Sr Director, Engineering - Digital

Five Below Inc; Philadelphia (Philadelphia County); On-site; USD 150,000 - 190,000; Full time

Job summary

Five Below is seeking a Senior Director of Engineering – Digital to lead engineering for our customer-facing experiences across e-commerce and native apps. You will own architecture, delivery, and operations of digital platforms, partnering with Digital, Marketing, Product, and Data teams to translate business strategy into measurable technical outcomes.

You’ll drive a high-performance culture, adopt modern DevOps practices, and champion scalable, secure, and resilient systems.

Qualifications

• 12+ years in software engineering and technology leadership for customer-facing digital products.
• 7+ years leading and scaling engineering teams in high-growth environments.
• Proven track record improving digital metrics (traffic, conversion, AOV, retention).

Responsibilities

• Define multi-year technology strategy for web and mobile experiences.
• Partner with product, marketing, and analytics to align roadmaps with business outcomes.
• Lead end-to-end delivery and operations for e-commerce sites and mobile apps; ensure uptime and performance.
• Drive modern digital architecture and MACH-aligned practices; advance headless commerce.

Skills

Engineering leadership

Digital strategy

Stakeholder management

Cloud-native architectures

DevOps/DevSecOps

Headless/ MACH architecture

API-first design

Tools

CommerceTools

Adobe Analytics

LaunchDarkly

CI/CD tooling

Job description

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

• 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).
• 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.
• 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.
• 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.
• 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.
• 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 differentiation.

QUALIFICATIONS

• 12+ years of progressive experience in software engineering and technology, with significant focus on customer-facing digital products (e-commerce websites and native mobile applications).
• 7+ years leading and scaling engineering teams (including managers/directors) responsible for delivery and operations of high-traffic, business-critical digital experiences.
• Proven track record leading engineering teams for high-growth retail or consumer businesses, with accountability for uptime, stability, performance, and security of digital platforms.
• Demonstrated success partnering with Digital, Marketing, and Product leaders to drive measurable improvements in digital business outcomes (traffic, conversion, AOV, retention, performance).
• Strong experience with omni-channel digital capabilities such as e-commerce, OMS, BOPIS, ship-from-store, and marketplace integrations.
• Deep understanding of modern web and mobile architectures, including microservices, APIs, event-driven systems, and cloud-native design.
• 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.

Explore our benefits site to discover all the perks and support we offer! From health coverage to financial and personal wellness, we've got you covered—check it out today! benefits.fivebelow.com/public/welcome

Five Below is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, age, national origin, disability, protected veteran status, gender identity or any other factor protected by applicable federal, state, or local laws. Five Below is committed to working with and providing reasonable accommodations for individuals with disabilities. If you need a reasonable accommodation because of a disability for any part of the employment process, please submit a request and let us know the nature of your request and your contact information.

Careers Site 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.