Top Tech Jobs & Startup Jobs in Chicago, IL

Leads cross-functional technical programs from planning through launch, including carrier integrations, partner launches, internal tooling, and platform improvements. Partners with Engineering, Product, Data, Operations, and external stakeholders to establish milestones, manage risks and dependencies, communicate program health, make technical tradeoffs, and improve execution through retrospectives and success metrics.

Owns Ethos’s insurance marketing compliance review function, including AI review-tool administration, automation strategy, human oversight, regulatory standards, disclosures, audit trails, and review operations. Personally handles complex reviews while improving intake, SLAs, quality, throughput, and reporting. Partners with Marketing, Product, Legal, Engineering, Data, carriers, and regulators; supports filings and exams; and builds the function by hiring and managing a compliance analyst.

Owns strategy, execution, budgeting, measurement, reporting, and optimization for Ethos’s Streaming TV/OTT acquisition program. Partners cross-functionally with Creative, Analytics, MarTech, Product, and Finance; manages agencies and media buying; improves attribution, targeting, bidding, and incrementality testing; evaluates vendors and tools; presents recommendations to executives; and identifies scalable growth opportunities across offline and emerging channels.

Lead the Consumer Product team’s strategy, roadmap, and execution for Ethos’s digital life insurance experience. Manage, mentor, and grow product managers while driving consumer acquisition, onboarding, conversion, experimentation, and satisfaction. Partner with Engineering, Design, Data Science, Marketing, and Actuarial teams to deliver accessible, simple products and identify new insurance opportunities. Communicate strategy and results to executives and drive sustainable growth through data-informed product decisions.

Own financial strategy, planning, forecasting, and performance management for the go-to-market business. Partner with Marketing, Product, Sales, and Operations on unit economics, customer acquisition, profitability, growth efficiency, new products, customer segments, and strategic initiatives. Develop financial metrics, deliver actionable insights, evaluate new business opportunities, and support executive decision-making. The role also interfaces with external partners through corporate development and business development activities.

Develops direct-response scripts for TV, radio, podcasts, UGC, paid social, and influencer campaigns. Creates compelling hooks, narratives, and calls to action for 15- and 30-second formats; adapts concepts across platforms; supports production shoots; collaborates with creative, production, editing, and performance marketing teams; and uses performance insights and AI tools to improve creative output.

Lead the design and operation of a cloud-first IT environment, including SaaS administration, endpoint management, security, automation, email platforms, and AI-powered workflow agents. The role drives cross-functional IT projects, mentors team members, maintains standards and documentation, resolves complex escalations, and supports onboarding and escalated tickets. Key responsibilities include managing Google Workspace, Proofpoint, Slack, Okta, Jamf, Intune, and related systems while improving reliability, security, and operational efficiency.

Lead and scale Ethos's Final Expense sales organization: set strategy and KPIs, recruit and train licensed agents and managers, build playbooks and coaching programs, partner with Product, Marketing, and Finance on tests, staffing, and compensation, and drive a data-driven, high-performance culture to meet revenue and productivity goals.

Investigate offline and direct mail channel performance, attribution, vendor data, and measurement methodologies. Build response, lift, allocation, and regression models; manage direct mail testing data pulls and mail merges; create KPI dashboards; and communicate actionable recommendations to marketing stakeholders. The role requires proactively identifying opportunities, validating data and vendor claims, and translating complex analytical findings into business decisions.

Own product analytics strategy across high-impact product areas, identifying growth opportunities and shaping product and executive decisions. Lead experiment design, guardrails, causal inference, power analysis, and cross-experiment interpretation. Validate and improve AI-generated analyses, develop customer and business insights, and connect patterns across data sources. Partner with product, design, engineering, and leadership while raising standards for analytical rigor and AI-assisted workflows.