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 maintai