Borderless
Enterprise Account Executive
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About Us
Borderless is simplifying the complexity of global immigration, starting with the UK.
Immigration is one of the most important — and most broken — systems in the global economy. It’s shaped human history, yet businesses and individuals hit friction at every turn, and government policy lurching with the political cycle.
Our vision is simple: a world where borders are no longer barriers, empowering the ambitious, wherever they are. Backed by Entrepreneur First and Backed.VC, we’re already supporting 600+ businesses, 15,000+ workers and scaling fast into new sectors and markets.
Around 25% of our workforce is sponsored, and we proudly offer visa sponsorship as part of our hiring process.
Role: Enterprise Account Executive
As a founding Enterprise Account Executive, you will be a critical architect of our move into mid-market and enterprise segments, owning the full 360 sales cycle for high-value commercial opportunities. You will play a pivotal role in defining the "rule book" for complex sales at Borderless, helping us scale our reach across the care, tech, and construction sectors.
What You'll Be Doing
- Build a robust, self-generated pipeline of opportunities with a typical deal size of £50k–£100k+ by identifying and prospecting high-potential accounts, while partnering closely with the Commercial Growth team to refine target account lists and optimise your territory strategy.
- Lead structured, value-based discovery sessions to uncover deep business pain, compliance risks, and commercial drivers within larger organisations.
- Manage multi-stakeholder sales cycles lasting 6+ months, expertly navigating conversations with founders, finance, HR, and senior leadership.
- Execute tailored product demonstrations that connect Borderless solutions directly to a prospect’s specific operational challenges and desired outcomes.
- Orchestrate the entire commercial process, from conducting formal proposal meetings to managing complex contract negotiations and final signatures.
- Maintain meticulous CRM hygiene within HubSpot, ensuring accurate forecasting and clear stage discipline across all active deals.
- Collaborate cross-functionally with onboarding and customer success teams to ensure a seamless and high-quality transition for new enterprise partners.
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You Should Apply If:
- Proven Sales Track Record: 3–5 years of experience in a full-cycle Mid-Market or Enterprise AE role, with evidence of consistently achieving targets in deals exceeding £50k annual value.
- Strategic Prospecting: The ability to move beyond inbound demand by researching, mapping, and engaging senior stakeholders through structured outbound activity.
- Commercial Acumen: Strong skills in value-based selling, qualification, and negotiation, with the ability to protect margins and build compelling business cases.
- Process Discipline: A commitment to operating within a structured sales system, maintaining high standards for HubSpot hygiene and pipeline management.
- Communication & Presence: Exceptional written and verbal communication skills, with the confidence to challenge senior stakeholders professionally and build long-term trust.
- Growth Mindset: A team-first, coachable attitude with the urgency to solve problems quickly and a desire to help define the sales "rule book" in a high-growth environment.
Success in the Role
- After 30 Days: You will have mastered the Borderless value proposition, completed sales methodology training, and built your initial target account list. You’ll be shadowing calls and demonstrating a deep understanding of the compliance challenges within the care sector.
- After 60 Days: You will be actively managing your own pipeline, running structured discovery calls, and progressing self-generated opportunities through the demo and proposal stages with high levels of qualification.
- After 90 Days: You will be operating with full independence, owning a healthy pipeline of enterprise deals and showing clear evidence of repeatable sales behaviours that contribute to the team’s commercial impact.
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Requirements
The Enterprise AE must have:
- Experience in a full cycle or 360 sales role.
- Experience creating their own pipeline.
- Evidence of consistent target achievement.
- Ability to sell to senior stakeholders.
- Strong discovery and qualification skills.
- Strong commercial awareness.
- Experience managing complex or higher value sales cycles.
- Confidence running proposal and negotiation meetings.
- Strong written and verbal communication.
- High standards of CRM hygiene.
- Ability to work with pace and accountability.
- Coachability and openness to feedback.
- A team-first mindset.
Nice to Have:
- Experience selling B2B SaaS.
- Experience selling into care, healthcare, HR, compliance, or regulated sectors.
- Experience selling to owner-led, founder-led, or operationally complex businesses.
- Experience with HubSpot.
- Experience selling both technology and service-led solutions.
- Experience working in a high-growth environment.
- Experience managing deals with multiple stakeholders and approval steps.
Interview Process
- 30 min screening call with Talent
- 45 min interview with Director of Sales
- In-person final interview with the CEO and hiring manager
Benefits
- 3 days in office, 2 days remote
- Monthly company in-office lunches
- Monthly company team events
- Annual offsite (our last one was in Palma!)
- Comprehensive private medical insurance
Holidays & Remote Work
- 25 days holiday each year + 3 days between 25th December and 31st January, plus bank holidays
- 1-week work-from-anywhere policy
Growth & Development
- £500 annual Learning & Development budget
- 6-month performance reviews and promotion opportunities
Equipment & Other Perks
- Laptop and peripherals — whatever you need to work effectively
- Cycle to Work scheme
- Employer pension contributions via Smart Pension
- Access to Spill (mental health support)
- Gym in Shoreditch Exchange
- Onsite barista
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