Software Engineer Jobs in Chicago, IL

About The Position

Requirements

• 3–6+ years of professional software engineering experience, with clear ownership of complex, production-critical systems.
• Strong command of TypeScript, Node.js, and REST API design, including debugging and integrating with external systems.
• Hands-on experience with AI-driven systems, including tuning agent behavior, refining prompts, and shaping workflow logic based on customer feedback.
• Exceptional communication and judgment, especially when balancing speed, reliability, and real-world constraints.
• Based in Chicago with willingness to travel 20–30% to customer sites.

Responsibilities

• Lead technical delivery for customer implementations, integrations, and workflow builds; owning projects from scoping through production rollout.
• Architect and build workflows that encode real customer processes, integrating directly with their systems and adapting to operational edge cases you uncover in the field.
• Develop core platform components and integration tooling that standardize common patterns, reduce one-off work, and help the team scale customer deployments efficiently.
• Navigate complex environments, fragmented data, and real-world constraints, and design solutions that work in practice, not just on paper.
• Provide field insight to product and engineering, shaping the roadmap with firsthand customer understanding.
• Travel 20–30% to customer locations and work in-person from our Chicago office.

Benefits

• Top-tier cash + equity
• Medical, dental, and vision coverage
• Fully covered lunches and dinners
• High ownership environment with rapid growth
• The opportunity to shape the future of AI in freight