employers to refine role success criteria and source candidates from Jack’s network rather than from public applicant pools. When Jack and Jill agree on a match, they introduce the candidate and employer directly, enabling easier conversations and faster hiring. The company differentiates itself by leveraging a large professional network (about 380,000 people) and a targeted sourcing approach instead of traditional open pools, with traction in the US market and leadership from founders with strong hiring and tech backgrounds. Its goal is to scale expansion in the US and grow its network to speed up and improve hiring outcomes for both sides of the market.
Explore more opportunities at Jack & Jill