Top Tech Jobs & Startup Jobs in Chicago, IL

Own Flex’s go-to-market strategy and commercial execution for the auto loan vertical. Build executive-level relationships, develop pipeline, negotiate and close complex partnerships, and guide agreements through technical deployment and launch. Collaborate with Product, Engineering, Marketing, Finance, Legal, and Compliance to shape the offering, translate market feedback into improvements, and establish a repeatable sales motion. This zero-to-one role also requires developing scalable processes and using AI-assisted sales tools to improve pipeline and deal performance.

Support Revenue Strategy and Operations by designing and documenting commission capitalization under ASC 340-40. Build recoverability calculations, amortization schedules, audit-ready documentation, and repeatable processes tied to compensation outputs. Model 2027 sales compensation plans, including quotas, accelerators, caps, pay curves, and SPIFFs. Analyze plan costs, run leadership scenarios, prepare rollout materials, and fulfill revenue analytics requests using financial and sales data.

Designs, builds, and scales backend services and integrations for payments, billing, identity, and partner connectivity. Sets technical vision and architecture for distributed systems, leads cross-team delivery, manages production rollouts, builds fault-tolerant services and data pipelines, and mentors engineers. The role partners with product, design, and engineering teams to deliver frequent, reliable improvements for Flex’s rent payment platform.

Design, build, and scale backend services and integrations for payment, billing, identity, and partner systems. Own API scoping, design, implementation, deployment, and production operations with minimal oversight. Build fault-tolerant systems, data pipelines, and scalable architectures while collaborating with product, design, engineering, and external partners. Contribute to reliability monitoring, observability, automation, technical standards, and mentoring in a distributed team.

Build and own full-stack MarTech services, scalable APIs, event-driven systems, data pipelines, and customer-facing web experiences. Integrate advertising, analytics, messaging, and marketing platforms while supporting attribution, identity resolution, experimentation, acquisition, and retention. Collaborate cross-functionally with marketing, product, data, design, and engineering teams to launch measurable growth initiatives. Mentor engineers and establish technical best practices across high-scale marketing infrastructure.