Head of Enterprise Sales

CUBE are a global RegTech business defining and implementing the gold standard of regulatory intelligence for the financial services industry. We deliver our services through intuitive SaaS solutions, powered by AI, to simplify the complex and everchanging world of compliance for our clients. 

Why us?

🌍 CUBE is a globally recognized brand at the forefront of Regulatory Technology. Our industry-leading SaaS solutions are trusted by the world’s top financial institutions globally.

🚀 In 2024, we achieved over 50% growth, both organically and through two strategic acquisitions. We’re a fast-paced, high-performing team that thrives on pushing boundaries—continuously evolving our products, services, and operations. At CUBE, we don’t just keep up we stay ahead.

🌱 We believe our future is built by bold, ambitious individuals who are driven to make a real difference. Our “make it happen” culture empowers you to take ownership of your career and accelerate your personal and professional development from day one.

🌐 With over 700 CUBERs across 19 countries spanning EMEA, the Americas, and APAC, we operate as one team with a shared mission to transform regulatory compliance. Diversity, collaboration, and purpose are the heartbeat of our success.

💡 We were among the first to harness the power of AI in regulatory intelligence, and we continue to lead with our cutting-edge technology. At CUBE, You will work alongside some of the brightest minds in AI research and engineering in developing impactful solutions that are reshaping the world of regulatory compliance.

Overview

The Head of Enterprise Sales, North America will own all commercial outcomes across the region, with a mandate split equally between expanding our existing enterprise footprint and aggressively acquiring new logos. This is a senior team leadership role, sitting on the global sales leadership team and reporting directly to the Chief Sales Officer.

CUBE is the market leader in regulatory intelligence, already trusted by a significant number of the world's largest financial institutions. North America is our number one market — and there is still substantial headroom to grow. Major US and Canadian banks, asset managers, and insurers continue to face mounting regulatory pressure, and our consolidation story (replacing multiple legacy vendors with a single intelligent platform) resonates strongly at C-suite level. Beyond financial services, we are expanding into large enterprise technology accounts, and this leader will play a central role in building that presence alongside our core FS base.

Key Responsibilities

New Logo Acquisition

• Drive net new enterprise logo acquisition with a primary focus on major US and Canadian financial institutions — Tier 1 and Tier 2 banks, asset managers, insurance companies, and specialty finance firms — and a secondary focus on large enterprise technology companies

• Build and execute a structured outbound motion — this team is transitioning from inbound-led to a disciplined outbound engine, and this leader will be central to making that shift

• Partner with the BDR function (sitting within Marketing) to drive top-of-funnel pipeline at scale

• Lead complex, multi-stakeholder sales cycles from initial engagement through to signed contract

• Develop and deepen relationships at CRO, CCO, and procurement level across target accounts

• Target minimum £200K ACV per new logo with clear path to seven-figure expansion

Enterprise Expansion

• Own NRR targets of 130-140% across the regional book of business

• Partner with Customer Success to identify and execute upsell and cross-sell opportunities across CUBE's full product suite

• Drive expansion of existing accounts into new business lines, jurisdictions, and user groups

• Lead commercial negotiations on renewal and expansion agreements at enterprise level

Team Leadership

• Recruit, develop, and retain a high-performing sales team across the full North America region

• Drive a culture of outbound excellence — building the habits, cadences, and accountability structures that shift the team from reactive to proactive

• Elevate the team's ability to engage and influence at senior stakeholder level, including CRO and CCO

• Build structured territory and account plans covering both the US and Canada

• Establish repeatable sales methodology and rigorous pipeline discipline

• Maintain clean Salesforce hygiene and accurate forecasting for weekly and quarterly reporting

• Collaborate closely with Solutions Engineering, Customer Success, and Product to win complex deals

Market Development

• Develop deep knowledge of the US and Canadian financial services landscape across banking, asset management, and insurance

• Build CUBE's profile across North America through events, roundtables, and strategic partnerships

• Partner with Marketing on demand generation and thought leadership initiatives

• Contribute regional intelligence to inform product roadmap and GTM strategy

Required Qualifications

• 10+ years enterprise software sales experience, with at least 3 years in a regional leadership role

• Proven track record of consistent quota attainment at £5M+ annual targets

• Demonstrated success selling into major US and Canadian financial institutions at senior stakeholder level — C-suite engagement (CRO, CCO, CEO) is essential

• Experience building and leading outbound sales motions, including partnership with BDR teams and structured prospecting programmes

• Experience managing complex, multi-threaded sales cycles of 6-18 months

• Track record of both new logo acquisition and account expansion in the same role

• Exceptional executive presence and C-suite communication skills

• Based in or willing to relocate to New York or Boston; willingness to travel regionally 30-40%

Desired Qualifications

• Experience selling into large enterprise technology companies (hyperscalers, global tech firms) in addition to financial services

• Strong understanding of regulatory compliance, risk management, or financial services technology

• Existing senior relationships across Tier 1 US and Canadian financial institutions (bulge bracket banks, major asset managers, large insurers)

• Experience selling into Chief Compliance Officer, Chief Risk Officer, or Chief Legal Officer organisations

• Familiarity with US and Canadian regulatory frameworks (Dodd-Frank, SEC, FINRA, OSFI, FHFA)

• RegTech, FinTech, or compliance software background

• Experience with acquisition-integrated product portfolios and migration sales motions

• Track record of building teams in a high-growth, private equity-backed environment

Interested?

If you are passionate about leveraging technology to transform regulatory compliance and meet the qualifications outlined above, we invite you to apply. Please submit your resume detailing your relevant experience and interest in CUBE.​

CUBE is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.