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Assistant Vice President, Commercial Sales

SageSure
Cheshire, CT Full Time
POSTED ON 1/5/2026
AVAILABLE BEFORE 2/18/2026
Overview:

At SageSure, we are redefining the future of property insurance as the leading Managing General Underwriter (MGU) in the U.S. Built on innovation and collaboration, we partner with carriers, producers, and communities to deliver solutions that expand access and create stability in challenging markets. We are now scaling our innovative approach into Commercial Lines, with an ambitious goal to reach $1B in premium by 2030. To achieve this, we seek a visionary leader to shape and lead our Commercial Sales team.

The Opportunity:

As Assistant Vice President of Commercial Sales, you will set the strategic direction for SageSure’s growth in the commercial space. You will define strategy, lead a high-performing team, and serve as the primary representative of SageSure’s Commercial business in the industry. In close partnership with the President of Commercial, you will accelerate market entry, strengthen distribution partnerships, and drive adoption across our full commercial portfolio—including SageSure Preferred Signature products, GeoVera Commercial Property, and Expanded Markets offerings.

This is a unique opportunity to lead in a high-growth environment, where your impact will be measured by innovation, market expansion, and execution excellence.

What you’d be doing:

  • Strategic Leadership : Develop and communicate SageSure’s commercial growth vision, market positioning, segmentation, and distribution strategy for small business and middle-market segments, in collaboration with the President of Commercial and executive leadership.
  • Growth Focused : Lead the Commercial sales & marketing strategy team, setting ambitious yet achievable targets for new business premiums, retention, and profitability.
  • Market Representation: Serve as the face of SageSure’s Commercial business, cultivating trusted relationships with national partners and industry stakeholders.
  • Distribution Expansion : Grow SageSure’s presence among wholesalers, aggregators, networks, and clusters, while deepening partnerships with middle-market brokers.
  • Product Adoption : Drive trial, awareness, and adoption of all SageSure commercial offerings, ensuring producers are engaged, and programs focus on profitable growth.
  • Market Intelligence : Own commercial market analysis, competitive intelligence, and producer feedback, partnering with Market Strategy & Insights and CX teams to inform decision-making.
  • Cross-Functional Collaboration : Work closely with Product, Underwriting, Carrier Operations, Software, CX, and Marketing to deliver innovative, producer-friendly products and experiences.


We’re looking for someone who has:

  • Minimum 12 years of progressive leadership experience in commercial insurance, with expertise in small-to-middle market property, including admitted and E&S markets.
  • Demonstrated success in building and executing strategies that deliver sustainable growth.
  • Established relationships and credibility with commercial national brokers, wholesalers, and aggregators.
  • Strong commercial acumen, including expertise in sales, capacity management, producer economics, and middle-market dynamics.
  • Data-driven decision-making skills, with proficiency in dashboards, performance metrics, and win/loss analysis.
  • Exceptional executive presence and communication skills, with the ability to influence senior leaders and represent SageSure externally.
  • Proven experience leading organizations through growth, transformation, and change.


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 markets 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 50 competitively priced home, flood, earthquake, and commercial products on behalf of its highly rated carrier partners. Today, SageSure manages more than $1.9 billion of inforce premium and helps protect 640,000 policyholders.

SageSure has more than 1000 employees working remotely or in-office across nine offices: Cheshire, Connecticut; Chicago, Illinois; Cincinnati, Ohio; Houston, Texas; Jersey City, New Jersey; Mountain View, California; Marlton, New Jersey; Tallahassee, Florida; and Seattle, Washington.

SageSure offers generous health benefits and perks, including tuition reimbursement, wellness allowance, paid volunteer time off, a matching 401K plan, and more.

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.

Salary.com Estimation for Assistant Vice President, Commercial Sales in Cheshire, CT
$277,877 to $374,535
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