Sr Director, Engineering - Digital

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).

RESPONSIBILITIES

1. 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).

2. 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.

3. 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.

4. 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.

5. 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.

6. 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 diff