Financial & Deal Analyst, Reinsurance & MGA (AI-First)

FairSquare•San Diego, CA

6d•$95,000 - $125,000•Hybrid

About The Position

This is a hands-on analytical role on a lean, AI-first, fast-growing specialty reinsurance platform. The Financial & Deal Analyst will work directly with senior leadership on live deals from submission to contract. The role involves analyzing and evaluating real capital-at-risk transactions, with a focus on a verification-first, AI-leveraged approach. This is not a narrow actuarial, project management, or executive assistant role. The ideal candidate is quantitatively strong, organized, a clear writer, comfortable with ambiguity, and eager to learn a technical market quickly. An insurance background is not required; the focus is on thinking ability and learning speed.

Requirements

Highly analytical and quantitatively strong, comfortable with financial logic.
Strong in Excel and able to build clean, auditable models.
Clear, concise, and effective writer.
Highly driven, proactive, and comfortable taking ownership of ambiguous problems.
Able to learn technical concepts quickly and ask good questions.
Organized enough to keep multiple live workstreams moving at once.
Able to form a view from incomplete information and show assumptions clearly.
Detail-oriented without losing the commercial big picture.
Discreet with confidential and market-sensitive information.
Proficient with AI tools for analysis and drafting, with a commitment to verifying output.
Strong quantitative degree or equivalent demonstrated analytical ability (finance, economics, actuarial science, statistics, applied mathematics, engineering, operations research, data science, computer science, or related).
Strong Excel and financial modeling skills.
Excellent written communication skills.

Nice To Haves

1-5 years of analytical experience preferred.
Exposure to insurance, reinsurance, MGA/program business, finance, credit risk, banking, consulting, or analytics.
Python, SQL, Power BI, Claude Code, Codex, GitHub Copilot, or workflow-automation experience.

Responsibilities

Turn raw broker submissions into clean, decision-ready packages by digesting decks, loss runs, exposure data, and exhibits.
Build financial models to evaluate deals, including premium, expected loss, expenses, collateral, downside scenarios, and underwriting margin.
Rebuild numbers from source documents, flag discrepancies or missing information, and bring issues to the team's attention.
Draft deal memos, broker emails, diligence requests, internal summaries, board materials, and contract comment trackers.
Support contract review and program buildout, including reinsurance terms, collateral and reporting provisions, claims provisions, fronting carrier diligence, reinsurer materials, underwriting guidelines, and exposure tracking.
Manage the deal pipeline, tracking status, deadlines, dependencies, open questions, and next steps.
Own the knowledge base and document flow to ensure the team operates from a single source of truth.
Utilize AI tools (e.g., ChatGPT, Claude) and Excel for analysis, drafting, and research, followed by verification of the output.