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Flexport

Staff Software Engineer, Autonomous Freight Systems

Flexport · San Francisco, California, United States

Posted about 3 months ago

or apply directly on Flexport's site. We never take the application ourselves.

Is this posting real?

This role has been open
82 days
Flexport's roles stay open a median of 82 days
Reposted
No
Salary listed
No
3% of Flexport's roles list one
Ghost-job risk at Flexport
high
175 stale, 3 reposted of 176 open
Hiring momentum
234 roles opened in the last 90 days
↑ up vs. the prior 90 days
Last confirmed on the employer's board
2026-10-24

Measured from postings appearing on and disappearing from Flexport's own greenhouse board since 2026-08-03. Full hiring picture for Flexport.

About this role

As a Staff Software Engineer on the Autonomous Freight Systems team at Flexport, you will lead the development of an AI-powered rates platform and self-serve freight booking experience. Your role involves designing AI agents for pricing intelligence and booking compliance, creating secure AI infrastructure, and mentoring other engineers. You will work closely with various teams to tackle complex logistics challenges and contribute to a tech-driven sales model.

Our read on this posting2.6out of 5
benefits
2/5
freshness
1/5
career value
5/5
role clarity
5/5
pay transparency
0/5

Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Flexport as an employer.

What you need

  • LLM Fluency: Experience with agent patterns, RAG, and prompt engineering.
  • Agentic Orchestration: Experience with workflow orchestration (e.g., Temporal) and building reliable systems around non-deterministic AI.
  • Entrepreneurial Drive: Ability to identify high-leverage automation problems and design AI-driven solutions.
  • Product Instincts: Proven track record of building data-heavy applications with a focus on user interaction.
  • Architecture Leadership: Experience leading technical initiatives across multiple teams or systems, specifically in building unified interfaces.
  • Technical Rigor: Experience with simple, well-tested code and large-scale distributed systems.

Nice to have

  • Experience with Java, Spring Boot, Ruby on Rails, React, AWS.
  • Experience in logistics, supply chain, or freight technology.
  • Experience building internal tools or operator-facing applications.
  • A bias for action: Proactive problem-solving.

What you get

  • Base salary range of $196,875 — $270,703 USD.
  • Bonus and equity opportunities.
  • Comprehensive benefits including medical and dental.
  • Flexible time off.

Worth weighing

  • The role involves working with cutting-edge AI technologies, but may require navigating complex and evolving challenges without established solutions.
  • The position is described as a ground-floor opportunity, which may imply a high level of responsibility and ambiguity in initial phases.
  • No specific mention of remote work; the role is listed as onsite.

Summarised from Flexport's posting. Read the full original.

Listed by Flexport on their greenhouse job board, last confirmed open on 2026-10-24. PitchMeAI is not the employer.

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