Senior Software Engineer, Sonoma

Hiring: Senior Software Engineer
The U.S. freight industry moves trillions of dollars in goods every year, yet much of the operational infrastructure still relies on phone calls, emails, spreadsheets, and fragmented workflows.
We're building AI-powered systems that modernize how freight is booked, coordinated, and managed — replacing manual operations with intelligent automation and voice-driven workflows.
We're looking for a Senior Software Engineer to join our engineering team in Chicago.
This is a highly technical, high-ownership role where you'll work directly with operational environments, build production systems, and solve complex real-world problems at the intersection of AI, software, and logistics.
What You'll Do:
• Lead end-to-end development of customer-facing features, integrations, and internal platform systems
• Architect and build scalable workflows that integrate with customer operations and third-party platforms
• Develop reusable infrastructure and tooling that improve deployment speed and reliability
• Work closely with customers and internal teams to understand operational challenges and rapidly ship solutions
• Contribute to product direction and technical strategy through direct field and customer insight
• Collaborate in-person from our Chicago office and travel occasionally to customer sites ******%)
What We're Looking For:
• 5+ years of professional software engineering experience building and owning production systems
• Strong experience with TypeScript, Node.js, and REST API design
• Experience integrating with external systems and debugging complex workflows in production environments
• Hands-on experience with AI-driven systems, LLM workflows, prompt engineering, or agent-based architectures
• Strong product intuition, communication skills, and ability to thrive in ambiguous environments
• Based in Chicago or willing to relocate
What We Offer:
• Competitive salary + equity
• Medical, dental, and vision coverage
• Daily meals provided
• High ownership and fast execution environment
• Opportunity to help shape the future of AI in logistics and operations