Head of Regional Sales (Northeast)

Who We Are

At SageSure, we are committed to providing innovative solutions for property insurance in some of America’s most challenging markets. As one of the leading property insurance providers in the U.S., we foster a culture of collaboration, innovation, and data-driven decision-making. Our Go-To-Market (GTM) teams are at the forefront of driving growth, and we are looking for a strategic leader to own regional performance and execution. If you are a proactive leader passionate about sales, marketing, and delivering results, we invite you to join our dynamic team.

Role Overview

As the Head of Regional Sales, Northeast, you will own the overall sales performance, execution discipline, and agency relationships across one of SageSure’s most complex and strategically important regions. 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.

You will lead and develop a high-performing regional sales team, partner closely with underwriting, product, operations, and marketing, and serve as the senior field leader responsible for translating enterprise strategy into measurable regional results. Success in this role requires strong market knowledge, disciplined field execution, data-driven decision-making, and the ability to influence both internal and external stakeholders.

What you’d be doing

• 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.

Key Operational Expectations

• 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.

We’re looking for someone who has

• 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).

Highly preferred candidates also have

• 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.

About SageSure:

Named among the Best Places to Work in Insurance by Business Insurance for four years in a row (2020-2023), SageSure is one of the largest managing general underwriters (MGU) focused on catastrophe-exposed property in the US. Since its founding in 2009, SageSure has experienced exceptional growth while generating underwriting profits for carrier partners through hurricanes, wildfires, and hail. Available in 16 states, SageSure offers more than 110 home, flood, and commercial products on behalf of its highly rated carrier partners. Today, SageSure manages more than $3.2 billion of inforce premium and helps protect more than 970,000 policyholders.  

 We have more than 1,000 employees in a distributed workforce environment across 12 offices—Fairfield, CA; Mountain View, CA; Cheshire, CT; Jacksonville, FL; Tallahassee, FL; Tampa, FL; Chicago, IL; Jersey City, NJ; Marlton, NJ; Cincinnati, OH; Houston, TX; Sheboygan, WI—who are tackling the industry’s toughest challenges.     

SageSure is a proud Equal Opportunity Employer committed to building a workforce that reflects the spectrum of perspectives, experiences, and abilities of the world we live in. We recognize that our differences make us strong, and we actively seek out diverse candidates through partnerships with organizations, institutions and communities that represent various backgrounds. We champion belonging and inclusion for all identities, including, but not limited to, race, ethnicity, religion, sexual orientation, age, veteran status, ability status, gender, and country of origin, striving to create a culture where all individuals feel valued, respected, and empowered to bring their authentic selves to work. 

Our nimble, highly responsive culture nurtures critical thinkers who run toward problems and engineer solutions. We relentlessly pursue better outcomes by investing in the technology, talent, and tools that position us to succeed in demanding markets. Come join our team! Visit sagesure.com/careers to find a position for you. 

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