Sr Director, Engineering - Digital

POSITION SUMMARY

TheSenior Director of Engineering 6 Digitalwill lead the engineering organization responsible for Five Below 27sa0customer-facing digital experiencesacrossa0e-commerce websites and native mobile apps, including capabilities like product discovery, cart & checkout, loyalty, personalization, and omni-channel flows such asBOPIS, 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 theVP of Engineering, this role will be a key partner toDigital and Digital Marketing leaders, Product, Data/Analytics, and other business stakeholders 6translating business strategy and customer insights into technology roadmaps, engineering outcomes, and measurable business impact. The Senior Director will build and leadhigh-performing, modern engineering teams, driving best-in-class engineering practices, experimentation, and data-driven decision making to continuously improve key digitalbusiness metrics(e.g., traffic, conversion rate, AOV, retention, performance, and uptime).

RESPONSIBILITIES

1. Digital & Business Strategy Leadership

• Partner withDigitalanda0Marketingbusiness leadersto 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 clearengineering goals, KPIs, and investment priorities.

• Oversee execution of astrategic digital technology portfolio, balancing roadmap delivery, technical debt reduction, platform modernization, and innovation.

• Define and trackvalue realization metricsfor 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 atrusted technology partnerto Digital, Digital Marketing, and cross-functional leaders (Product Management, Data/Analytics, UX, Merchandising, Supply Chain, and Stores where relevant to omni experiences).

• Shape and refineproduct and platform backlogsin 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 fore-commerce sites and mobile apps, including uptime, performance, scalability, incident management, and continuous improvement.

• Ensure high-quality, timely delivery through robustAgile practices, predictable release management, and strong engineering execution across onshore and offshore teams.

• Establish and continuously improveengineering 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 andexperimentation(A/B testing and related methods) to improve conversion, engagement, and retention.

4. Architecture, Platforms & Engineering Excellence

• Provide technical and architectural leadership formodern digital platforms, including headless commerce, content management, search, recommendations, and mobile architectures.

• Lead the evolution of ourcomposable, 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 ascode 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).

• DriveDevSecOps and CI/CDadoption 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 ofmarket, technology, and digital experience trends, bringing forward recommendations on tools, platforms, and practices that will improve customer experience and engineering productivity.

• Develop and maintaintechnical roadmapsfor digital platforms and capabilities, clearly communicating modernization paths and key architectural decisions.

5. People Leadership & High-Performance Culture

• Build, lead, and inspirehigh-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 inThe 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 ongoingcoaching and mentorshipto 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 27s technology brand in the market.

6. Vendor, Partner & Ecosystem Management

• Lead relationships withdigital 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 informedbuild vs. buydecisions in partnership with Product, Architecture, and Finance, balancing speed, cost, risk, and strategic differentiation.

Key Digital Business & Analytics Expectations

• Deeply understand and help shape keydigital business metrics, including but not limited to:

• Traffic and acquisition (organic, paid, campaign-driven)

• Conversion rate and funnel performance (browse 6 PDP 6 cart 6 checkout 6 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 definemeasurement frameworks, dashboards, and experimentation strategies to improve these metrics.

• Ensure engineering teams understandhow their work moves the metrics, using data and insights to guide prioritization and solution design.

QUALIFICATIONS

Required Experience & Skills

• 12+ yearsof progressive exper