Top Tech Jobs & Startup Jobs in Chicago, IL

Owns an assigned territory and production target by growing independent agency business. Builds agency relationships through field visits, training, and consultative selling; drives adoption of Branch’s quoting platform; improves quote quality and agency activation; manages pipeline and production performance; addresses objections; and provides competitive and market insights to cross-functional teams.

Own the end-to-end statutory financial reporting process for a property and casualty insurer, including quarterly and annual NAIC filings, RBC analysis and forecasting. Analyze financial outcomes, maintain reporting processes, develop internal control testing frameworks, support audits and reconciliations, and collaborate with Finance, Compliance, Legal, Insurance, actuarial, reinsurance, and Data teams on regulatory and reporting needs.

Leads insurance financial reporting, including statutory statements, quarterly and annual NAIC filings, RBC analysis, and forecasting. Maintains financial processes, controls, audit-ready documentation, cash reconciliation procedures, and internal control testing. Analyzes financial results and collaborates with Finance, Compliance, Legal, Insurance, actuarial, reinsurance, and Data Office teams to support accurate reporting, regulatory compliance, state expansion, and improved financial transparency.

Own a defined territory and production target by growing independent agency business. Build agency relationships, conduct in-person visits and training, drive adoption of Branch’s quoting platform, improve quoting quality, activate producing agencies, address objections, track premium and policy performance, and provide competitive and market feedback. The role requires self-directed field sales, consultative selling, and cross-functional collaboration with Marketing, Product, Underwriting, and Operations.

Leads Branch’s field sales organization responsible for growing agency-distributed business and achieving aggregate production targets. Builds and coaches Territory Managers, establishes territory and agency prioritization standards, manages forecasting and pipeline performance, and develops scalable sales playbooks. Partners with Finance, Marketing, Product, Underwriting, and Operations to remove growth barriers. Travels regularly with territory leaders to coach agency visits, manage strategic relationships, gather market intelligence, and improve CRM, quoting, onboarding, and agency-facing workflows.

Own the full enterprise sales cycle for strategic insurance agency and institutional technology partnerships. Build pipeline, navigate technical and executive buying committees, develop ROI cases, negotiate agreements, and close complex platform deals. Partner with Product and Engineering on integrations, manage post-launch adoption and expansion, and maintain accurate forecasts in HubSpot. Serve as an internal expert on enterprise sales strategy while coordinating onboarding and go-live with implementation, account management, and customer success teams.

Own personal lines insurance forms, endorsements, filings, regulatory responses, and ongoing compliance reviews across multiple states. Test policy output, rating tables, and formatting against approved filings; maintain test plans, test cases, and defect tracking. Partner with Product, Underwriting, Pricing, Actuarial, Claims, Technology, and Analytics teams to deliver changes and automate quality assurance. Interpret policy language, document updates, manage parallel workstreams, and identify discrepancies between filed and shipped products.