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Five Below Logo

Director – Software Engineering - AI

Five Below

Salary not specified
Sep 9, 2025
Philadelphia, PA, USA
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Five Below is looking to drive AI initiatives from exploration to proof of concept, with a focus on business impact, to identify and prioritize opportunities and stay current on emerging AI trends applicable to retail.

Requirements

  • 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.
  • Knowledge of AI/ML toolchains, frameworks, and APIs (e.g., PyTorch, TensorFlow, MLflow, Hugging Face, vector databases) and their practical application in enterprise settings.
  • 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 building and deploying secure applications in a multi-cloud footprint (AWS, Azure, GCP or Oracle cloud)

Responsibilities

  • Drive AI initiatives from exploration to proof of concept, with a focus on business impact.
  • 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.
  • 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.
  • Contributes to solution architectures across specific domains, evaluating alternatives based on cost, performance, and scalability, while documenting key decisions.
  • Oversees vendor relationships, ensuring performance aligns with key indicators, and addresses potential disputes or conflicts proactively.

Other

  • Collaborate with product, data, and business teams to identify and prioritize opportunities.
  • Manage vendor relationships and budgets, ensuring value from partnerships.
  • 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
  • Highest level of personal integrity, and the ability to professionally handle confidential matters and exude the appropriate level of judgment and maturity