Founding Operator

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 10 months old, have released two agentic products (Jack and Jill), have built a brilliant team of Europe’s best engineers, operators and ex founders, are run rating over £1m revenue and have raised $20M, led by tier-1 VC Creandum. 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 hiring a Founding Operator to join our Jill Delivery team. You won't be in a box. You’ll work directly with our Jill Delivery Lead on our highest-leverage customer challenges, turning ideas into reality fast and making sure what we build actually works in the real world. The initial mission is driving the Jill customer experience post-sale: a role that spans account management, customer success, expansion, product feedback, and the operational systems that underpin all of it. You’ll be responsible for taking customers from their first spark of value to a long-term, expanding relationship with Jill. As the company evolves, so will your focus. This is a 0→1 role. You’ll start by doing things manually (jumping on calls, reviewing roles, nudging workflows) to understand where things break and where the value is. Then you’ll build the playbooks, tooling, and operating rhythms that make great delivery repeatable.

What you’ll actually do:

• Take customers from interested to successful. You’ll pick up from the sales team once a customer has seen their first spark of value and take it from there. You’ll build the relationship, drive deep adoption, and get them to hires as fast as possible.
• 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 as much a commercial role as it is a delivery role. When a customer starts to see value from Jill, your job is to make sure they immediately put another role in. You’ll identify expansion opportunities across your book of business, build the relationships that make saying yes easy, and be accountable for growing revenue from existing customers, not just protecting it.
• Manage relationships. Be the trusted point of contact for a portfolio of customers. Spot risk early, handle escalations calmly, and build the kind of partnerships where customers come to you before they even think about churning.
• Feed the product. You’ll be closer to customer reality than almost anyone. Feed sharp, structured insight back to product and engineering so we keep building the right things.
• Build the machine. Document what works, kill what doesn’t, and turn manual effort into repeatable process. Build dashboards, workflows, and feedback loops that make the team smarter every week.

You’ll be a great fit if:

• 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’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. This gives you genuine empathy with our customers.
• You have account management or CS 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 love turning chaos into process. You build clear trackers, structured workflows, and lightweight tooling that make the team faster. You use AI properly, not just as a novelty, but as a genuine force multiplier.
• You have some technical chops. You don’t need to be an engineer, but if you can hack together a script, build an automation, or hold your own in a technical conversation, you’ll be significantly more effective in this role. A background that touches code in some way is a real plus.
• You’re high agency. You don’t wait to be told what to do. You identify the highest-leverage problem and move on it.

The profile

We’re open to exceptional people from a range of backgrounds, but you likely fit one of these:

• The Hiring-Aware Operator: You’ve been part of hiring processes, whether as a hiring manager, a founder building out a team, or someone embedded in a scaling org. You understand the frustration and the stakes, and that perspective shapes how you show up for customers.
• The CS/AM Builder: You were an early customer success or account management hire at a fast-growth B2B startup. You’ve built from scratch, managed a growing book of business, and know what it takes to make customers genuinely successful.
• The Ex-Founder: You’ve built something before, worn every hat, and are ready to go 0→1 again in a high-ownership role at a rocketship.

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 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 two of the best 0 -> 10 GTM leaders in the world.

And there’s also the perks…

• Total Compensation for this role of £100-180k+ (we let you choose your cash : equity split)
• Private health insurance with Bupa
• 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 B2B Delivery Lead. 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.