Sr Director, Engineering - MP&A and Finance

Five Below•Philadelphia, PA

About The Position

At Five Below, our growth is fueled by associates 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!' This role is the senior product leader accountable for the strategy, roadmap, business outcomes, and product operating model across Five Below’s Merchandise Planning & Allocation (MP&A) domain. This position serves as the product counterpart to engineering leadership for the domain, ensuring that Five Below’s planning, assortment, allocation, replenishment, and related merchandising workflows are supported by products aligned with business processes, measurable outcomes, and long-term scalability. The current MP&A landscape presents significant opportunities for simplification and modernization, with fragmented systems, manual processes, and limited visibility. This leader will collaborate deeply with Merchandising, Planning, Allocation, Inventory, Merch Operations, Product, Engineering, Architecture, Data/Analytics, and enterprise stakeholders to define the future product direction for MP&A, translating business strategy into a clear product vision, measurable KPIs, prioritized roadmaps, and high-quality execution.

Requirements

12+ years of experience in product management, product ownership, business product leadership, or closely related roles, with significant depth in retail, merchandising, planning, allocation, or inventory-related domains.
5+ years leading product managers or cross-functional product organizations in complex enterprise environments.
Deep understanding of MP&A business processes, including merchandise financial planning, assortment planning, forecasting, allocation, replenishment, in-season management, and merchandising operational workflows.
Demonstrated experience owning domain strategy, roadmaps, prioritization, and measurable outcomes across complex platforms or multi-team initiatives.
Ability to define meaningful KPIs, use data to prioritize, and connect product decisions to business performance and operational outcomes.
Strong experience translating complex business process needs into clear product requirements, epics, and phased roadmaps.
Proven partnership with Engineering, Architecture, Data, and business stakeholders in Agile delivery environments.
Excellent executive communication, facilitation, and stakeholder management skills.

Nice To Haves

Experience with Five Below-relevant platforms and ecosystems such as o9, Oracle Retail/RMS, Bamboo Rose, assortment tools, replenishment and allocation systems, Databricks, Power BI, and adjacent merchandising platforms.
Experience leading product work through platform evaluation, package fit assessment, vendor selection, or large-scale business and technology transformation.
Familiarity with product frameworks such as journey mapping, JTBD, outcome-based roadmapping, prioritization models, and operational KPI frameworks.
Experience in environments with significant manual processes, spreadsheet dependence, fragmented tooling, and the need to modernize toward more integrated and governed product ecosystems.

Responsibilities

Own the multi-year product vision and strategy for the MP&A domain, aligned to Five Below’s business priorities, enterprise strategy, and long-range planning needs.
Define the target product landscape and business capability model across core MP&A processes such as merchandise financial planning, assortment planning, demand forecasting, inventory acquisition and replenishment, seasonal allocation, in-season performance management, and related planning workflows.
Ensure product strategy reflects Five Below’s current reality: disconnected tools, manual handoffs, limited automation, inconsistent data definitions, and workflow friction that constrain scale and decision quality.
Establish clear domain north stars and guardrails that connect product investments to business outcomes, user productivity, and operational resilience.
Develop deep understanding of the end-to-end MP&A process, including preseason planning, in-season adjustments, assortment development, item setup, PO requests and PO management, allocation review, DC split decisions, and sell-through monitoring, MFP, Assortment planning.
Lead process discovery and working sessions with business partners to document current-state journeys, pain points, handoffs, controls, and opportunities for standardization, simplification, and automation.
Translate business process needs into product requirements that are grounded in how planners, buyers, allocators, and merch operations teams actually work.
Maintain a strong point of view on where Five Below should adopt standard package capabilities, where configuration is sufficient, and where differentiated workflows or microapps are required.
Own the MP&A domain roadmap and backlog, framing problems clearly, sequencing work intentionally, and balancing business value, urgency, risk, complexity, adoption readiness, and cost.
Prioritize between short-term continuity and long-term transformation, including targeted improvements to existing platforms while defining the future-state process and product architecture.
Lead product evaluation, build-vs-buy thinking, and vendor/RFP decision support for major MP&A platform decisions.
Drive quarterly and multi-year roadmap planning with explicit linkage to business objectives, capability maturity, delivery feasibility, and organizational capacity for change.
Define and manage the key product and business KPIs for the MP&A domain, including measures such as forecast accuracy, planning cycle time, inventory productivity, and the ability to scale profitable assortments across seasons.
Establish additional domain measures that reflect the realities of Five Below’s operating model, such as planner productivity, adoption of in-system workflows, reduction in offline spreadsheets, data freshness, PO lifecycle visibility, vendor compliance, and speed of in-season decision-making.
Use both quantitative and qualitative data to frame problems, assess product-market fit inside the enterprise, validate roadmap choices, and prove value realization after release.
Ensure teams understand how product changes are expected to move business outcomes such as sales, margin, inventory health, and operational efficiency.
Lead senior product managers and cross-functional product squads through discovery, requirements, design, build, launch, adoption, and post-release learning.
Partner closely with Engineering, Architecture, Data, and Operations to ensure solutions are scalable, resilient, supportable, and well integrated with upstream and downstream systems.
Drive strong product management fundamentals across the team, including hypothesis-driven discovery, clear outcome definition, backlog hygiene, requirements quality, prioritization discipline, roadmap storytelling, and release readiness.
Partner with Engineering and Operations on operational KPIs and service expectations for key planning platforms, including data freshness, job success, planning cycle SLAs, and issue resolution.
Serve as the senior product partner for MP&A business leadership, building trusted relationships and ensuring the roadmap reflects both strategic priorities and practical process realities.
Lead cross-functional governance for major product decisions, trade-offs, and sequencing decisions across business, product, engineering, architecture, and data stakeholders.
Communicate product strategy, roadmap, risks, progress, and outcomes clearly to executive stakeholders and working teams.
Help the organization navigate change thoughtfully by balancing ambition with adoption readiness, training needs, process redesign, and the business’s capacity to absorb complexity.
Build, lead, and coach a high-performing product team for MP&A, including senior product managers and other product practitioners supporting the domain.
Mentor team members on domain expertise, product craft, stakeholder management, KPI thinking, and enterprise product leadership.
Create a product culture grounded in accountability, clarity, curiosity, strong business partnership, and continuous improvement.