Top Tech Jobs & Startup Jobs in Chicago, IL

Lead strategy and execution for paid search and programmatic user acquisition (Google UAC primary). Manage DSPs and networks, own testing roadmap, translate MMP/backend data into performance narratives, collaborate with Analytics, Creative, and Growth, and eventually manage and develop a direct report.

Lead Underdog's offline media strategy across TV, CTV/OTT, radio/audio, and out-of-home. Own media budget and agency relationships, optimize for incrementality and efficiency, define KPIs and measurement frameworks, partner with Data Science and cross-functional teams, and scale acquisition through testing, creative, and regional strategies.

Manage treasury operations including customer fund segregation, cash positioning, wire transfers, and regulatory reporting in a fast-paced environment.

Lead and scale Underdog's tax function as the primary internal tax resource. Manage federal, state, and local tax compliance; prepare in-house filings and ASC 740 tax provision; partner with Product/Engineering/Data to build customer-facing tax capabilities; coordinate R&D credit analysis; manage external advisors and audits; research tax implications of new products; and build scalable tax processes, controls, and reporting.

Lead execution of Underdog's rebrand across social, paid, email, CRM, partnerships, and product. Own end-to-end campaign design, produce high-impact and UGC-style assets, collaborate with Marketing and Product, maintain the Frontify brand library, contribute creative direction and copy, and manage multiple projects to deadlines with high ownership.

Own and scale the core betting experience across mobile and web using React Native. Diagnose and fix critical client issues, lead cross-platform design reviews, partner with backend/product/design, use analytics to validate changes, coach engineers, and drive reliability, performance, and developer-velocity initiatives.

Run reactive stunt marketing end-to-end: spot cultural moments, pitch and build stunts rapidly, execute and capture content, distribute to high-impact meme/accounts, coordinate cross-functionally, and track performance (EMV, impressions, sentiment). Must already have an authentic online presence and feel for internet culture.

Run Underdog's local go-to-market activations: book bars, coordinate tailgates and street stunts, secure vendor/venue deals, manage budgets and timelines, travel to represent the brand, and use AI tools to speed logistics while owning on-site problem-solving and relationships.

Lead paid social user acquisition for a consumer app: own strategy, execution, testing, and optimization across Meta and TikTok. Partner with analytics, creative, and platform account teams to validate attribution, forecast, and scale growth while running a structured experimentation roadmap. Monitor trends and translate performance data into executive-ready recommendations. WOOF WOOF

Lead marketing operations by building scalable systems, processes, and playbooks to plan and execute campaigns. Manage cross-functional coordination, timelines, launch readiness, measurement frameworks, dashboards, budget and resource planning, and continuous process improvement to ensure campaigns launch and perform effectively.