Sr Director, Engineering - Digital

Five Below, Inc.; Philadelphia (Philadelphia County); On-site; USD 150,000 - 200,000; Full time

Job summary

Five Below, Inc. is seeking a Senior Director to lead high-performing engineering teams focused on modern digital strategies. The role involves shaping product backlogs, managing omni-channel capabilities, and driving data-driven decision making. Ideal candidates will have robust experience in software engineering, e-commerce, and a knack for balancing technical innovations with business acumen. This position is crucial in ensuring the architectural evolution aligns with market trends, enhancing customer experience across all digital platforms.

Qualifications

• 5+ years of progressive experience in software engineering and technology.
• Experience with omni-channel digital capabilities (e-commerce, OMS).
• Familiarity with SEO, site performance optimization.

Responsibilities

• Shape and refine product and platform backlogs with Product Management.
• Lead evolution of MACH-aligned architecture.
• Stay ahead of market and technology trends.

Skills

Software engineering

Omni-channel digital capabilities

DevOps/DevSecOps

CI/CD

Communication skills

Business acumen

Tools

CommerceTools

Adobe/GA

Optimizely

LaunchDarkly

Job description

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 Shape and refine **product and platform backlogs** in partnership with Product Management, ensuring clear prioritization across growth, customer experience, technical health, and compliance. 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. 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. QUALIFICATIONS **Required Experience & Skills** of progressive experience in software engineering and technology, with significant focus on Strong experience with **omni-channel digital capabilities** such as e-commerce, OMS, BOPIS, ship-from-store, and marketplace integrations. 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. Five Below is a leading growth retailer offering trend-right, extreme value, high-quality products loved by the kid and the kid in all of us. We believe life is better when customers are free to "let go & have fun" in an amazing experience filled with unlimited possibilities. With most items priced between $1 and $5 and some extreme-value items priced beyond $5, Five Below makes it easy to say YES! to the newest, coolest stuff across awesome Five Below worlds: Candy, Style, Party, Room, Create, Tech, Sports, and New & Now. Founded in 2002 and headquartered in Philadelphia, Pennsylvania, Five Below today has over 1,900 stores in 46 states.