Head of US Distribution & Sales

Descartes Underwriting•Chicago, TX

1d•Hybrid

About The Position

Descartes is hiring a Head of US Distribution and Sales to lead and deliver the US business plan through the development of a world-class sales organization. This role involves building a focused commercial engine that scales new business across retail brokers and corporate/public-sector clients, while deepening relationships with existing partners. The ideal candidate will have an entrepreneurial, builder's mindset, ready to structure, coach, and motivate a high-performing business development team of 10+ FTEs. This role requires the discipline to implement rigorous sales processes and the energy to keep a distributed team engaged, accountable, and moving toward its goals. The US Business Development team is spread across 7 states, requiring comfort in leading, coaching, and holding a geographically distributed team accountable, largely through structured remote cadences (pipeline reviews, deal coaching, 1:1s). Regular travel (~1 week per month) is expected to be in the field with BDs, brokers, and clients.

Requirements

Proven track record as a sales leader of a team of at least 10 FTEs — must have demonstrated experience coaching and developing top performers with a focus on results.
Direct experience managing a geographically distributed/remote sales team, with the discipline to run effective remote pipeline reviews and coaching without relying on daily in-person oversight.
Willingness to learn and understand the traditional and specialty insurance landscape and the parametric insurance value proposition.
Experience with long, technical, multi-stakeholder B2B sales cycles.
Demonstrated ability to enforce sales process discipline, CRM hygiene, and comp/incentive structures with rigor — someone who operationalizes an existing framework.
Strong personal ability to engage and influence the outcomes of complex, high-value deals through individual interaction and action, including intervention as needed.
Comfort operating with firmness and judgment in a structured, remote-first environment, building, executing and scaling a sales approach.

Nice To Haves

Experience as a sales leader in the corporate insurance or reinsurance industry.
Existing network among US corporate insurance brokers, reinsurers, MGAs, or corporate risk managers.
Experience working in a scaling company.
Experience working in a regional business unit.

Responsibilities

Lead and build a high-performance, entrepreneurial sales culture: set clear expectations, keep a distributed team aligned and energized, hold team accountable to performance standards, and celebrate wins in a way that fits a broker-driven sales environment.
Manage a geographically distributed Business Development team: run structured remote pipeline reviews, forecast calls, and 1:1 coaching, and travel regularly to spend real time in the field with BDs, brokers, and clients.
Structure and develop a team of high performing business developers: hire, onboard, and coach BDs; ensure succession planning and knowledge sharing within the team.
Contribute to the development of the Sales Plan in collaboration with the Head of the Americas and Executive team.
Drive Business Development Team performance to achieve the Sales Plan through proactive involvement and coaching; identify and clear blockers; intervene when and where necessary and be a point of escalation to facilitate course correction externally and internally in collaboration with stakeholders.
Join meetings involving key partners and clients: support the BD and the business at whatever stage of the sales cycle is required including prospecting, negotiation and closing.
Feed and act on market intelligence to leadership.
Implement and iterate on the BD Sales Playbook; ensure the execution of repeatable sales process from broker outreach to closing deals.
Own CRM and pipeline discipline: drive the forecasting cadence, pipeline hygiene standards, and reporting rhythm expected by global leadership.
Apply and refine incentive structures in collaboration with Head of Americas and executive team: manage compensation plans and KPIs for Business Developers that reward both activity and pipeline quality, adjusting as needed for long, broker-mediated sales cycles.
Execute the US go-to-market approach: drive prioritized target segments and perils/products, in coordination with global leadership.
Collaborate closely with underwriting, translating market needs and broker/client feedback into product and coverage improvements that expand the addressable market.
Collaborate with commercial counterparts in other Hubs to maximize business development opportunities and share best practices.