At a Glance
- Tasks: Drive customer acquisition and expansion in the SF market through innovative sales strategies.
- Company: Join a pioneering AI startup transforming the recruitment landscape.
- Benefits: Competitive salary package, flexible cash/equity options, and a dynamic work environment.
- Other info: Exciting opportunity to build and define sales processes in a fast-paced startup.
- Why this job: Be at the forefront of AI innovation and shape the future of work.
- Qualifications: Proven B2B SaaS sales experience with a track record of exceeding quotas.
The predicted salary is between 72000 - 88000 £ per year.
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. 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.
The Role
Two-thirds of our team are ex-founders. 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. 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: $295k+ total package, flexible on cash/equity split. Location: San Francisco, 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.
Required skills: Artificial Intelligence, Networking, Relationship Building, Outbound Sales. Required languages: English.
Founding GTM Operator SF - (Founding AE) employer: Jack & Jill
At Jack & Jill, we pride ourselves on being an exceptional employer that fosters a dynamic and innovative work culture. Our team enjoys a range of benefits including flexible working arrangements, professional development opportunities, and a collaborative environment that encourages creativity and growth. Located in a vibrant area, we offer unique advantages such as access to cutting-edge technology and the chance to work with industry leaders in AI-driven marketing strategies.
StudySmarter Expert Advice🤫
We think this is how you could land Founding GTM Operator SF - (Founding AE)
✨Leverage Your Network
In sales and business development, who you know can often be as important as what you know. Get involved with local networking events or industry meetups to connect with key players. Don't be shy—share your passion for the field and let folks know you're on the lookout for opportunities!
✨Show Your Skills Through Real-World Results
When targeting a full-time role like Founding GTM Operator SF - (Founding AE) at Jack & Jill, presenting tangible results from your previous sales experience can set you apart. Bring along case studies or examples of how you've closed deals or expanded accounts, and don't forget to showcase your problem-solving prowess. It’s all about quantifying your success!
✨Engage with Sales Communities
Dive deep into online sales communities, like Sales Hacker or LinkedIn groups dedicated to sales professionals. Engaging in discussions and sharing insights can boost your visibility and might just put you on the radar of hiring managers looking for fresh talent in business development.
✨Direct Applications Matter
While we all know the online application route, consider sending direct applications to companies you admire, including Jack & Jill. Tailor your message to explain why you’re drawn to them and how you can contribute as a Founding GTM Operator SF - (Founding AE). Sometimes, a personal touch can grab attention faster than a generic application!
We think you need these skills to ace Founding GTM Operator SF - (Founding AE)
Some tips for your application 🫡
Show Off Those Sales Skills:In your CV and cover letter, highlight any previous sales or business development experience you have. Use numbers and examples to showcase your achievements – did you exceed sales targets or bring in new clients? Make those accomplishments shine!
Tailor Your Message for Jack & Jill:When writing your cover letter, make sure to tailor your message specifically for Jack & Jill. Show that you know the company’s mission and how your skills align with their goals in the sales landscape. This personalised touch will grab their attention!
Keep It Professional Yet Engaging:Sales is all about relationships, so while you want to maintain professionalism in your application, don’t be afraid to let your personality shine through. Engage the reader and demonstrate your enthusiastic approach to sales and business development!
Proof of Performance:Include any relevant certifications or training you’ve undertaken in sales or negotiation tactics. If you’ve attended workshops or courses, list these to showcase your commitment to professional development. This extra touch can set you apart from the competition!
How to prepare for a job interview at Jack & Jill
✨Know Your Sales Methodologies
Brush up on popular sales methodologies like SPIN Selling or Challenger Sales. Being able to discuss these techniques and how you've applied them will show Jack & Jill that you understand the role and can hit the ground running in the sales game.
✨Demonstrate Your Deal-Making Skills
Prepare to share stories from your past experiences where you closed deals, overcame objections, or started new client relationships. We want to show Jack & Jill that you’re not just about numbers but also about building lasting connections in business development.
✨Prepare for Role-Play Scenarios
In a full-time sales interview, don’t be surprised if they throw in a role-play exercise to test your pitching skills. Practising how you would pitch a product or handle an objection will help us shine in this simulation—think of it like a dress rehearsal for your future sales calls!
✨Align Your Goals with the Company’s Vision
Take a moment to reflect on how your career ambitions align with Jack & Jill’s objectives. When we articulate how our personal growth ties in with the company’s goals, it shows commitment and a genuine interest in contributing to their success.
