Senior Director, (Re)Insurance Sales

Hyperproof; New York (NY); Hybrid; USD 180,000 - 260,000; Full time

Job summary

CyberCube is seeking a first-line sales leader to own the (re)insurance revenue segment across UK/Europe and North America. You will lead the team, own the numbers, and be credible in front of CROs and Chief Underwriting Officers.

You will hire, coach, and manage performance, drive pipeline discipline, and oversee renewal/expansion. Travel to key markets; build coverage with senior insurance buyers to accelerate growth.

Qualifications

• Proven first-line sales leadership with quota-carrying teams.
• Experience selling complex software/data to large enterprises.
• Enterprise deal cycles with six to twelve month cycles.
• Executive credibility with CRO/Chief Underwriting Officer.

Responsibilities

• Lead the (re)insurance sales and account management team across UK/Europe and North America.
• Hire, coach, and manage performance; retain and stretch top performers.
• Manage pipeline coverage, conversion, activity, and cycle time with CRM discipline.
• Lead renewal and expansion motions across assigned territories.
• Shorten time from qualified opportunity to signature; hold the room with senior buyers.

Skills

Sales leadership

Enterprise software

Six figure deals

Multi-stakeholder

Forecasting discipline

Executive credibility

Tools

CRM

Job description

About CyberCube:

CyberCube delivers the world's leading analytics to quantify cyber risk, translating one of the most critical risks of today and the future into financial impact for businesses, markets, and society.

• AI at our foundation, cyber risk at our core. We don't just use AI, we shape it.

• Built on AI from day one. Artificial intelligence has been part of our strategy since the beginning, blended with deep cybersecurity and insurance expertise and backed by rigorous testing.

• Trusted by more than 100 clients, including 75% of the top 40 European and US cyber insurance carriers and 70% of the top ten reinsurance brokers.

• Backed for global growth. In 2025 Spectrum Equity joined some of CyberCube’s financial partners as a new cornerstone investor, accelerating our global growth and fueling innovation across our end-to-end cyber risk analytics for the insurance industry.

• A truly global team across San Francisco, New York, London, and Tallinn.

• A culture of collaboration, openness, intellectual rigor, and ownership for excellence.

• People at the forefront. We encourage CyberCubers to challenge themselves, push boundaries, and do the best work of their careers.

The Role

CyberCube is hiring a first-line sales leader to own our largest revenue segment: the (re)insurance sales and account management team across UK/Europe and North America.

Context

CyberCube is the market-leading cyber risk analytics platform for the insurance industry, serving large global carriers, reinsurers and brokers. The (re)insurance segment is our largest and most established revenue base, spanning new business and renewals across the UK/Europe and North America.

The team, the territory, and the pipeline are in place. This is a senior leadership role, not a build from scratch role. The postholder leads the team, owns the number, and is personally credible in front of a CRO or Chief Underwriting Officer.

What You Will Do

• Lead the (re)insurance sales and account management team across UK/Europe and North America and deliver the segment number, with a forecast we can rely on quarter to quarter.

• Hire, coach, and performance manage the team. Retain and stretch top performers.

• Run the team off numbers. Pipeline coverage, conversion, activity, cycle time. Hold a forecast, evidence it, and be held to it, with weekly inspection and CRM discipline.

• Lead the renewal and expansion motion.

• Shorten the time from qualified opportunity to signature.

• Named account coverage and territory design fit for purpose across UK/Europe and North America.

• Coach in the deal rather than from the sidelines. In the room with the team on the meetings that matter.

• Hold the room with senior insurance buyers (CUO, CRO, Chief Actuary, Head of Cyber, Head of Exposure Management) and earn a second meeting on their agenda, not ours.

• Set the tempo for the team. Travel and be visibly in market rather than managing from a desk.

What We Look For

• Proven first-line sales leadership. Has managed a team of quota-carrying sellers and ideally account managers, and hit team targets over multiple cycles.

• Has sold complex software, data or analytics into large enterprise buyers, and has led a team doing the same. Long cycles, multiple stakeholders, technical evaluation, six- and seven-figure ACVs.

• Enterprise deal experience. Multi-stakeholder, procurement and legal heavy, six to twelve month cycles, subscription or licence commercial models.

• Metrics-oriented. Knows their pipeline coverage, conversion and cycle times without looking them up, and coaches the team against those measures.

• Executive credible. Can walk into a CRO or Chief Underwriting Officer and be taken seriously on the first meeting. Articulate on the commercial argument, unfazed by seniority, trusted to represent CyberCube without supervision.

• Operates with urgency, treats a slow decision as a cost, and lifts the energy of the team.

• A demanding, high-accountability leader who sets a high bar. Direct with feedback, quick to address underperformance, and respected for it.

• Commercially creative on structure and pricing, disciplined on process and reporting.

• Low ego, high candour. Comfortable disagreeing with the executive team and being disagreed with.

• Based in London or New York, with regular international client travel.

Strong Plus

• Has sold into the insurance or reinsurance industry. Carriers, reinsurers, brokers, MGAs or the Lloyd's market. A major differentiator, but not a requirement.

• Experience across both new business and renewals/expansion, including usage-based or consumption pricing conversations.

• Exposure to reinsurance and broker channels as well as primary carriers.

• Has scaled a team through a step change in growth expectations.

• Cyber, catastrophe modelling, exposure management or InsurTech adjacency.

• Comfort in a fast-moving, AI-enabled commercial function. Agentic prospecting, automated reporting, no traditional SDR layer.

Not Required

• Deep technical cyber security or catastrophe modelling knowledge. We have that in the business.

• Underwriting or actuarial background.

• Direct competitor experience.

AI Fluency at CyberCube

AI is reshaping how work gets done across every function. We value people who are curious about AI, eager to learn, and thoughtful about applying AI tools to work more effectively. AI fluency is part of how we assess every role in our hiring process.

Equal Opportunity Statement

CyberCube Analytics, Inc. and CyberCube Analytics Europe Limited is an equal opportunity employer. We don’t tolerate discrimination against age, gender, gender identity, gender expression, sexual orientation, race, color, nationality, ethnicity, religion, disability, veteran status, protected genetic information or political affiliation.