Top Tech Jobs & Startup Jobs in Chicago, IL

Hands-on technical leader accountable for architecture, design, and delivery of core insurance platforms (policy, claims, portals, web, mobile). Leads and mentors engineers, conducts code and design reviews, oversees CI/CD and Azure-based DevOps, champions engineering standards, and partners with Product and Operations to translate business needs into secure, scalable solutions while managing technical debt and platform modernization.

Lead design, build, deploy, and operate agentic AI solutions using Microsoft Copilot Studio, Power Platform, Dynamics 365, and Azure services. Own reference implementations, CI/CD, integrations (Dataverse, REST APIs), monitoring, compliance, and mentor engineering teams while collaborating with product, data, security, and architecture stakeholders.

Lead portfolio-level performance marketing for multiple pet insurance brands. Shape acquisition strategy across search, social, affiliate/aggregator and emerging channels; analyze CAC, LTV, ROI; optimize channel mix, budgets, targeting, creatives and funnels; partner with analytics, agencies, and stakeholders to improve attribution, forecasting, and incrementality testing; identify growth opportunities and leverage AI-driven marketing innovations.

Part-time in-office Office Manager responsible for front-of-house visitor experience, meeting coordination and catering, office operations and supplies, liaison with property management, mail and delivery handling, onboarding support, and event execution. Acts as central point of contact for employees, visitors, vendors, and leadership while maintaining confidentiality and professionalism.

Lead and execute high-visibility brand and motion design across a portfolio of pet insurance brands. Create strategic visual concepts for digital, print, social, web, email, and paid channels. Mentor junior designers, partner with stakeholders, present creative rationale, and maintain brand consistency while managing multiple projects and timelines.

The Marketing Data Analyst will analyze performance data across marketing and sales channels, develop dashboards, and provide insights to improve customer engagement and ROI.

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.

Manage and develop the accounting team, ensure accurate financial records and reconciliations, support audits and regulatory reviews, document policies, drive process improvements, and collaborate cross-functionally on financial and tax matters.