Sr Director, Engineering - Digital

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! POSITION SUMMARY   The   Senior Director of Engineering – Digital   will lead the engineering organization responsible for Five Below’s   customer-facing digital experiences   across   e-commerce websites and native mobile apps , including capabilities like product discovery, cart & checkout, loyalty, personalization, and omni-channel flows such as   BOPIS, ship-from-store, and marketplace . This leader will own the architecture, delivery, and operations of mission-critical digital platforms that power our omni-channel growth, ensuring high performance, reliability, and security at scale.   Reporting directly to the   VP of Engineering , this role will be a key partner to   Digital and Digital Marketing leaders , Product, Data/Analytics, and other business stakeholders—translating business strategy and customer insights into technology roadmaps, engineering outcomes, and measurable business impact. The Senior Director will build and lead   high-performing, modern engineering teams , driving best-in-class engineering practices, experimentation, and data-driven decision making to continuously improve key digital   business metrics   (e.g., traffic, conversion rate, AOV, retention, performance, and uptime).   RESPONSIBILITIES   1. Digital & Business Strategy Leadership   Partner with   Digital   and   Marketing   business leaders   to define a multi-year technology strategy and roadmap for web and mobile experiences aligned to business vision, OKRs, and customer outcomes.   Translate business objectives (traffic, conversion, AOV, customer lifetime value, acquisition costs, campaign performance) into clear   engineering goals, KPIs, and investment priorities .   Oversee execution of a   strategic digital technology portfolio , balancing roadmap delivery, technical debt reduction, platform modernization, and innovation.   Define and track   value realization metrics   for digital technology investments, ensuring engineering outcomes drive measurable business impact (e.g., improved site/app performance, increased conversion, reduced checkout friction).   Support senior management with strategic analysis of new and emerging digital capabilities (e.g., personalization, search, recommendations, experimentation, content management, SEO, performance optimization) to determine customer impact and financial viability (ROI).   2. Product & Stakeholder Partnership   Serve as a   trusted technology partner   to Digital, Digital Marketing, and cross-functional leaders (Product Management, Data/Analytics, UX, Merchandising, Supply Chain, and Stores where relevant to omni experiences).   Shape and refine   product and platform backlogs   in partnership with Product Management, ensuring clear prioritization across growth, customer experience, technical health, and compliance.   Establish and maintain strong communication and stakeholder management practices, setting expectations on timelines, trade-offs, and risks while ensuring alignment across business and technology.   Represent digital engineering in key governance, portfolio, and investment discussions.   3. Digital Engineering Delivery & Operations   Own end-to-end delivery and operations for   e-commerce sites and mobile apps , including uptime, performance, scalability, incident management, and continuous improvement.   Ensure high-quality, timely delivery through robust   Agile practices , predictable release management, and strong engineering execution across onshore and offshore teams.   Establish and continuously improve   engineering and operational KPIs , including lead time, deployment frequency, change failure rate, MTTR, defects per story, velocity, and SLA adherence.   Partner with operations/SRE teams to conduct root cause analysis on complex incidents, drive systemic fixes, and improve reliability.   Manage departmental budgets, resource allocations, and vendor spend, aligning investments to digital initiatives and capability outcomes.   Drive a culture of data-driven decision-making and   experimentation   (A/B testing and related methods) to improve conversion, engagement, and retention.   4. Architecture, Platforms & Engineering Excellence   Provide technical and architectural leadership for   modern digital platforms , including headless commerce, content management, search, recommendations, and mobile architectures.   Lead the evolution of our   composable, headless, MACH-aligned architecture   (Microservices, API-first, Cloud-native, Headless), ensuring flexibility and scalability of digital experiences; experience with CommerceTools or similar platforms is a plus.   Ensure robust engineering standards across coding, design, documentation, testing, security, and performance; champion best practices such as   code reviews, automated testing, pipeline automation, and code sharing .   Partner with Enterprise Architecture, Data, and Infrastructure/Security teams to ensure alignment with enterprise standards, security policies, and cloud strategies (multi-cloud footprint such as AWS, Azure, GCP, or Oracle Cloud).   Drive   DevSecOps and CI/CD   adoption to increase deployment speed, reduce risk, and improve quality (shift-left testing, automated cont