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Head of Sales - Founding GTM Lead!
London · Old Street · Onsite (5 days/week) · Skippr AI
Direct applicants only (no agencies)
Hey, we're Skippr AI ✨
The Live AI Employee, serving every user. We build real-time agents that see, talk, and operate software — they onboard, activate, and unblock your users, on their own. We're a small, 100% AI-native team in Old Street, London, backed by Bessemer Venture Partners, Moonfire, and angels from Google, Twilio, and Meta. We don't just build agents — we use AI to run our own GTM every single day.
If you've done first sales before and want to do it again with a passionate team behind you, we should talk.
What you'll do
- Own the revenue: Deals end-to-end — first contact to signed contract. You're the initiator and the closer. We don't work like traditional companies with role players; we believe in Swiss-army-knife people, backed by agents we deploy weekly to cover wherever we're weak.
- Open doors at the top: AI-powered outbound automation is already running. We're hiring for what machines can't do: activating your industry relationships and using your network to build more, creating C-level conversations, and turning them into deals.
- Tell the story: You'll be the voice of Skippr in the market — a storyteller by heart who can make "the Live AI Employee" land with the right ears.
- Work directly with the founder: Help shape the sales playbook as we learn from every deal. Your input changes what we build.
- Grow into a wider role: We don't have a CRO or VP Sales — this seat is the foundation of our commercial org. Prove it with revenue and the scope might grow with you.
Reasons to use Rodeo
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No noise. No "maybe this fits." Just roles with a clear explanation of why they're right — and where to focus when applying.
This role is for you if
- You've done 0→1 before: sold an AI product or B2B SaaS from the early stage and personally brought the first sales — logos you sourced, ran, and closed yourself.
- You're hands-on: you prospect, pitch, negotiate, and close.
- You bring relationships, not just process — a network you can activate and a track record of building C-level trust fast.
- You've sold into customer-facing teams (CS, enablement, support) and their executives — a real advantage. But our product goes beyond any one function, so we're hiring on track record, not vertical.
- You've sold globally — Europe and US experience, not a local focus (although we do sell in the UK!)
- You have startup DNA: comfortable with ambiguity and imperfect information.
Get help with your application
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This role is not for you if
- You want remote or hybrid work. We believe early-stage startups win by moving fast in the same room — five days a week in our Old Street office, with travel when needed. We learn more together.
- You look for certainty and repeatability. If you want insurance-style deals that repeat for life, a stable brand, and a polished playbook, this isn't the place. Here, you help write the playbook — and love the 0→1 of it.
- You aren't obsessed, like we are, with what live AI agents can and will do to the modern workforce — living every new release in the market and trying every tool hands-on.
What we offer
- Aggressive OTE plus meaningful equity (EMI options): Everyone here has skin in the game.
- The chance to define an entirely new market for AI agents — and be the person who sold it first.
- Comprehensive benefits: Pension, private health insurance, and 25 days holiday plus bank holidays.
- A team that's genuinely excited: Obsessive about the problem, in love with what we're building, sharp but supportive culture.
“It took my CV and asked me questions relevant to understanding what kind of jobs to suggest for me. Suggestions were almost perfect. Jobs were exactly what I’ve been looking for.”
Jessica, London
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