Sr Director, Engineering - Digital
4 days ago
Philadelphia
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). • 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., • 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., • 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