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

1. 30 min screening call with Talent

2. 45 min interview with Director of Sales

3. 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