Head of Sales

🚀 Play a Leading Role in Transforming an Industry with AI Technology!

We’ve spent the past few years building one of the UK’s most exciting Legaltech companies, backed by top-tier investors, trusted by global law firms, and recognised as Commercial Team of the Year in 2024. Now, we’re bringing that success to the US.

We’ve just begun building our presence stateside, with a small but mighty team on the ground in New York, and we’re looking for a Head of Sales to help us scale that early momentum into a world-class commercial engine.

Reporting directly to the CRO, you’ll ramp a team of Account Executives by the end of 2025 and shape the systems, culture, and performance needed to scale into Series B and beyond.

• Build and lead a high-performing team of AEs, coaching and mentoring for consistent quota attainment and continuous growth.
• Drive performance and process discipline using MEDDIC/MEDPIC methodology, HubSpot CRM, Apollo, SalesNav, and Jiminny.
• Implement and iterate repeatable sales processes for discovery, pilot structuring, and complex deal cycles.
• Own key metrics: pipeline coverage, forecast accuracy, deal velocity, and team productivity.
• Coach, mentor, and guide team members while remaining hands-on in key deals, negotiations, and late-stage execution.
• Be the operational nerve centre of US GTM, collaborating across Sales, Product, CS, and Marketing.
• Foster a growth-oriented, collaborative team culture that values trust, accountability, and customer-centricity.
• Influence national expansion strategy as we explore new regional offices and sectors in 2026.

• 6 AEs fully ramped and consistently closing new business.
• Healthy pipeline and revenue predictability aligned to Series B growth goals.
• Sales process is embedded, scalable, and owned by the team.
• The US GTM team is viewed as a collaborative, accountable, and culture-aligned unit.
• You're a key contributor to our Series C readiness.

This is more than your typical Head of Sales role, it’s a chance to redefine an entire industry using Generative AI and machine learning. Property is the world’s largest asset class, and we’re revolutionizing how deals are evaluated and transacted. You'll help transform how legal and professional services teams operate, while shaping one of the most important new markets in our business.

• You have 5–8 years of B2B SaaS sales experience, including individual contributor success and minimum of 1–2 years of sales leadership.
• You’ve led teams selling complex SaaS into professional services, legal, or financial sectors, navigating multi-stakeholder deals.
• You’re fluent in value-based selling and deal qualification frameworks (MEDDIC/MEDPIC).
• You’ve operated in early-stage, scaling SaaS environments, comfortable building amid ambiguity.
• You know your way around a modern sales stack (HubSpot, Apollo, SalesNav, Jiminny).
• You’re a hands-on leader who’s driven, dependable, and team-focused.
• You care deeply about coaching, mentoring, and building a team that performs and grows.

Bonus if you have:

• Experience scaling a team through Series B–C.
• Background in legaltech, proptech, fintech, or similar complex SaaS categories.
• Regional sales expansion experience across the US.

Compensation: Base salary of $150,000-180.000 depending on experience, with an OTE of $300,000-360,000. We share salary ranges upfront to build trust, reduce bias, and support an inclusive process, even as we continue developing our internal pay structures.

Comprehensive health benefits: Your well-being is important to us. We provide competitive medical, dental, and vision coverage to help you stay healthy and supported.

Flexible Work: We believe in flexibility, but we’re also big on in-person collaboration. This role is based in our Manhattan office three days a week (Monday, Wednesday, and Thursday).

Preparing for your future: We offer a healthy 401(k) match.

Ownership: We give you real ownership in the company through stock options, so you share in our success.

Rest and Recharge: You’ll receive 20 days of paid vacation, in addition to 11 public holidays. We encourage real breaks so you can show up as your best self.

Equipment & Development: We invest in your growth with top-quality gear, a $1,200 annual development budget, and ongoing training to help you build skills and confidence from day one.

Commuter Benefits: We support your commute. Whether you’re taking the bus, train, or subway - by helping you use pre-tax dollars to offset the cost.