Staff Software Engineer

Location: Chicago, IL, United States

Industry: Transportation & Logistics

Posted: 2026-05-11

Contact: Ethan Hudson

Email: ehudson@oprecruiting.comPhone: 13176505687

Job Title: Staff Software Engineer

Location: Chicago, ILAbout the Opportunity Join a high-growth, venture-backed fintech organization as a foundational member of our engineering team. We are developing an AI-native financial operating system designed to modernize complex industrial supply chain transactions. Having recently secured significant pre-seed funding and already generating revenue, we are scaling our platform to meet overwhelming enterprise demand. This is a rare opportunity to work directly with a founding team of industry veterans from top-tier disruptors (Uber, Groupon, Convoy) to architect the future of B2B financial infrastructure.

Responsibilities: End-to-End Development: Design and deploy mission-critical features across the entire stack, spanning complex data ingestion engines to intuitive user interfaces. System Architecture: Architect and maintain scalable, high-velocity infrastructure designed to minimize technical debt and operational overhead. AI-Driven Velocity: Lead the integration of advanced AI development workflows (LLMs, automated testing, and code generation) to accelerate product delivery cycles. Technical Strategy: Partner closely with the executive leadership team to define the long-term technical roadmap and foundational engineering standards. Product-Market Fit: Interface directly with enterprise customers to translate complex workflows into seamless product experiences. Cultural Leadership: Establish best practices for code quality and engineering excellence as the organization scales from its early stages.

Requirements: (must-have) Senior-Level Expertise: Minimum of 7+ years of professional full-stack development experience. Modern Technical Stack: Advanced proficiency in Python, TypeScript, React, SQL, and cloud infrastructure. Startup DNA: Proven track record of building 0-to-1 products and scaling early-stage SaaS platforms. AI Fluency: Deep experience utilizing AI development tools to optimize workflows and increase engineering output. Ownership Mindset: Exceptional reliability and a bias toward clarity and technical ownership in an ambiguous environment. Preferred

Qualifications: (nice-to-have) Experience in fintech, logistics, or supply chain technology. Previous experience as a founding engineer or early employee at a high-growth startup.

Compensation & Benefits: Highly competitive base salary. Significant early-stage equity package. Comprehensive healthcare and benefits. The chance to shape the DNA of a company as the second engineering hire.#LI-ML1