Development ManagerFull-timeLead · 12+ yearsChicagoHybrid
microservices architectureagentic AI systemsdata scienceengineering leadership
project44 is hiring a Head of Engineering. You will define the technical direction for our AI agent-based logistics platform and build and lead high-performing engineering teams across the US and Europe. A deep understanding of microservices architecture and data science is essential, along with over 12 years of software development experience and 8+ years of leadership experience. This is a hybrid role requiring three days of on-site work per week at our Chicago headquarters.
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At project44, we believe in better — and p44LSP.ai is what better looks like for the logistics service provider market.
For years, project44 focused on global shippers as our core customer. That focus worked. Our Shipper business is a category leader growing 20% year-over-year. That strength is what makes the next chapter possible.
Shippers and LSPs are fundamentally different businesses. Shippers buy logistics software to support their core operations. Logistics Service Providers — freight forwarders, brokers, and 3PLs — sell logistics as their product. Their software is their competitive edge. They buy fast, build on APIs and agents, and reward teams that ship in weeks, not quarters.
This is why we created p44LSP.ai: a dedicated, AI-native division built to serve the LSP market with the focus, speed, and resources it deserves. It's the scope and ownership of an AI startup, backed by the infrastructure of a $124M business — 259K carriers, billions of shipment outcomes, agents in production, and direct access to project44's data graph, carrier network, and enterprise relationships.
This is a small, hand-picked team operating across Chicago, San Francisco, Bangalore, and the EU. Flat org. Forward-deployed engineering. AI coding tools across the workflow. Agents as the product surface. Customers who pilot in weeks and tell you what they think directly.
The LSP market is moving fast. AI agent startups are growing 300%+ year-over-year, and seven of eight sell to LSPs. We have the data position, the platform, the customers, and now the team. We're hiring the engineers who will build it with us.
The Role
This is not a caretaker role. You will set the technical direction for a division being built from the ground up, build the team, and own delivery against a product roadmap that moves fast. You ship, you lead, and you do both at the same time.
What You'll Own
Set and execute the technical vision — microservices architecture, agentic AI systems, data pipelines, and customer-facing product surfaces
Build and lead a high-performance engineering team across US and EU — hiring, developing, and retaining top talent
Own the agentic AI engineering roadmap — how agents are built, reasoned with, debugged, and improved in production
Partner with data science to design and build data-driven product capabilities that power LSP decision intelligence
Work closely with Forward Deployed Engineers to close the loop between customer reality and product roadmap
Represent engineering at the leadership level — contributing to product strategy, hiring, and go-to-market planning
Obsess over customers and ensure customers are successful in adopting LSP platform.
What We're Looking For
Qualifications
12+ years of software engineering experience with a strong track record of building and shipping large-scale products
8-10 years of engineering leadership — managing and growing high-performance teams
Hands-on experience with microservices architecture, agentic AI systems, and data science
Proven ability to design and build products end to end — from brief to production
Global team management experience is a strong plus
Logistics or supply chain technology experience is a strong plus
How You Lead
Hands-on without micromanaging — you know when to code and when to coach
You make decisions with incomplete information and own the outcomes
You attract strong engineers because strong engineers want to work for you
You operate with urgency without creating chaos
Some travel to Bangalore and to customers will be needed.
Work Authorization: Candidates must be authorised to work in the US without current or future employer-sponsored visa support.
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 3 days a week. Together, we’re building something extraordinary—learn, grow, and thrive in our fast-paced, transformative environment.
We continually evaluate our pay ranges to reflect skills, experience, and market conditions. The base salary offered will be determined by assessing a candidate's experience and skills relative to the scope and responsibilities of the position, as well as the specific geographic location where the job will be performed. Base salary is one component of project44's total compensation package, which also includes stock options for all EOR and project44-employed team members, bonus or commission eligibility depending on role, and a benefits package tailored to your country of employment. Specific benefits package offerings vary by country and may include health, dental, and vision coverage, retirement plans, and paid time off, in line with local market standards and statutory programs. The base salary range for this position is $235,000 – $290,000
Diversity & Inclusion
At project44, we're designing the future of how the world moves. As we work to deliver a truly world-class product, we're 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.
project44 is an equal opportunity employer. If you share our values and passion for the future of logistics, we'd love to review your application. Even if you don't meet 100% of the requirements, please consider applying — studies show you can still be a strong candidate at 50%.
