Director, Software Engineering - AI

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 20,000 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!

RESPONSIBILITIES

• Drive AI initiatives from exploration to proof of concept, with a focus on business impact.
• Collaborate with product, data, and business teams to identify and prioritize opportunities.
• Provide technical leadership to a small team, vendors, and partners; guide experimentation and implementation.
• Stay current on emerging AI trends (e.g., generative AI, agentic AI) and assess their applicability to retail.
• Manage vendor relationships and budgets, ensuring value from partnerships.
• Contribute to overall engineering architecture and best practices for scalable data and AI systems.
• Takes full ownership of complex projects, ensuring definition, documentation, and the use of appropriate project management tools and processes.
• Oversees project resources, financials, and effectively manages the expectations of key stakeholders.
• Manage department budgets, invoices and allocations, inclusive of alignment to appropriate business initiative/capability
• Identifies and addresses stakeholder communication needs, translating engagement strategies into actionable deliverables.
• Serves as a primary contact for stakeholders, facilitating open discussions, promoting understanding, and disseminating key technical and business information.
• Oversees vendor relationships, ensuring performance aligns with key indicators, and addresses potential disputes or conflicts proactively.
• Utilizes vendor performance data for benchmarking, informs development roadmaps with vendor expertise, and manages service improvements while considering contract negotiations.
• Contributes to solution architectures across specific domains, evaluating alternatives based on cost, performance, and scalability, while documenting key decisions.

QUALIFICATIONS

• 7+ years' experience in Information Technology with experience related to application development, IT operations management, cloud infrastructure management, project/program management, or technology consulting
• Proven track record of delivering AI solutions from concept to production, with measurable business impact in complex, data-rich environments.
• Deep understanding of modern AI/ML concepts, including generative AI, large language models (LLMs), MLOps, and retrieval-augmented generation (RAG), with the ability to apply them to real-world business challenges.
• Demonstrated experience leveraging cloud-scale data platforms such as Databricks for AI model development, training, deployment, and monitoring.
• Strong grasp of data engineering, governance, and quality practices as they apply to AI initiatives, ensuring secure, ethical, and reliable outcomes.
• Ability to translate business needs-particularly in retail operations, supply chain, and customer engagement-into AI opportunities and actionable roadmaps.
• Skilled in leading cross-functional teams of engineers, data scientists, and product stakeholders to rapidly prototype, iterate, and scale AI solutions.
• Knowledge of AI/ML toolchains, frameworks, and APIs (e.g., PyTorch, TensorFlow, MLflow, Hugging Face, vector databases) and their practical application in enterprise settings.
• Familiarity with responsible AI principles, bias mitigation, and compliance considerations relevant to large-scale retail operations.Experience in building highly productive engineering teams responsible for delivery, uptime, stability and operations of all applications and systems in a high-growth, omni-channel retailer
• Expertise in formulating and implementing operating processes, procedures and routines, such as incident management, automated monitoring and alerting, capacity planning, build versus buy decision making
• Expertise in open-source software development languages & frameworks such as Java, Spring, NO-SQL DB's, Spark, Kafka, Databricks, Cloud computing
• Experience in Governance, Risk and Compliance management, specifically around implementing automated controls, security monitoring, enabling audit trails, securing data and complying to company's SOX and audit policies
• Expertise in building and deploying secure applications in a multi-cloud footprint (AWS, Azure, GCP or Oracle cloud)
• Expertise driving efficiencies across the application footprint through automation leveraging CI/CD and DevSecOps (shift-left) methodologies
• Highest level of personal integrity, and the ability to professionally handle confidential matters and exude the appropriate level of judgment and maturity

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. crewservices.zendesk.com/hc/en-us/requests/new

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