Director, Technology

Roadrunner Transportation Services•Downers Grove, IL

8h•$140,000 - $160,000•Hybrid

About The Position

Roadrunner is one of the fastest-growing LTL (Less-Than-Truckload) carriers in the country — and we're building the technology to match. We're not your typical freight company. We move fast, think big, and believe that great software is a genuine competitive weapon in logistics. We're looking for a Director of Technology who gets that. Someone who has shipped products that moved the needle for a business, who knows what it takes to go from whiteboard to production, and who can inspire a team to do their best work. If you've spent your career building software that matters — and you want to do that at scale in one of the most operationally complex industries in the world — read on. Roadrunner’s Smart Long Haul is revolutionizing the industry with significant investments in technology, a culture of continuous improvement, and intelligent and efficient direct routing. A Top 100 Trucking company by Inbound Logistics and a Top Tier Service Carrier by Mastio, Roadrunner is an LTL industry leader on the rise. As a long-haul, metro-to-metro LTL carrier, Roadrunner offers more direct routes than any other nationwide Less-than-Truckload carrier in the United States. With a nationwide presence, terminals across 40+ markets, and more than $400 million in revenue, the company’s Smart Long-Haul Network is the preferred choice for shippers looking to move freight quickly and reliably. Roadrunner is growing and looking for a highly motivated Director of Technology to join our winning team. If you are results driven and looking for a rapidly growing company with high growth and earnings potential, apply today! We Run Safe. We Run Smart. We Run Together.

Requirements

7+ years in technology leadership.
A genuine track record of delivering software products that created measurable business value where you can point to specific outcomes, not just delivery activity.
Deep experience leading cross-functional software delivery teams through the full product lifecycle, from discovery to production to iteration.
Strong business acumen. You understand return on investment and and how technology investment connects to business outcomes.
Excellent communicator who can speak fluently to both engineers and executives and knows when each audience needs more or less detail.
Experience hiring, developing, and retaining strong engineering talent in competitive markets.
Hands-on enough to ask the right technical questions and earn the respect of engineers, without needing to be in the weeds day-to-day.

Nice To Haves

Experience in transportation, logistics, supply chain, or other operationally complex industries.
Background in management consulting or strategy consulting, with experience driving technology-enabled business transformation.
Familiarity with Azure and the architectural patterns that make software scalable and resilient.
Experience with data-intensive products, real-time tracking, route optimization, dynamic pricing, or similar domains.
Startup or scale-up experience where you've had to build with limited resources and make high-impact decisions under uncertainty.

Responsibilities

Ship Software That Creates Real Business Value Own the end-to-end delivery of technology products across Roadrunner's core operational domains — freight management, pricing, customer experience, driver tools, and network optimization.
Partner closely with business stakeholders to deeply understand the problems we're solving, then cut through ambiguity to define what we build, in what order, and why it matters.
Drive a delivery culture where teams ship frequently, learn fast, and continuously improve — not one bogged down in process theater or endlessly deferred launches.
Define and track meaningful delivery metrics (cycle time, deployment frequency, change failure rate, time-to-value) and use them to make smarter decisions and demonstrate impact.
Build and own the technology delivery roadmap — balancing new product development, platform investment, and technical debt reduction against business priorities.
Ensure every significant technology initiative has a clear business case, measurable outcomes, and an accountable owner from kickoff through post-launch learning.
Lead and Grow the Engineering Team Recruit, develop, and retain a high-caliber team of software engineers, tech leads, and delivery managers who are motivated by ownership and real impact.
Create an environment where engineers are close to the business problems they're solving — not just order-takers executing tickets handed down from above.
Coach and develop engineering managers and tech leads, building the next layer of technical leadership within the organization.
Champion engineering practices that improve quality and velocity: automated testing, thoughtful code review, observability, and continuous deployment.
Bridge Technology and the Business Be a trusted partner to Operations, Sales, Pricing, and Customer Experience by translating business needs into technology solutions that are practical, scalable, and delivered on time.
Communicate clearly and credibly with executive leadership about technology strategy, delivery status, risk, and investment tradeoffs.
Proactively surface delivery risks, architectural concerns, and capacity constraints before they become problems and propose paths forward, not just a status update.
Represent technology in cross-functional planning, ensuring Technology has a seat at the table when business strategy is being shaped.
Raise the Bar on How We Build Assess and evolve Roadrunner's engineering practices, tooling, and architecture to support faster, higher-quality delivery as the team and product complexity scales.
Drive the adoption of modern software delivery practices including, continuous integration, and feature flagging for safe, incremental releases.
Establish lightweight but effective engineering standards — from code quality to incident response — that create consistency without stifling autonomy.
Identify and address systemic sources of slowness or fragility in the delivery pipeline, whether they're technical, organizational, or process-related.
Stay current on emerging tools, platforms, and industry trends, and bring well-reasoned perspectives on where Roadrunner should invest and where we should hold off.