We are looking for the Best of the Best. Action driven leaders who want to be part of real change and help design the future of LTL in the U.S. This is a place where high performers can grow, influence outcomes, and make an impact while working directly with executives and smart people from across industries.
We bring a winner mindset. We take ownership, raise the bar, and measure ourselves by results. We Run Safe. We Run Smart. We Run Together. These principles create an environment of high standards, clear ownership, and direct collaboration. We trust data over intuition, move with urgency, and hold each other accountable because winning requires it.
Roadrunner exists to prove that LTL can be better than the industry has settled for. To be the best means we need to think bigger, look outside the box, and question every assumption: too many handoffs, limited visibility, and the quiet belief that “this is just how it works.” We rejected that story. We built a proprietary Smart Network™ for direct, long haul, metro to metro service that delivers fewer touches, faster transit, real time visibility, and genuine accountability. We are the most tech forward company in LTL, and we are not finished widening the gap.
The foundation is already strong. Recognized as one of Built In Chicago’s Best Large Places to Work. Earning top marks for improvement, quality, and service. The real opportunity is still ahead: helping invent what comes next.
If you want to be evaluated among the Best of the Best and help set the new standard in LTL, we should talk.What you’ll do1. Lead Infrastructure Strategy and Technology Modernization
- Develop and execute infrastructure, cloud, and security strategies aligned with business objectives.
- Create and maintain technology roadmaps that support scalability, performance, and operational resilience.
- Evaluate emerging technologies and recommend solutions that improve business outcomes.
- Partner with senior leadership to align infrastructure priorities with organizational goals.
- Drive continuous modernization initiatives across enterprise systems and platforms.
- Lead the management of enterprise infrastructure including servers, virtualization, storage, networking, backup, and disaster recovery solutions.
- Ensure infrastructure environments deliver high availability, reliability, and performance.
- Establish operational standards, governance frameworks, and service delivery expectations.
- Monitor infrastructure health and proactively address risks, capacity needs, and performance concerns.
- Drive operational excellence through measurable service improvements and accountability.
- Lead cloud strategy, architecture, and operational management across enterprise environments.
- Guide cloud migration, optimization, and modernization initiatives.
- Implement scalable cloud operating models focused on security, efficiency, and cost management.
- Establish best practices for cloud governance, performance monitoring, and resource management.
- Ensure cloud platforms support current business requirements and future growth objectives.
- Partner with internal stakeholders to enhance organizational security posture.
- Oversee infrastructure security controls, identity management, access governance, and system hardening initiatives.
- Support incident response planning, execution, and post-incident review processes.
- Drive remediation efforts and risk mitigation strategies across infrastructure domains.
- Ensure compliance with organizational security policies, standards, and regulatory requirements.
- Lead, develop, and mentor Infrastructure, Cloud Engineering, and Security teams.
- Create an environment focused on collaboration, accountability, continuous learning, and execution excellence.
- Recruit and retain top technical talent while building leadership capability within the organization.
- Establish clear goals, performance expectations, and career development pathways.
- Foster a culture that embraces innovation, ownership, and operational discipline.
- Partner with business leaders to understand operational priorities and technology needs.
- Translate business requirements into scalable technology solutions and strategic initiatives.
- Manage vendor relationships, technology partnerships, and infrastructure-related budgets.
- Develop metrics and reporting frameworks that provide visibility into performance, risk, and service quality.
- Ensure infrastructure investments deliver measurable business value.
Required Qualifications
- Bachelor’s degree in Information Technology, Computer Science, Engineering, or a related discipline; equivalent professional experience will be considered.
- 8+ years of progressive experience in IT infrastructure, cloud engineering, or technology operations.
- 3+ years of leadership experience managing technical teams and enterprise technology environments.
- Proven experience developing and executing infrastructure strategies in complex business environments.
- Demonstrated success managing enterprise infrastructure operations, cloud platforms, and security initiatives.
Technical Expertise
- Strong knowledge of enterprise infrastructure including servers, virtualization, storage, backup, disaster recovery, and networking technologies.
- Experience with public cloud platforms and cloud modernization initiatives.
- Knowledge of cybersecurity principles, identity and access management, infrastructure security, and incident response.
- Experience implementing operational processes, performance monitoring, and technology governance frameworks.
- Ability to evaluate technology investments and align solutions with business outcomes.
Leadership & Business Acumen
- Experience managing vendors, contracts, budgets, and strategic technology initiatives.
- Strong communication and stakeholder management skills across technical and non-technical audiences.
- Proven ability to lead cross-functional initiatives and influence organizational decision-making.
- Demonstrated success building, mentoring, and developing high-performing technical teams.
Preferred Qualifications
- Experience leading cloud transformation or infrastructure modernization programs.
- Industry certifications related to cloud platforms, infrastructure, cybersecurity, or technology leadership.
- Experience supporting multi-site or enterprise-scale technology environments.
- Strong understanding of business continuity, disaster recovery, and operational resiliency planning.
- You think in systems, not tasks.
- You balance long-term strategy with operational execution.
