Top Tech Jobs & Startup Jobs in Chicago, IL

The Sr Program Manager will lead cross-functional teams on complex insurance transformation projects, ensuring delivery on scope, schedule, and budget while optimizing business processes and modernizing enterprise systems.

Owns the technical roadmap for digital marketing and customer-facing experiences, including CMS, SEO, experimentation, analytics, personalization, and partner integrations. Translates marketing objectives into technical requirements, user stories, and scalable solutions; coordinates Marketing, Engineering, Architecture, and external partners; and supports backlog refinement, sprint planning, implementation, measurement, security, accessibility, compliance, and performance standards.

The Director of Compensation will lead compensation strategy and operations, including sales and incentive plan administration, executive compensation, market pricing, job leveling, offer design, benchmarking, and survey submissions. The role partners with senior stakeholders and assigned business groups, provides total rewards guidance, manages a small team, supports executive offers, and improves compensation policies and documentation. Workday Advanced Compensation experience is required, along with the ability to balance strategic initiatives and hands-on daily operations.

Owns website strategy and digital experiences across a multi-brand pet insurance portfolio. Leads website redesigns, martech integrations, SEO and AI search optimization, landing page development, conversion optimization, analytics, and performance reporting. Partners with marketing, content, design, product, IT, agencies, and vendors to improve traffic, engagement, quotes, enrollments, and revenue while managing website governance, technology roadmaps, and cross-functional initiatives.

Monitors U.S. and Canadian payroll compliance, regulations, tax filings, audits, controls, and employee pay accuracy. Investigates exceptions, manages corrective actions, supports SOX and regulatory audits, and coordinates payroll compliance for acquisitions and new entities. Maintains procedures, governance documentation, dashboards, and reporting while partnering with Legal, Finance, HR, vendors, and leadership to improve controls, reduce risk, and support payroll technology and transformation initiatives.

Owns the end-to-end business development pipeline for new insurance distribution partnerships, including prospecting, qualification, deal structuring, negotiation, and closing. Builds relationships with agencies, brokers, MGAs, affinity groups, and InsurTech platforms; tracks pipeline metrics; collaborates with internal teams to launch partnerships; and represents the company at industry events.

Lead accounting operations and a reporting team to improve AP, intercompany, investment, and banking workflows; drive reporting automation, controls, and UAT for system integrations; partner with FP&A, Procurement, IT, and external auditors; manage statutory and management reporting, reconciliations, accruals, and close processes while scaling processes and metrics across the organization.

The Product Analyst will analyze product performance, develop reports, and collaborate with stakeholders to enhance pet insurance offerings through data-driven insights.

Lead underwriting strategy and governance for Doubtless North American carriers, set underwriting philosophy and risk appetite, oversee delegated authority and MGA oversight, ensure regulatory compliance, monitor portfolio performance, implement controls and audits, and partner cross-functionally to drive disciplined, profitable growth.