FleetWorks · 1 month ago
Senior Software Engineer - Customer Platform
Chicago, IL
Full-time
Onsite
Mid, Senior Level
3+ years expFleetWorks is transforming the freight booking process with intelligent voice agents. In this role, you will lead technical delivery for customer implementations and build core platform components, while working closely with users to solve complex, real-world problems.
Transportation/Trucking/Railroad
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
Qualification
Required
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
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
Company
FleetWorks
Backed by Y Combinator Automating the 1B+ phone calls the freight industry makes every year
11-50 employees
H1B Sponsorship
FleetWorks has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (1)
Funding
Current Stage
Early StageCompany data provided by crunchbase