- You own outcomes, not activity.
- You make decisions using data, risk assessment, and business impact.
- You build trust through transparency, accountability, and follow-through.
- You challenge legacy processes and drive continuous improvement.
- You move with urgency without sacrificing quality, security, or stability.
- You develop people as intentionally as you develop technology.
- You communicate clearly with executives, peers, and technical teams.
- You thrive in environments where performance, reliability, and innovation matter.
We’re not just moving freight; we’re reimagining long-haul shipping. Our Smart Network™ offers more direct long-haul metro-to-metro routes than any other nationwide LTL carrier in the United States, with service extending into Canada and Mexico and terminals across 40+ metro markets. Powered by AI and machine learning, our operations platform ensures real-time tracking, custodial control, and full shipment visibility. With driver teams executing over-the-road (OTR) moves — and no freight moving on rail — customers experience industry-leading transit times, minimal rehandling, and dramatically reduced risk of loss or damage.
Our 900+ owner-operators benefit from scheduled freight, fewer touches by design, consistent long-haul density, and a differentiated metro-to-metro model that creates predictable earning opportunities.
This precision and performance have earned Roadrunner national recognition by over 3,000 shippers, and was ranked this year #1 in Operations, #1 in Technology, and #1 in Value in the Quest for Quality Awards, as well as honors as a Top 100 Trucking Company by Inbound Logistics and a Top Tier Service Carrier by Mastio.
We’re growing fast. Roadrunner is building something special with great people, a winning culture and a differentiated service offering in the marketplace. Join us today to grow your career!
We Run Safe. We Run Smart. We Run Together.
Compensation & Setup- Pay: $140,000 annual base salary
- Location: Onsite - Downers Grove, IL
- Benefits: Full benefits package including medical, dental, vision, retirement savings plan, paid time off, and other company-sponsored benefits
The physical demands and work environment described here are representative of those an employee encounters while performing the essential functions of this position. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions.
Physical Demands- Sedentary physical activity performing non- strenuous daily activities of an administrative nature.
- While performing the duties of the job, the employee is regularly required to sit, walk, stand, reach/handle items, work with the fingers, and talk and hear others in conversations via the phone or in person.
- The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job.
- The noise level in the work environment is usually moderate.
* The above statements reflect the general details necessary to describe the principal functions of the position and are not intended to be all inclusive. The position and any of the requirements listed above are subject to change at any time according to the changing needs of the company.
* Roadrunner is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind.
* We will not accept unsolicited candidates from external recruiters or recruiting agencies. Thank you!
#LI-OnsiteDowners Grove, IL
Skills Required
- Bachelor's degree in IT, Computer Science, Engineering or related field (or equivalent experience)
- 8+ years progressive experience in IT infrastructure, cloud engineering, or technology operations
- 3+ years leadership experience managing technical teams and enterprise technology environments
- Proven experience developing and executing infrastructure strategies in complex business environments
- Demonstrated success managing enterprise infrastructure operations, cloud platforms, and security initiatives
- Strong knowledge of enterprise infrastructure: servers, virtualization, storage, backup, disaster recovery, and networking technologies
- Experience with public cloud platforms and cloud modernization initiatives
- Knowledge of cybersecurity principles, identity and access management, infrastructure security, and incident response
- Experience implementing operational processes, performance monitoring, and technology governance frameworks
- Experience managing vendors, contracts, budgets, and strategic technology initiatives
- Strong communication and stakeholder management skills across technical and non-technical audiences
- Proven ability to lead cross-functional initiatives and influence organizational decision-making
- Demonstrated success building, mentoring, and developing high-performing technical teams
- Experience leading cloud transformation or infrastructure modernization programs
- Industry certifications related to cloud platforms, infrastructure, cybersecurity, or technology leadership
- Experience supporting multi-site or enterprise-scale technology environments
- Understanding of business continuity, disaster recovery, and operational resiliency planning
What We Do
Roadrunner is the Smart Choice for long-haul, metro-to-metro LTL service throughout the country. With terminals across 40+ markets and a nationwide presence, Roadrunner’s Smart Network is the best option for shippers looking to move freight quickly and reliably. The company provides high-quality, scalable LTL freight services to shippers of all sizes across various industries. Roadrunner’s Smart Long Haul is revolutionizing the Less-than-Truckload industry with investments in technology, a culture of continuous improvement, and intelligent and efficient direct routing. Every day, the team at Roadrunner challenges itself to be more innovative and creative than the day before by setting high expectations and solving problems before they even happen. Our award-winning culture gives people the autonomy to build innovative solutions while taking a data-driven approach to become the Smart Choice for LTL shippers. At Roadrunner, we run safe, we run smart, and we run together.
Why Work With Us
WE RUN SAFE -We learn, train, and share safety best practices. WE RUN SMART -We use technology to optimize our operations. -We create opportunities for ourselves, our teammates, our customers, and our business. WE RUN TOGETHER -We celebrate each other's accomplishments. -We acknowledge our wins but are not afraid to fail. We are partners.
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