Sr Director, Engineering - Digital

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).

• 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).

• 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.

• 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.

• Provide technical and architectural leadership for modern digital platforms
  , including headless commerce, content management,…