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.

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• 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.

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• 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

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• 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