Head of Regional Sales (Northeast)

SageSure•Cincinnati, OH

5h•Hybrid

About The Position

SageSure is seeking a strategic leader to own regional performance and execution as the Head of Regional Sales, Northeast. This role is accountable for driving profitable growth, deepening agency engagement, and ensuring consistent execution of SageSure’s go-to-market strategy across New York, Massachusetts, Connecticut, and New Jersey. The Head of Regional Sales will lead and develop a high-performing regional sales team, partner closely with underwriting, product, operations, and marketing, and translate enterprise strategy into measurable regional results. Success requires strong market knowledge, disciplined field execution, data-driven decision-making, and the ability to influence stakeholders.

Requirements

Extensive experience in insurance sales leadership, preferably within property, personal lines, or catastrophe-exposed markets.
Proven success leading regional sales teams and driving measurable growth across complex, competitive territories.
Strong understanding of Northeast insurance markets, agency distribution models, and regulatory considerations.
Demonstrated ability to hold teams accountable to activity, execution standards, and business outcomes.
Data-driven mindset with experience using CRM systems, dashboards, and analytics to manage performance.
Strong executive presence with the ability to influence senior leaders, agency principals, and cross-functional partners.
Excellent communication skills, both written and verbal, with the ability to deliver clear, compelling messages.
Comfort operating in a matrixed organization and partnering across underwriting, product, operations, and marketing.
Bachelor’s degree in business, finance, marketing, or related field (or equivalent experience).

Nice To Haves

Deep relationships with Northeast agency partners or regional broker leadership.
Experience leading sales efforts across multiple states with varying market dynamics.
Familiarity with Salesforce, BI tools, and performance scorecards.
Prior experience working within an MGU, carrier, or specialty insurance platform.

Responsibilities

Own full accountability for regional sales performance, including new business growth, retention, mix of business, and overall territory health across the Northeast.
Lead, coach, and develop a high-performing regional sales team, setting clear expectations tied to activity, outcomes, and execution discipline.
Drive consistent field execution through structured agency engagement, territory planning, and rigorous pipeline management.
Build and deepen relationships with key agency partners, regional broker leaders, and national accounts operating within the Northeast.
Partner closely with underwriting, product, operations, and marketing to ensure aligned go-to-market execution and strong ease-of-business for agency partners.
Monitor and manage regional KPIs including new business premium, pipeline health, quote-to-bind performance, retention, and agency productivity.
Use data, dashboards, and Salesforce reporting to assess performance, identify gaps, and proactively adjust regional strategy.
Represent SageSure in the Northeast market through agency visits, regional meetings, industry events, and select conferences.
Ensure full adoption of Salesforce and other sales tools for activity tracking, pipeline visibility, and performance management.
Provide regular, executive-ready reporting on regional performance, market conditions, competitive dynamics, and growth opportunities.
Manage regional travel, entertainment, and event budgets with a clear ROI mindset.
Complete ad-hoc projects and support enterprise sales initiatives as needed to advance SageSure’s strategic priorities.
Maintain a strong field presence with regular, structured agency visits focused on production performance, growth opportunities, and ease-of-business improvements.
Ensure territory plans are in place and actively managed for each sales leader and key agency relationship.
Deliver consistent messaging on SageSure’s value proposition, appetite, and product strategy across the region.
Enforce disciplined use of Salesforce for tracking agency engagement, pipeline, and performance metrics.
Submit timely regional reports covering performance vs. plan, pipeline outlook, key wins/losses, and emerging risks or opportunities.