Director, Technology

Job Description Summary

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.

• 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.

• 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.

• 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.

• 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.

• 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…