Why project44?

At project44, we believe in better.

We challenge the status quo because we know a better supply chain isn’t just possible—it’s essential. Better for our customers. Better for their business. Better for the world.

With our Decision Intelligence Platform, Movement, we’re redefining how global supply chains operate. By transforming fragmented logistics data into real-time, AI-powered insights, we empower companies to connect instantly, see clearly, act decisively, and automate intelligently. Our Supply Chain AI enhances visibility, drives smarter execution, and unlocks next-gen applications that keep businesses moving forward.

Headquartered in Chicago, IL with a 2nd HQ in Bengaluru, India we are powered by a diverse global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose.

AI at project44

We expect every project44 team member, regardless of role or function, to actively leverage AI in their day-to-day work. Whether you're building product, serving customers, managing people, or running operations, AI is a tool you're expected to use with intent, curiosity, and judgment. We don't expect everyone to be a data scientist. We do expect everyone to be an intelligent user of AI: able to identify where it adds value, direct it effectively, evaluate outputs critically, and govern it responsibly. We invest in our team's AI fluency because we believe it's a competitive advantage for every person at project44, not just our engineers.

If you’re driven to solve meaningful problems, leverage AI to scale rapidly, drive impact daily, and be part of a high-performance team – we should talk.

Overview

The Prompt Engineer is a specialist in building, expanding, and managing AI Agents that power project44’s AIA Operations organisation. Acting as both an AI workflow architect and operational strategist, the Prompt Engineer plays a central role in designing, governing, and scaling the operational frameworks that underpin AIA Operations globally.

What you’ll own

This role partners closely with global Product, Engineering, AI, and Operations leaders to shape AI Agents’ long-term performance trajectory, define engineering standards, and embed best practices that strengthen consistency and scalability across regions. The Prompt Engineer operates as an individual contributor — driving measurable operational improvement through deep domain expertise, disciplined experimentation, and cross-functional collaboration.

AI Workflow Development & Prompt Engineering

• Design, build, and maintain AI agent workflows that automate carrier monitoring, performance tracking, exception management, and escalation processes.
• Build custom, customer-specific AI agent workflows tailored to individual carrier, lane, or account requirements, adapting core workflow patterns to unique operational needs.
• Write, test, iterate, and optimise prompts for large language models, ensuring accuracy, reliability, and operational efficiency.
• Run structured tests to evaluate prompt performance, comparing variants against defined criteria and documenting what works, what doesn’t, and why.
• Track prompt versions and iterations, maintaining clear records of changes, evaluation outcomes, and the reasoning behind design decisions.
• Identify where LLM outputs fall short of operational requirements and systematically diagnose and resolve issues through prompt refinement.
• Work closely with engineers through the handover and deployment process, ensuring workflows are correctly implemented and behave as intended at go-live.
• Ramp up new use cases post-launch — gradually expanding scope and coverage, surfacing edge cases as real-world volume increases, and refining prompts accordingly.
• Monitor agent performance on an ongoing basis, identifying drift, degradation, or failure modes and re-iterating on prompts to maintain accuracy and reliability over time.
• Maintain and support existing production workflows throughout their lifecycle, applying fixes, updates, and enhancements as customer needs, data sources, or underlying models evolve.
• Evaluate new AI tools and platforms, providing structured recommendations on adoption and integration into existing team workflows.

Operational Governance

• Continuously increase AI Agent build velocity by escalating process pain points and driving improvements.
• Identify opportunities to expand automation coverage and proactively bring forward structured proposals for new AI capabilities.
• Support continuous improvement across the full AI Agent build lifecycle, including process optimisation and efficiency gains.

Cross-Functional Collaboration

• Read and interpret Product Requirements Documents (PRDs), transforming them into clear AI agent requirements that define what the workflow needs to do, how success will be measured, and what constraints apply.
• Work with Product Managers throughout the full agent build lifecycle — from initial requirements through to go-live — ensuring the agent is built to expectations and flagging any gaps or ambiguities early.
• Work closely with engineers who build the connectors that deploy AI agents, ensuring clear handover of prompt designs and workflow logic, and collaborating through go-live to resolve any issues.
• Collaborate with external vendors to reduce friction and influence new feature releases.

