Sr Director, Engineering - Digital

Five Below•Philadelphia, PA

About The Position

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).

Requirements

12+ years of progressive experience in software engineering and technology, with significant focus on customer-facing digital products (e-commerce websites and native mobile applications).
7+ years leading and scaling engineering teams (including managers/directors) responsible for delivery and operations of high-traffic, business-critical digital experiences.
Proven track record leading engineering teams for high-growth retail or consumer businesses, with accountability for uptime, stability, performance, and security of digital platforms.
Demonstrated success partnering with Digital, Marketing, and Product leaders to drive measurable improvements in digital business outcomes (traffic, conversion, AOV, retention, performance).
Strong experience with omni-channel digital capabilities such as e-commerce, OMS, BOPIS, ship-from-store, and marketplace integrations.
Deep understanding of modern web and mobile architectures, including microservices, APIs, event-driven systems, and cloud-native design.
Expertise with headless and composable commerce architectures, ideally with experience on MACH-aligned platforms (e.g., CommerceTools or similar).
Strong experience driving DevOps/DevSecOps, CI/CD, automated testing, monitoring/alerting, and incident/problem management in production environments.
Demonstrated ability to set and manage engineering and operational KPIs, communicate them to stakeholders, and drive continuous improvement.
Exceptional communication and storytelling skills, with the ability to engage both technical and non-technical audiences, influence decisions, and align cross-functional teams.
High degree of business acumen, able to connect engineering decisions to customer experience, P&L impact, and strategic outcomes.

Nice To Haves

Experience in high-volume retail or consumer brands with strong digital and omni-channel businesses.
Experience with digital analytics and experimentation platforms (e.g., Adobe/GA, Optimizely, LaunchDarkly, or similar) and working closely with data/analytics teams.
Familiarity with SEO, site performance optimization, and mobile performance best practices.
Experience operating in a matrixed environment, collaborating across multiple functional and product domains.
Experience with governance, risk, and compliance practices, including SOX and audit considerations, especially as they relate to digital platforms.

Responsibilities

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).
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.
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.
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 controls, monitoring and alerting). Ensure applications and data comply with governance, risk, compliance, SOX, and audit policies, including appropriate logging, monitoring, and automated controls. Stay ahead of market, technology, and digital experience trends, bringing forward recommendations on tools, platforms, and practices that will improve customer experience and engineering productivity. Develop and maintain technical roadmaps for digital platforms and capabilities, clearly communicating modernization paths and key architectural decisions.
People Leadership & High-Performance Culture: Build, lead, and inspire high-performing engineering teams (including Engineering Managers/Directors) delivering exceptional web and mobile experiences in a fast-paced, high-growth retail environment. Foster an inclusive culture grounded in The Five Below Way, emphasizing psychological safety, accountability, continuous learning, and recognition. Develop and execute talent strategies for hiring, onboarding, performance management, and career development across both FTEs and contractors. Provide ongoing coaching and mentorship to engineering leaders and senior engineers, growing capabilities in architecture, product thinking, and operational excellence. Ensure contractors and partners are fully integrated into team rituals, quality practices, and feedback loops to achieve consistent delivery excellence. Represent the engineering organization in recruiting, external partnerships, and thought leadership to help elevate Five Below’s technology brand in the market.
Vendor, Partner & Ecosystem Management: Lead relationships with digital and engineering vendors (e.g., commerce platforms, mobile partners, development and implementation partners, cloud providers), ensuring high-quality delivery, scalability, and cost-effectiveness. Evaluate and benchmark vendor performance, ensuring clear SLAs, accountability, and continuous improvement. Make informed build vs. buy decisions in partnership with Product, Architecture, and Finance, balancing speed, cost, risk, and strategic differentiation.
Key Digital Business & Analytics Expectations: Deeply understand and help shape key digital business metrics, including but not limited to: Traffic and acquisition (organic, paid, campaign-driven) Conversion rate and funnel performance (browse → PDP → cart → checkout → confirmation) Average order value (AOV) and attach rate Repeat purchase rate, retention, and loyalty engagement Site and app performance (page load, Core Web Vitals, crash rate, latency) Partner with Digital and Marketing teams, Data/Analytics, and Product to define measurement frameworks, dashboards, and experimentation strategies to improve these metrics. Ensure engineering teams understand how their work moves the metrics, using data and insights to guide prioritization and solution design.