Head of Engineering (Chicago)

Why p44LSP.ai? 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 RoleThis 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 OwnSet and execute the technical vision — microservices architecture, agentic AI systems, data pipelines, and customer-facing product surfacesBuild and lead a high-performance engineering team across US and EU — hiring, developing, and retaining top talentOwn the agentic AI engineering roadmap — how agents are built, reasoned with, debugged, and improved in productionPartner with data science to design and build data-driven product capabilities that power LSP decision intelligenceWork closely with Forward Deployed Engineers to close the loop between customer reality and product roadmapRepresent engineering at the leadership level — contributing to product strategy, hiring, and go-to-market planningObsess over customers and ensure customers are successful in adopting LSP platform.What We're Looking ForQualifications12+ years of software engineering experience with a strong track record of building and shipping large-scale products8-10 years of engineering leadership — managing and growing high-performance teamsHands-on experience with microservices architecture, agentic AI systems, and data scienceProven ability to design and build products end to end — from brief to productionGlobal team management experience is a strong plusLogistics or supply chain technology experience is a strong plusHow You LeadHands-on without micromanaging — you know when to code and when to coachYou make decisions with incomplete information and own the outcomesYou attract strong engineers because strong engineers want to work for youYou operate with urgency without creating chaosSome 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.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%. For any accommodation needed during the hiring process, please email View email address on apply.placed-app.com.