Top Tech Jobs & Startup Jobs in Chicago, IL

Manages accounting functions, ledger closings, reconciliations, journal vouchers, financial analysis, audit support, regulatory and GAAP reporting, insurance filings, consolidations, and process improvements. The role researches accounting guidance, documents controls, supports management reporting, participates in projects, and collaborates with financial management teams across affiliated insurance entities.

Leads and develops a DevOps engineering team responsible for CI/CD, infrastructure automation, cloud enablement, release engineering, developer tooling, and operational support. Drives AWS modernization, DevSecOps, Infrastructure as Code, observability, secure deployment standards, and continuous improvement. Partners with engineering, security, infrastructure, risk, and audit teams to improve reliability, compliance, release safety, and developer experience. Provides hands-on technical guidance, manages service quality and team execution, and participates in incident reviews, change governance, and operational improvement.

Develop and optimize content for financial professionals, translating complex topics into clear, engaging narratives. Own content initiatives from concept through publication, create thought leadership and sales enablement materials, repurpose content across channels, and evaluate performance. Coordinate campaigns, stakeholder reviews, approvals, timelines, and cross-functional meetings using project workflows such as Asana. Ensure content meets brand and regulatory requirements while identifying emerging marketing trends and improvement opportunities.

Leads advanced sales support for life insurance and annuity products by advising producers and field leaders on business succession, executive benefits, estate planning, taxation, and wealth transfer strategies. Provides case design, legal and technical guidance, client proposals, seminars, continuing education, training materials, and sales resources. Collaborates with product, underwriting, marketing, and field teams while managing external vendors and supporting Advanced Sales Department operations.

Supports financial professionals by creating and presenting comprehensive financial plans for individuals and business owners. Analyzes retirement, investment, tax, estate, insurance, education, and risk-management needs; coordinates specialists and client strategies; maintains documentation and compliance records; guides planning discussions; tracks follow-up actions; researches planning topics; and improves workflows, reporting, quality control, and technology adoption.

The Lead Underwriting Consultant oversees large life application underwriting, manages processes to meet financial objectives, and resolves complex underwriting issues.

Lead end-to-end IT risk-based audits, test ITGCs and key IT risks, manage continuous audit testing, support external audits, advise on new technologies (cloud, AI, cybersecurity), communicate findings to leadership, and lead team development and advisory projects across the enterprise.

Sell and recruit independent life insurance financial professionals, coach practice management, design and promote case solutions, meet territory sales goals, run regional marketing/study groups, and maintain compliance while traveling frequently to build producer relationships and grow Penn Mutual production.

External wholesaler responsible for recruiting and coaching independent financial professionals to sell Penn Mutual life insurance. Drive sales through prospecting, practice management, case design, and regional meetings; conduct up to 20 weekly face-to-face meetings, manage territory and T&E budget, ensure compliance with FINRA and state regulations, and support channel growth and company initiatives.

Design, build, and maintain advanced Workday reports, dashboards, and analytics to inform workforce planning and talent strategy. Partner with HR, HRIS, IT, and business leaders to define metrics, validate and govern data, perform deep-dive analyses, support Prism integrations, and deliver executive-ready insights, documentation, and training to enable data-driven HR decisions.