Top Tech Jobs & Startup Jobs in Chicago, IL

Leads analytics strategy for Zip’s emerging financial products, from market sizing and launch readiness through adoption, retention, risk, and unit economics. Partners with Product, Finance, Risk, and Operations leaders to define metrics, build scalable dbt models and reporting frameworks, analyze customer and portfolio behavior, and guide strategic decisions. Establishes SQL and analytics standards, mentors analysts, and translates complex findings into recommendations for executives.

Own Zip’s affiliate and partner marketing programs end to end, including strategy, partner negotiations, campaign launches, optimization, performance reporting, and revenue growth. Manage advertiser relationships, coordinate cross-functional activation, identify monetization opportunities, and advise leadership using attribution and performance insights. The role requires strong commercial judgment, affiliate network expertise, and ownership of revenue targets across fintech, e-commerce, or marketplace channels.

Own analytical strategy and develop AI/ML models for Zip’s financial products, including cash and rent advances. Lead ambiguous 0-to-1 initiatives using bank transaction data, establish evaluation frameworks, guide risk and growth decisions, and deliver models from experimentation through production. Provide technical direction to data scientists, mentor junior team members, collaborate with engineering, and advise senior stakeholders on model trade-offs. The role requires strong financial services, statistical, research, and machine learning expertise.

Leads Zip’s US external communications strategy across corporate, consumer, executive, financial, media, and crisis communications. Develops corporate narratives, manages top-tier media relationships, supports public-company disclosures and potential Nasdaq listing activities, advises executives, oversees issues management, coordinates global communications, and manages agencies. Partners extensively with Investor Relations, Legal, Finance, Marketing, Product, and regional teams to strengthen reputation and business impact.

Leads Zip’s highest-priority cross-functional programs, special projects, integrations, and organizational transitions. Translates enterprise strategy into execution through roadmaps, governance, risk management, decision-making, executive communication, and measurable outcomes. Partners across Product, Engineering, Finance, Legal, People, Commercial, and Delivery, while improving repeatable program-management practices using Jira, Confluence, AI, and automation.

Lead corporate development activities, including acquisitions, strategic investments, market assessments, valuation, financial modeling, due diligence, deal structuring, and transaction execution. Prepare board and executive materials, coordinate advisers and stakeholders, and support strategic reviews and capital allocation decisions. The role requires financial services experience, advanced transaction modeling, commercial diligence expertise, and the ability to manage complex M&A workstreams autonomously.

Staff Engineer leading architecture and technical direction for Zip’s real-time payments and money-movement platform. The role designs reliable distributed systems, leads complex cross-team initiatives, mentors senior engineers, and improves scalability, performance, and engineering standards. It also drives responsible AI adoption across engineering through tooling, workflow integration, governance, measurement, and production-grade AI capabilities. Candidates need extensive backend, payments or correctness-critical systems, cloud, system design, and technical leadership experience.

Build and own scalable payments infrastructure for card issuing, transaction processing, and settlement. Design reliable integrations with Stripe, banking partners, and internal platforms using .NET, C#, Azure, DDD, CQRS, and event-driven architectures. Improve system reliability, observability, performance, security, and compliance while mentoring engineers and contributing to technical direction. Apply AI-assisted development across coding, testing, debugging, and engineering workflows.

Partner with the CEO and senior leaders to shape enterprise priorities, structure complex decisions, drive strategy execution, establish KPIs, resolve cross-functional trade-offs, and lead high-impact initiatives. Serve as a trusted advisor and operator who extends the CEO’s impact, creates organizational alignment, and improves workflows through AI and emerging tools.

Assistant General Counsel leading corporate transactions, M&A, strategic partnerships, complex financing, securities compliance, public company disclosures, and corporate governance. The role advises executives, manages outside counsel, develops scalable legal processes, evaluates AI-enabled legal workflows and governance risks, and mentors junior legal professionals. Candidates need 12+ years of corporate law experience, a J.D., active U.S. state bar membership, and substantial M&A, structured finance, securities, and executive counseling expertise.