Sr Director, Engineering - Digital

Senior Director of Engineering Digital

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 stakeholderstranslating 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

• 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).
• 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.
• Own end-to-end delivery and operations for e-commerce sites and mobile apps, including uptime, performance, scalability, incident management, and continuous improvement.
• Provide technical and architectural leadership for modern digital platforms, including headless commerce, content management, search, recommendations, and mobile architectures.
• 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.
• 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.

Key Digital Business & Analytics Expectations

• 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)

Qualifications

• Required Experience & Skills
• 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.
• 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.
• Preferred Experience & Skills
• 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.