Lead Enterprise Application Engineer

Roadrunner’s enterprise applications connect the systems, teams, and third-party platforms that power the business. As the application environment grows in scale and complexity, disciplined ownership is critical to maintaining reliability, strengthening integrations, and ensuring technology investments deliver measurable operational value.

The Lead Enterprise Application Engineer owns the performance and evolution of key vendor applications across their full lifecycle. This role serves as the senior escalation point for complex application issues, leads implementations from requirements through stabilization, and aligns business needs with secure, scalable technical solutions.

Success means building an application function that operates with greater visibility, stronger controls, faster issue resolution, and clear accountability. It also means improving how Roadrunner evaluates vendors, manages application roadmaps, executes technical initiatives, and develops future engineering leadership.



What you’ll do

1. Own enterprise application reliability

• Serve as the final internal escalation point for complex third-party application issues, driving incidents through root-cause analysis and resolution.
• Coordinate development, infrastructure, network, security, and vendor teams to resolve issues that cross systems or technical domains.
• Establish and improve service-level expectations, escalation paths, support runbooks, and operating procedures for assigned applications.
• Monitor application health, recurring incidents, vendor performance, and operational risk to identify opportunities for proactive improvement.
• Maintain strong access controls and support regular audits to ensure applications operate in alignment with security requirements.

2. Lead software implementations and technical initiatives

• Lead vendor application implementations and major upgrades from requirements and solution design through configuration, integration, testing, cutover, and hypercare.
• Own project scope, timelines, dependencies, resources, risks, and stakeholder communication for assigned technical initiatives.
• Translate business requirements into practical technical options, including recommendations on when to configure, integrate, automate, or build.
• Define clear success criteria and ensure delivered solutions meet business, operational, security, and supportability requirements.
• Drive implementation decisions with urgency while maintaining appropriate technical discipline and change control.

3. Strengthen integrations and technical architecture

• Partner with development teams to deliver reliable APIs, EDI connections, data feeds, and other system integrations.
• Assess how proposed solutions fit within Roadrunner’s broader application, infrastructure, data, and security ecosystem.
• Establish documentation and support standards that improve integration reliability, troubleshooting, and long-term maintainability.
• Identify technical dependencies and risks early, then coordinate the right teams to address them before they affect delivery.
• Use SQL, scripting, application logs, and integration tools to investigate issues and improve operational visibility.

4. Drive product ownership and vendor performance

• Act as product owner for assigned vendor platforms, maintaining the roadmap, backlog, priorities, and release plans.
• Partner with business stakeholders to evaluate demand, clarify tradeoffs, and prioritize work based on operational value and risk.
• Manage day-to-day vendor relationships, including service performance, SLAs, release management, renewals input, and issue escalation.
• Evaluate vendor solutions for functional fit, technical compatibility, security risk, total cost, and long-term scalability.
• Hold vendors accountable for commitments while maintaining productive relationships focused on business outcomes.

5. Build a scalable application engineering function

• Lead, mentor, and develop a junior application engineer through clear expectations, technical guidance, and consistent accountability.
• Establish standards for documentation, knowledge management, change control, and operational execution.
• Partner with subject matter experts to improve user guides, training materials, system documentation, and knowledge base content.
• Identify opportunities to automate repetitive support and operational work, including responsible uses of AI-enabled tools.
• Take on broader technical and people leadership responsibilities as the application engineering function evolves.

What you bring

• Bachelor’s degree in Computer Science, Engineering, or a related field, or equivalent professional IT experience.
• 6+ years of experience in application support, systems administration, application engineering, or a related technical discipline.
• Advanced experience providing Tier 3 application support and resolving complex issues across integrated systems.
• A demonstrated record of leading software implementations, major upgrades, or technical initiatives from planning through production stabilization.
• Experience working directly with business users to gather requirements, evaluate options, and translate needs into technical solutions.
• Experience managing third-party technology vendors, service expectations, escalations, and delivery commitments.
• Strong understanding of application integrations, APIs, EDI, data feeds, SQL, scripting, and software engineering principles.
• Experience coordinating work across development, infrastructure, networking, security, and business teams.
• Leadership or mentoring experience, with the ability to set standards and develop technical talent.
• Strong project management, problem-solving, communication, and stakeholder management capabilities.
• Ability to work independently, make sound decisions, and drive results in a fast-moving environment.

Preferred qualifications:

• Experience in logistics, transportation, trucking, or another operationally complex industry.
• Product owner experience, including roadmap development, backlog management, and stakeholder prioritization.
• Experience leading engineers or preparing for formal people-management responsibilities.
• Experience managing cross-functional technical projects with multiple dependencies.
• Experience applying AI, workflow automation, or support automation tools to improve operational performance.

How you operate

• You think in systems, not isolated tasks.
• You own outcomes from initial problem definition through sustained production performance.
• You bring structure to complex work without slowing execution.
• You investigate root causes rather than repeatedly treating symptoms.
• You challenge assumptions constructively and make recommendations grounded in business value, risk, and technical reality.
• You move quickly without creating operational chaos or unnecessary technical debt.
• You communicate clearly, directly, and decisively with technical and nontechnical stakeholders.
• You understand when to solve an issue independently and when to mobilize the broader organization.
• You document decisions and create processes that make the team stronger after the immediate work is complete.
• You hold yourself, internal partners, and vendors accountable for commitments.




Compensation & Setup

• Compensation: $110,000 annual base salary
• Location: Hybrid | Downers Grove, IL
• Benefits: Competitive benefits package including medical, dental, and vision insurance, 401(k), paid time off, and growth opportunities

Physical Demands and Work Environment

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 and handle items, work with the fingers, and talk and hear others in conversations by phone or in person.

Work Environment

• The noise level in the work environment is usually moderate.
• Regular onsite presence is required based on the team’s hybrid work schedule and business needs.

* 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-HybridDowners Grove, IL




About Roadrunner

Roadrunner is for ambitious, smart people who excel at execution over talking about it, and who would rather invent the next standard in freight than accept the status quo.

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.