Director of Support and Observability

RaceTrac Company Overview

Job Description:

We seek an experienced, visionary, hands-on leader to ensure the best possible Guest experiences. It achieves this by proactively monitoring the user experience and underlying technology health and proactively addressing issues before they impact the Guest. As a strategic thought leader, you will define and implement the systems observability and Levels 1 & 2 strategy, tools, processes, and people resources.

This is an execution-focused role with 24x7x365 responsibility for the observability platform and support operations, requiring the management of incidents, proactive problem-solving, and leadership in continuous improvement. You will design and implement a comprehensive framework across on-premises and Azure Cloud environments, ensuring proactive monitoring and alerting processes while transforming reactive Operations and Level 1 & 2 support teams into highly efficient, proactive units. You will oversee the team but have direct engagement at the operational level, including delivery and support, including on-call and escalations as needed. You will be the voice to the business and technology stakeholders on systems and Guest experience health.

Responsibilities:

• Promotes and maintains a culture where Stability is a product.
• Collaborates with the business partners, digital peers, IT security, enterprise architecture and Store System teams to produce thorough visibility of guest transactions through both digital platforms and in-store digital integrations.
• Produces and manages strategy for incident response and resolution for end-to-end digital transactions.
• Owns digital monitoring solutions and end-to-end architecture of digital monitoring that ensure visibility and remediation of digital guest transactions.
• Manages 3rd party vendor relationships responsible for end-to-end monitoring and support.
• Establishes and manages relationships with internal stakeholders and senior leadership throughout the company to communicate and guarantee the delivery of a high-quality product.
• Discovers new opportunities to optimize the business through improved processes and functional enhancements.
• Owns and influences adherence to strategy that ensures support organization can effectively triage and remediate.
• Develops and refines metrics that expose digital and store health.
• Directly manages IT professionals and ensures growth and career development opportunities are provided; serves as an expert in the Information Systems field and provides leadership and direction to team on industry best practices.
• Maintain and manage the vision for a predictable release plan for digital product that adheres to RaceTrac’s agile approach to software development.
• Leads cross-functional team of engineers and advocates on their behalf, removes roadblocks, and helps them navigate how to achieve goals while holding them accountable to project commitments and quality standards.
• Develops and maintains strategy and budget for Digital Support and Release activities.

Qualifications:

• 10 years of experience in observability, monitoring, infrastructure, or operations roles, with significant leadership experience.
• Proven track record of building and leading observability functions across hybrid environments (on-prem and cloud), particularly in Azure Cloud.
• Hands-on experience managing observability platforms, Levels 1 and 2 support teams, and operational outcomes, including incident management and after-hours escalations.
• Experience in transforming reactive support and operations teams into proactive units by integrating observability solutions.
• Strong experience in managing change and overcoming resistance in a complex, multi-team environment.
• Expertise in observability tools such as Splunk, Dynatrace, Azure Monitor, Log Analytics, and other hybrid monitoring solutions.
• Deep knowledge of cloud-native observability (especially Azure) and experience with on-prem infrastructures.
• Strong understanding of Site Reliability Engineering (SRE), DevOps, and ITIL frameworks, with experience in incident management, monitoring, and performance optimization.
• Exceptional ability to lead cross-functional teams and influence key stakeholders at all levels, from technical teams to executive leadership.
• Expert in product ownership, vendor management, and financial oversight, with experience building roadmaps, prioritizing improvements, and developing business cases.
• Proven success in fostering collaboration between development, operations, and support teams to deliver proactive monitoring and support capabilities.

All qualified applicants will receive consideration for employment with RaceTrac without regard to their race, national origin, religion, age, color, sex, sexual orientation, gender identity, disability, or protected veteran status, or any other characteristic protected by local, state, or federal laws, rules, or regulations.