Jobs at FairSquare

Work directly with senior leadership to evaluate reinsurance, MGA, and program business deals. Convert broker submissions into decision-ready packages, build and audit financial models, draft deal memos and diligence requests, manage pipeline and document flow, support contract and program buildout, and use AI tools to accelerate analysis while verifying outputs against source documents.

Lead analytics effort to collect, clean, integrate, analyze data and build/monitor predictive models (including recommendation systems). Partner with stakeholders, mentor data scientists, perform EDA, root cause analysis, and consult on analytics-driven strategies.

Lead creation and execution of FairSquare's procurement function: design workflows, negotiate and manage vendor contracts, coordinate cross-functional reviews (Legal, Compliance, InfoSec, Finance), maintain vendor portfolio and renewals, and implement procurement policies and cost-saving strategies.

Hands-on senior writer producing high-performing copy across print and digital channels (direct mail, web, email, SMS, social, video). Use audience data and AI/SEO tools to inform writing, support brand strategy, mentor junior writers, ensure brand consistency, collaborate cross-functionally, and deliver projects on time.

The role involves managing commercial transactions and compliance, drafting agreements, advising business units, supporting regulatory compliance, and maintaining contract lifecycles.

The Director of Data Engineering leads the data engineering team, designs scalable data infrastructure, ensures data quality, and collaborates with cross-functional teams to drive data initiatives.