Principal Software Engineer

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.      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.

We are looking for a Principal Software Engineer to join the project44 Engineering Team in Chicago ! You will work in a fast-paced Agile team to design and implement Java applications.

Key Responsibilities & Accountabilities

Technical Leadership

Drive large-scale, cross-organizational engineering initiatives from concept through delivery.

Define and evolve  long-term architecture to ensure scalability, reliability, and security.

Serve as a technical authority , making high-impact design and technology decisions.

Influence & Collaboration

Partner with product, design, and leadership to align technical vision with business priorities.

Balance short-term deliverables with long-term platform health and architectural integrity.

Communicate trade-offs clearly and build consensus across diverse stakeholders.

Engineering Excellence

Set and uphold high standards for code quality, design, testing, and operational maturity.

Lead design reviews, architecture deep dives, and technical mentorship for senior engineers.

Foster a culture of craftsmanship, continuous improvement, and innovation.

Systems Thinking

Identify systemic inefficiencies and propose strategic reforms to improve developer velocity and reliability.

Anticipate scaling challenges, technical debt, and organizational blind spots.

Shape roadmaps that balance feature delivery with technical leverage.

Pragmatism & Impact

Lead with clarity and practicality , focusing on measurable outcomes and sustainable engineering.

Know when to optimize, when to move fast, and when to challenge assumptions.

Ensure decisions are grounded in data, experience, and real-world trade-offs.

Culture & Mentorship

Model ownership, curiosity, and accountability.

Mentor engineers and inspire them to push boundaries in both technology and teamwork.

Act as a cultural multiplier , promoting innovation, empathy, and continuous learning.

Requirements :

10+ years of software engineering experience, with deep expertise in Java and / or Python.

Proven success designing and scaling distributed systems serving large user bases or high throughput.

Experience influencing architecture and strategy across multiple teams (60+ engineers).

Strong communication and stakeholder management skills.

A track record of technical innovation and measurable business impact.

What Success Looks Like

Clear, scalable, and resilient technical architecture aligned with business growth.

Improved developer experience, velocity, and operational stability.

Teams that deliver high-quality software confidently and consistently.

A culture of technical excellence and continuous improvement, led by example.

In-office Commitment :   Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed to joining our team on-site,  in our beautiful headquarters four days a week . Together, we’re building something extraordinary—learn, grow, and thrive in our fast-paced, transformative environment.

Diversity & Inclusion

We’re designing the future of how the world moves and is connected through trade and global supply chains. We can only deliver a truly world-class product and experience if our teams are as diverse and unique as the communities we are building for. It’s up to us to create a company where anyone can bring their authentic self to work every day. We’re constantly working to improve, and we accept our responsibility to elevate the voices left in the margins. It’s on every one of us.

Our focus on inclusion manifests in the way we hire, the customers we serve, and the regions we prioritize. We’re building a company that every one of us at project44 is proud to work for : a company that celebrates you for being you.

We pride ourselves on celebrating everyone — project44 is an equal opportunity employer actively working on creating a diverse and inclusive work environment where underrepresented groups can 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 accommodations needed during the hiring process, please email recruiting@project44.com. Even if you don’t meet 100% of the above qualifications, 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.