Senior Underwriter — Strategic Growth & Risk

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.***
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 w