Customer Collaboration

• Partner directly with customers to understand their operational goals and translate them into tailored AI agent workflows and clear success criteria.
• Work directly with customers post-launch to review agent performance, gather feedback, and drive iterative improvements that increase accuracy and value delivered.
• Serve as a subject-matter point of contact for customers on agent behaviour, troubleshooting, and enhancement requests, balancing customer needs with engineering feasibility.

Team Enablement

• Contribute to training resources, internal knowledge bases, and team documentation that raise the AI capability of the broader function.
• Champion a culture of disciplined experimentation, continuous learning, and rigorous quality standards across the team.

Experience

• 3-4+ years in transportation operations, logistics technology, carrier management, or network operations; global or multi-region experience preferred.
• Hands-on experience working with AI tools, automation platforms, or workflow-based technologies in an operational context.
• Troubleshooting experience across EDI, API, data pipelines, system configuration, and workflow orchestration.
• Strong analytical skills — comfortable using data, monitoring dashboards, and structured observation to diagnose problems and measure outcomes.
• Demonstrated ability to work collaboratively across Product, Engineering, AI, and Operations stakeholders.
• Excellent written and verbal communication skills; able to read and interpret product requirements and translate them into clear, structured specifications for AI workflows.

Prompt Engineering & AI Skills

• A genuine curiosity about how LLMs work and a methodical approach to testing and refining prompts — patience and rigour matter more than prior formal training.
• Ability to write clear, structured prompts and instructions that direct AI behaviour accurately and consistently.
• Familiarity with core prompting techniques such as step-by-step instructions, examples within prompts (few-shot), and breaking complex tasks into stages.
• Comfort working in AI tools and platforms to build, test, and iterate on workflows without needing to write code.
• Ability to critically evaluate LLM outputs — spotting errors, inconsistencies, and failure modes — and translate observations into targeted prompt improvements.
• An understanding of LLM behaviour and limitations — including how models can hallucinate, misinterpret instructions, or produce inconsistent outputs — and how to design prompts that account for these tendencies.

Success Profile

• Scaled, productionised AI workflows that drive measurable improvements in automation coverage, accuracy, and operational efficiency.
• Accelerated resolution of complex, high-impact incidents through expert diagnostics and systemic remediation.
• Effective cross-regional governance and operational standardisation that enhances global team maturity.
• Recognised expertise that strengthens organisational capability and advances AIA Operations’ AI transformation roadmap.

Work from office expectations: This role requires you to operate from office all 5 days in a week. 

Diversity & Inclusion

At project44, we're designing the future of how the world moves and is connected through trade and global supply chains. As we work to deliver a truly world-class product and experience, we are also intentionally building teams that reflect the unique communities we serve. We’re focused on creating a company where all team members can bring their authentic selves to work every day.

We’re building a company that every one of us at project44 is proud to work for, and our journey of becoming a more diverse, equitable and inclusive organization, where all have a sense of belonging, is shaped through the actions of our leadership, global teams and individual team members. We are resolute in our belief that each team member has an equal responsibility to mold and uphold our culture.

project44 is an equal opportunity employer seeking to enrich our work environment by creating opportunities for individuals of all backgrounds and experiences to thrive. If you share our values and our passion for helping the way the world moves, we’d love to review your application!

For any needed accommodations during the hiring process, please email [email protected]. Even if you don’t meet 100% of the above job description you should still seriously consider applying. Studies show that you can still be considered for a role if you meet just 50% of the role’s requirements.

More about project44

Since 2014, project44 has been transforming the way one of the largest, most important global industries does business. As transportation and logistics continue to evolve and customer expectations around delivery become more demanding, industry technology must rise to the occasion. In just a few short years, we have created a digital infrastructure that eliminates the inefficiencies caused by dated technology and manual processes. Our Advanced Visibility Platform is used by the world’s leading brands to track shipments, collaborate with supply chain partners, drive operational efficiencies, and create outstanding customer experiences.