As the founding Account Executive, you will own the end-to-end sales cycle for an AI teammate transforming property operations. Moving beyond manual processes, you will convert high inbound demand into long-term partnerships with major European operators. This is a high-impact role shaping the GTM motion for a fast-scaling PropTech leader.
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Account Executive at AskVinny
Property operations is a multi-billion-pound industry still stuck in spreadsheets. This Antler-backed startup is changing that with an AI teammate that automates everything from leasing to maintenance for over 200,000 properties. They are looking for their first Account Executive to take over a proven sales motion from the CEO and help scale their managed portfolio by 14x in 2026. If you have 3+ years of B2B SaaS closing experience and want founding equity in a tier-one VC-backed company led by ex-Deel and Goodlord founders, this is the career-defining role you've been looking for.
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Location
Remote (United Kingdom)
Compensation
£50k-£70k + Equity
Company
Vinny
Role overview
Prop Tech20-50 employees
VINNY TECHNOLOGY LIMITED (trading as AskVinny) is a UK-based PropTech company specialising in AI-powered property management software. Its core platform, Vinny, is designed to automate and optimise property operations for owners and operators across sectors including build-to-rent, student accommodation (PBSA), multifamily housing, co-living, single-family rental, and letting agencies. The system integrates seamlessly with existing workflows, automating tasks such as leasing, onboarding, communications, maintenance, compliance, and renewals. Vinny helps property teams provide great resident/customer experiences while improving efficiency and margins, with features including automated inbox management, leasing, renewal, arrears recovery, and portfolio insights. The founding team emphasises rapid product iteration, deep customer engagement, and a growth strategy built on data-driven outbound sales.
What you will do
- Lead consultative sales cycles from qualified SDR handoff to close, navigating complex 3-6 month deals with C-suite and operations directors.
- Conduct high-quality, tailored product demos that articulate the value of AI automation across BTR, student housing, and co-living sectors.
- Partner directly with the CEO to refine pricing strategy, messaging, and the repeatable sales playbook as the company prepares for rapid expansion.
Who this is a fit for
- At least 3+ years of experience closing mid-market B2B SaaS deals, ideally within PropTech, real estate, or complex operational software environments.
- Proven track record of running sophisticated discovery and live demos for both technical and non-technical stakeholders in a fast-paced startup.
- Exceptional communication skills with a remote-first mindset and the ability to bring structure to evolving sales processes and pipeline management.
Why this role is remarkable
- Rare opportunity to join as the first sales hire alongside founders from Goodlord, Deel, and Trustpilot, with clear paths to leadership as the team scales.
- Massive market traction with a product on track to grow managed units by 14x in 2026, backed by tier-one European VCs and Antler.
- High-trust, remote-first culture that prioritizes actual revenue outcomes over activity metrics, featuring quarterly offsites and significant founding equity.
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.
I recruit from Jack’s network and make the intro when I spot a great match.And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
Meet Jack
What happens next?
Jack’s an AI agent for job searching and career coaching. He works for you.
Jill is the AI recruiter working for the company. She recruits from Jack’s network.
If your profile’s a match and Vinny wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.