Enterprise Account Executive

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.

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.

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