Top Tech Jobs & Startup Jobs in Chicago, IL

Own and execute paid search and intent-driven acquisition across Google Ads and Microsoft/Bing, managing budgets, bidding, and performance vs. CPA/ROAS targets. Lead experimentation, creative testing, measurement integration, and compliance for a regulated vertical. Partner cross-functionally with Creative, Lifecycle, Product, Data, Finance, and Media Ops to scale first-time shopper acquisition, ensure tracking and reporting quality, and document SOPs.

Lead Hagerty's EPMO for the APEX Duck Creek implementation: own program financials, vendor and contract oversight, risk/issue management, status and change control, and build a permanent Center of Excellence for program and project management while managing and developing the EPMO team and executive governance reporting.

Lead and scale the marketing organization to drive payer adoption, patient demand, and brand positioning. Own brand, product marketing, commercial enablement, analytics, and marketing operations. Translate clinical outcomes and value-based care data into compelling narratives for health plans, build measurement systems, and partner cross-functionally to accelerate enterprise growth.

Design and deliver VMS and RPO technical solutions (Fieldglass/Beeline/VNDLY), lead requirements, integrations, testing and deployment, produce technical documentation, provide technical governance, coach analysts, and advise stakeholders on architecture and industry trends.

Research and resolve title issues for REO and refinance transactions, review and grade title commitments, prepare curative documents and claim packages, communicate status to stakeholders, enter data into platforms, monitor resolutions, and escalate potential losses.

Own and improve Command Center's core onboarding, activation, and enrollment workflows. Define product vision and roadmap, partner cross-functionally, drive digital transformation away from manual processes, measure impact with data, and use AI-assisted practices to accelerate delivery while enabling other teams to build on the platform.

Own technical execution of new client onboardings and offboardings: deploy core services, manage access and migrations (Microsoft/Google), document in ConnectWise/ITGlue/Rocketlane, monitor project progress, support onsite techs, execute decommissions, and improve onboarding processes to meet timelines and KPIs.

Design, build, and operate a next-generation CDP/messaging platform at scale. Define infra topology, scaling, blast-radius limits, and safety guardrails for AI agents. Own reliability, capacity, cost, security boundaries, incident leadership, and author self-verifying runbooks and checks so automation can operate safely.

Lead development and execution of training and organizational change management strategies for federal digital transformation. Conduct training needs analyses, design instructional materials, facilitate stakeholder workshops, collaborate with technical teams to translate complex IT concepts, author RFI/RFP content, build customer relationships, and measure effectiveness to refine programs.

Lead global SRE team to design, implement, and operate scalable, highly available cloud infrastructure. Drive observability, automation (IaC/CI-CD), cost optimization (FinOps), security hygiene, and post-incident improvements while remaining hands-on and exploring AI tooling for reliability.