Sr Director, Engineering - MP&A and Finance

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 27,000 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!

The Senior Director of Engineering – MP&A and Finance will lead the engineering organization responsible for Five Below’s Merchandise Planning & Allocation and Finance technology capabilities. This leader will own the strategy, architecture, delivery, reliability, and modernization of the platforms and integrations that support planning, allocation, demand and inventory flows, procurement and vendor processes, finance operations, accounting integrations, and related enterprise data movement across a fast-growing retail environment.

This role is a key partner to business leaders across MP&A and Finance, Product Management, Enterprise Architecture, Data/Analytics, Infrastructure, Security, and Program Management. The Senior Director will translate business strategy into technology roadmaps, operating plans, engineering execution, and measurable business outcomes while building a high-performing engineering organization that can scale with Five Below’s continued growth.

Responsibilities

1. Business, Domain, and Portfolio Leadership

· Partner with MP&A and Finance business leaders, product managers, and senior technology stakeholders to define and continuously refine the multi-year technology strategy, investment priorities, budgets, and operating plans for the domain.

· Own a strategic portfolio spanning planning, allocation, merchandising and inventory integrations, procurement-related workflows, invoice matching, GL and close-related integrations, and finance platform modernization initiatives.

· Align engineering roadmaps to business priorities such as assortment planning, platform sustainment and enhancements, pricing strategy development, technical debt reduction, modernization, scalability, security, and cost optimization.

· Define and track value realization metrics for technology investments so engineering outcomes translate into measurable business impact, operational efficiency, resilience, and financial control.

2. Engineering Delivery and Operational Excellence

· Lead end-to-end delivery and operations for mission-critical MP&A and Finance capabilities that support Five Below’s retail business, with accountability for uptime, supportability, scalability, incident management, problem management, and continuous improvement.

· Establish and continuously improve engineering and operational KPIs across quality, predictability, throughput, availability, release health, defect trends, and SLA performance.

· Drive disciplined execution across onshore, offshore, FTE, contractor, and partner teams using strong Agile delivery practices, backlog governance, estimation rigor, and clear accountability for outcomes.

· Partner with operations and support teams to perform root cause analysis on complex incidents, reduce repeat failures, and improve production resilience through better observability, automation, and preventive controls.

3. Architecture, Platforms, and Modernization

· Provide architectural and technical leadership across a hybrid enterprise landscape that includes packaged platforms, custom services, integrations, cloud data pipelines, and operational tooling supporting MP&A and Finance workflows.

· Lead modernization across the current platform ecosystem, including technologies and vendors such as Oracle Retail/RMS, Oracle Fusion, Oracle OIC, O9, Bamboo Rose, Databricks, Kafka, MongoDB, Airflow/Astronomer, and Azure-native integration and data services where applicable.

· Drive engineering strategies that reduce operational fragility and cost, including API and event-driven integration patterns, CI/CD automation, configuration modernization, stronger monitoring, and improved cloud efficiency.

· Oversee technical debt and lifecycle management for the domain, including vendor-mandated upgrades, security and authentication changes, archiving and retention needs, performance improvements, and platform simplification efforts.

4. Governance, Risk, Compliance, and Financial Stewardship

· Ensure applications, data flows, and engineering practices meet enterprise architecture, security, governance, SOX, audit, and risk management requirements, with strong emphasis on traceability, controls, secure design, and reliable change management.

· Lead budgeting, capacity planning, vendor spend management, and resource allocation for the MP&A and Finance engineering portfolio, aligning spend to business capabilities and strategic outcomes.

· Support senior leadership with strategic analysis of emerging capabilities, platform investments, and build-vs-buy decisions by evaluating business value, ROI, cost, risk, scalability, and long-term maintainability.

5. Stakeholder, Vendor, and Partner Leadership

· Serve as a trusted technology partner to business and product leaders across MP&A and Finance, acting as the primary senior engineering point of contact for strategy, execution, trade-offs, and escalation.

· Lead vendor and implementation partner relationships across the domain, including selection, governance, performance management, commercial value realization, and adherence to Five Below engineering standards.

· Represent the engineering organization in portfolio governance, business reviews, recruiting, and external partnership conversations that help elevate Five Below’s technology brand and delivery capability.

6. People Leadership and Organizational Development

· Build and lead a high-performing engineering organization that includes directors, managers, engineers, contractors, and partner resources supporting MP&A and Finance capabilities.

· Foster an inclusive, supportive, and high-accountability culture grounded in growth, learning, recognition, and clear career development for both associates and leaders.

· Coach and develop engineering leaders to operate at scale across delivery, architecture, operations, and business partnership responsibilities.

Qualifications

Required Experience and Skills

· 12+ years of progressive experience in software engineering, enterprise applications, or technology delivery, with significant depth in retail, merchandising, planning, allocation, finance, or adjacent enterprise domains.

· 7+ years leading managers and/or directors responsible for the delivery and operations of business-critical enterprise platforms in a high-growth environment.

· Strong experience implementing and supporting MP&A and Finance technology capabilities such as merchandizing, allocation, demand forecasting, ERP, merchandise financial planning, vendor management, purchase order management, finance integrations, and related operational workflows.

· Demonstrated experience partnering with senior business and product leaders to convert domain strategy into roadmaps, budgets, operating plans, and measurable engineering outcomes.

· Deep experience with enterprise integration and data ecosystems, including API, event-driven, and batch/file integration patterns across platforms such as Oracle RMS, Oracle Fusion, OIC, O9, Bamboo Rose, Databricks, Kafka, MongoDB, and cloud-native services.

· Strong engineering leadership in reliability, observability, CI/CD, automated testing, release management, incident/problem management, and operational excellence.

· Experience operating within governance, ris