Jack & Jill
Enterprise Account Executive (£160k-£200k) at Borderless
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Job Title
Enterprise Account Executive
Salary
£80k-£100k + £160k-£200k OTE
Company Description
Borderless is a seed-stage London startup backed by Entrepreneur First and Backed VC that is automating the complex global immigration system. Founded in 2023, they have already scaled to support over 600 businesses and 15,000 workers, replacing fragmented legal processes with a single, elegant digital sponsorship and compliance platform.
Job Description
As a founding Enterprise Account Executive at Borderless, you will architect the company's move into the mid-market and enterprise segments. You will own the full 360-degree sales cycle for high-value deals (£50k–£100k+), navigating complex multi-stakeholder environments across the healthcare, tech, and construction sectors to solve critical global immigration challenges.
Location
London, UK
Why this role is remarkable
- Join as a founding member of the enterprise sales team, directly defining the strategy and sales playbook for a category-defining company in a high-stakes market.
- Work at the intersection of technology and policy at a seed-stage startup backed by top-tier investors like Entrepreneur First and Backed VC, solving a broken global system.
- High-impact visibility with direct access to the CEO and Sales Director, operating in a mission-driven environment where 25% of the workforce is sponsored by the product they build.
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What You Will Do
- Build and manage a robust self-generated pipeline of high-potential accounts, targeting deal sizes between £50k and £100k+ within regulated sectors like healthcare and construction.
- Lead complex, multi-stakeholder sales cycles lasting 6+ months, navigating value-based discovery sessions with founders, HR directors, and C-suite executives to uncover deep compliance pain.
- Orchestrate the entire commercial process from initial prospecting and tailored product demonstrations to managing contract negotiations and ensuring seamless handovers to customer success teams.
The ideal candidate
- 3–5+ years of experience in a full-cycle Mid-Market or Enterprise AE role with a proven track record of consistently achieving targets on deals exceeding £50k annual value.
- Exceptional strategic prospecting skills, with the ability to map accounts and engage senior stakeholders through structured outbound activity rather than relying solely on inbound demand.
- High commercial acumen and process discipline, including mastery of value-based selling and meticulous CRM hygiene within HubSpot to ensure accurate forecasting and pipeline management.
Who are Jack & Jill?
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.
Get help with your application
Your very own career expert that helps elevate your application to the next level.
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.
How does this work?
- 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 it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.
We never post fake jobs
This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.
Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.
We appreciate this can make them look a bit suspect, but there isn't much we can do about it.
Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.
“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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