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Senior Software Engineer - Forward Deployed

FleetWorks - Chicago | OnSite | San Francisco

Posted Jun 10, 2026

Benefits

Parental leave
Not verified
Non-birth-parent leave
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Family-building benefits
  • Fertility benefits: Not verified
  • Adoption assistance: Not verified
  • Surrogacy assistance: Not verified
Mental health support
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Relocation assistance
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Childcare support
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Learning budget
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Verification
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Salary
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401(k) match
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Market context

U.S. role benchmark (BLS OEWS)
$116,543 U.S. median for this role
Projected growth (BLS Employment Projections)
+9.8% - Much faster than average

Matched to SOC 15-1252 - Software Engineering aggregate by role bucket.

Source: U.S. Bureau of Labor Statistics, OEWS, May 2024 and Employment Projections, 2024-2034.

Role

Role function
Engineering From the posting source checked Jun 20, 2026
Seniority
Senior From the posting source checked Jun 20, 2026
Work mode
Onsite From the posting source checked Jun 20, 2026
In-office days
5 days From the posting source checked Jun 20, 2026

Schedule

Shift type
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Weekend work
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Company

Company stage
Series A From the posting source checked Jun 20, 2026

Application

Cover letter
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Assessment
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Deadline
Not stated

Where they hire

State eligibility is not yet verified.

About this role

Senior Software Engineer - Forward Deployed Chicago | OnSite | San Francisco Every year, companies spend over a trillion dollars moving freight across the U.S. but the system for matching trucks with jobs is still slow, manual, and fragmented. FleetWorks is fixing that. We're building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved. We're expanding our forward-deployed engineering team in Chicago, a major hub for our customers and the heart of U.S. freight operations. In this role, you'll be embedded directly into the environments where our product meets real users. You'll work side-by-side with operators, understand their workflows firsthand, and turn that knowledge into robust integrations and production features. As our first Forward-deployed engineer at FleetWorks, you'll own outcomes end-to-end: diagnosing messy real-world problems, shaping technical solutions in the field, and ensuring our AI agents perform flawlessly in live operations. If you thrive in ambiguous environments, enjoy working directly with customers, and want to see your code deliver immediate operational impact, this role is uniquely high-leverage. Learn about our Series A here! https://www.fleetworks.ai/blog/fleetworks-launches-always-on-dispatcher-for-trucking-industry-with-17m-funding WHAT YOU'LL DO: - Own customer deployments end-to-end, from initial scoping to integration design to production rollout. - Work directly with customer operators and leaders to understand real workflows, pain points, and edge cases, translating them into clear, high-quality technical solutions. - Build production features and

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