Sr Director, IT Application Operations

At Five Below our growth is a result of the people who embrace our purpose: We know life is way better when you are free to Let Go & Have Fun in an amazing experience, filled with unlimited possibilities, priced so low, you can always say yes to the newest, coolest stuff! Just ask any of our over 20,000 associates who work at Five Below and they'll tell you there's no other place like it. It all starts with our purpose and then, The Five Below Way, which is our values and behaviors that each and every associate believes in.

It's all about culture at Five Below, making this a place that can inspire you as much as you inspire us with big ideas, super energy, passion, and the ability to make the workplace a WOWplace!

We are seeking a Senior Director, Application Operations to lead the day-to-day operations and reliability of our enterprise-wide application ecosystem. With nearly 2,000 stores, $5B in annual revenue, and ~100 business-critical applications spanning Stores, Supply Chain, Finance, Digital, and HR, this role is central to ensuring stability, availability, and performance at scale.

Reporting directly to the CIO, this leader will own the Application Operations strategy, manage our Managed Service Provider (MSP) relationship, oversee a team of three internal Directors, and drive a culture of operational excellence, continuous improvement, and reliability engineering across the enterprise.

RESPONSIBILITIES

• Define and execute the Application Operations strategy, ensuring alignment with enterprise IT and business objectives.
• Lead, mentor, and develop a team of three internal Directors to form a high-performing Application Reliability and Operations function.
• Serve as the executive owner of the Managed Service Provider (MSP) contract for application operations.
• Ensure SLAs, OLAs, and KPIs are consistently met, driving vendor accountability through structured governance forums.
• Oversee the day-to-day health, stability, and performance of ~100 enterprise applications across Stores, Supply Chain, Finance, Digital, and HR.
• Lead and mature incident, problem, change, and release management processes, ensuring strong root cause analysis and preventive measures.
• Ensure that proposed and existing systems architectures are aligned with organizational goals and objectives.
• Act as the senior escalation point for critical business-impacting application issues.
• Partner with engineering and architecture teams to ensure operational readiness of new applications and releases.
• Drive the journey toward Site Reliability Engineering (SRE), focusing on automation, observability, proactive monitoring, and resilience.
• Manage vendor relationships, service level attainment, and drive all providers to high levels of quality delivery based on company requirements including RFPs, bid proposals, contracts, and scope of work.
• Ensure documentation of the company's existing services with vendors, partners, and internal team are up to date and maintained and make recommendations for improvements/alternatives and support long-term planning.
• Champion continuous improvement initiatives to reduce MTTD, MTTR, and recurring incidents.
• Leverage automation and AIOps to increase efficiency, predictive alerting, and self-healing capabilities.
• Ensure comprehensive documentation, runbooks, and knowledge management are current and accessible.
• Build strong business partnerships, ensuring high end-user satisfaction and alignment of services with business needs.
• Drive a data-driven, metrics-based culture, using operational dashboards and KPIs for continuous service improvement.
• Ensure compliance with regulatory, audit, and security standards (SOX, PCI, GDPR, CCPA).
• Partner with InfoSec to ensure timely patching, vulnerability management, and security compliance.
• Collaborate with procurement and finance to ensure cost optimization and value realization from the MSP contract.

QUALIFICATIONS

• University degree in the field of computer science or information systems
• 15+ years of progressive IT leadership experience, with at least 7+ years in application operations, service delivery, or reliability engineering.
• Service management certifications are desired.
• Proven track record managing large-scale enterprise applications across diverse business functions.
• Experience establishing a 12-18-month strategy and ability to develop and execute operational strategies that align with organizational goals.
• Strong experience managing Managed Service Providers / outsourced operations, with accountability for SLAs, vendor governance, and contract performance.
• Hands-on expertise with ITIL v4, ITSM, DevOps, and SRE practices.
• Demonstrated ability to partner with business executives and drive high customer satisfaction.
• Strong understanding of compliance and audit frameworks (SOX, PCI, GDPR, etc.).
• Application support experience with mission-critical large-scale systems such as ERP, Warehouse Management, eCommerce, Mobile Applications and Point of Sale (POS)
• Strong understanding of project management principles.
• Experience in managing organizational change related to technology and process improvements.
• Ability to gather and analyze user feedback for continuous improvement.

Explore our benefits site to discover all the perks and support we offer! From health coverage to financial and personal wellness, we've got you covered-check it out today! benefits.fivebelow.com/public/welcome

Five Below is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, age, national origin, disability, protected veteran status, gender identity or any other factor protected by applicable federal, state, or local laws.

Five Below is committed to working with and providing reasonable accommodations for individuals with disabilities. If you need a reasonable accommodation because of a disability for any part of the employment process, please submit a request and let us know the nature of your request and your contact information. crewservices.zendesk.com/hc/en-requests/new

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