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Required Experience
Must have 5+ years of Property & Casualty underwriting experience — homeowners, dwelling property, personal lines, commercial property, or specialty/E&S lines.
Experience evaluating new business, renewals, endorsements, and policy changes
Experience working directly with independent insurance agents
Experience making underwriting decisions within established authority limits
**This is not an entry-level underwriting role. We are seeking an experienced underwriter who can independently evaluate risk, build agency relationships, and contribute to profitable portfolio growth.***
Our Hiring Process
At SSI, we're committed to hiring people into roles where they can thrive. As part of the interview process, please complete a briefCulture Indexsurvey. This 10-minute assessment isn't a test and there are no right or wrong answers. It simply helps us understand your natural strengths, communication style, and work preferences so we can make the best match for both you and our team.
Please note:Completion of the Culture Index survey is a required step in our hiring process. Applications will not be considered until the survey has been completed.
Take survey here:
The Opportunity
Most underwriting roles ask you to manage a book. This one asks you to shape one. At South Shore Insurance Underwriters , you won't just evaluate individual risks — you'll help define what a healthy, growing portfolio looks like, influence the relationships that drive it, and contribute to the strategy that sustains it.
We're looking for someone who sees the connection between a single underwriting decision and the long-term trajectory of a territory. Someone who brings intellectual curiosity to complex risks, builds genuine trust with agency partners, and isn't satisfied with just clearing the queue — they want to understand why the queue exists and how to make it better.
What You'll Own
Translate risk analysis into portfolio-level decisions — evaluating new business, renewals, endorsements, and complex submissions with an eye toward long-term profitability, not just individual acceptability.
Be the strategic underwriting voice for your territory — acting as a trusted advisor to agency partners, not just a decision-maker. Provide coverage guidance, creative solutions, and market insights that make agents want to bring you their best business.
Turn market intelligence into underwriting strategy — monitoring trends, competitor activity, and emerging risks, then connecting those signals to how you approach your book.
Identify growth opportunities others miss — recognizing patterns across submissions, agency relationships, and portfolio data that point to where profitable expansion is possible.
Drive continuous improvement — collaborating with leadership to sharpen underwriting processes, surface workflow inefficiencies, and contribute ideas that make the entire operation smarter.
Exercise confident judgment on complex and non-standard risks — knowing when to find a creative path forward and when to hold the line.
How You Think
This role is built for a specific kind of thinker. You might be the right fit if:
You zoom out before you zoom in — you can assess a single risk while keeping the portfolio implications in view.
You connect dots across information — an unusual submission, a shift in agent behavior, a regional weather pattern — and you know what those signals mean together.
You're energized by complexity, not slowed by it. Ambiguous risks are interesting puzzles, not obstacles.
You build real relationships, not transactional ones. Agents trust you because you bring them value, not just decisions.
You have a bias toward improvement — you naturally ask "why does this work this way?" and "what would make this better?" You balance conviction with humility — you're decisive, but you know what you don't know.
What You Bring
A track record of building strong agency relationships and delivering decisions agents rely on.
Sharp analytical instincts paired with clear, confident communication — written and verbal.
Comfort working independently in a remote environment, with the discipline to manage competing priorities without losing quality.
CPCU, CIC, AINS, CRM, or other insurance designations are a plus — but intellectual curiosity matters more than credentials.
Excess & Surplus Lines experience is valued but not required.
Bachelor's degree in Business, Risk Management, or a related field preferred.
Why South Shore
We believe our success starts with our people. We are committed to creating an environment where coworkers feel valued, supported, and empowered to make a meaningful impact. In return for your hard work, dedication, and commitment to excellence, we provide opportunities to grow professionally, contribute innovative ideas, and build a rewarding career in a collaborative and supportive environment. Our coworkers enjoy competitive compensation, comprehensive benefits, generous paid time off, wellness and mental health resources, paid parental leave, and a 401(k) with company matching contributions. We recognize that work is only one part of a fulfilling life and strive to support the well-being of our coworkers both inside and outside the workplace. Our culture is built on trust, transparency, teamwork, and continuous improvement. We encourage coworkers to act with integrity, embrace challenges and innovation, and work together by supporting one another and sharing success. At South Shore Insurance, you are more than an employee—you are a valued member of a team that invests in your growth, celebrates your contributions, and empowers you to help shape the future of our organization.
If you're looking for a role where your thinking shapes outcomes beyond the next submission — we'd love to talk.
SSIU is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, or any other protected status.