Director of Wholesale Strategy & Operations

Whoop · Boston, MA

WHOOP is seeking a highly analytical, operationally rigorous, and strategic Director of Wholesale Strategy & Operations to help scale and optimize our global retail and wholesale business. This highly cross-functional leadership role will serve as a key operational partner to the Wholesale Sales & Marketing organization, driving strategic initiatives, forecasting processes, operational performance management, and cross-functional execution across multiple retail channels and international markets.

This individual will act as connective tissue across Sales, Operations, Finance, Compliance, Legal, Analytics, and Marketing — ensuring complex initiatives are executed efficiently, risks are proactively managed, and the wholesale business is positioned for scalable growth.

The ideal candidate is a structured problem solver, exceptional communicator, and highly effective cross-functional operator who thrives in fast-paced, ambiguous environments. They combine strong analytical capabilities with operational leadership and are comfortable influencing stakeholders across all levels of the organization.

RESPONSIBILITIES:

  • Lead and drive cross-functional strategic initiatives across WHOOP’s wholesale and retail business, ensuring alignment across Sales, Operations, Finance, Legal, Compliance, Analytics, and Marketing teams

  • Serve as the operational lead for key commercial programs, managing timelines, dependencies, stakeholder communication, and execution against business objectives

  • Own and evolve wholesale forecasting processes, partnering closely with Sales and Operations to assess retailer-level demand forecasts, identify risks and opportunities, and improve forecast accuracy

  • Develop scalable reporting frameworks and executive-level business reviews across retailer performance, operational KPIs, returns trends, and commercial health metrics

  • Partner with Operations to monitor and improve wholesale operational performance, surfacing gaps against KPIs/OKRs and driving corrective action plans where necessary

  • Oversee retailer returns reporting and analysis across regions, identifying trends, operational inefficiencies, and opportunities for process improvement

  • Support complex contract negotiations and retailer onboarding initiatives by coordinating closely with Legal, Finance, Operations, and Compliance teams

  • Represent the Wholesale organization in new market expansion and retail launch discussions, helping evaluate operational readiness, compliance requirements, timelines, and go-live feasibility

  • Establish scalable operational processes and governance frameworks that improve organizational efficiency and enable future growth

  • Leverage AI, automation, and data tooling to improve business intelligence, operational workflows, forecasting accuracy, and decision-making capabilities

  • Influence senior leadership through clear communication, data-driven storytelling, and strategic recommendations that support business planning and prioritization

  • Build strong cross-functional relationships and operate as a trusted partner across commercial and operational teams

  • QUALIFICATIONS:

  • 10+ years of experience in strategy, operations, sales operations, commercial planning, consulting, analytics, or related business functions within high-growth consumer, technology, or retail organizations

  • Proven experience leading complex cross-functional initiatives with measurable business impact across multiple stakeholder groups

  • Strong analytical and financial acumen, with experience managing forecasting, operational planning, KPI development, and business performance analysis

  • Experience supporting or leading retailer operations, wholesale planning, commercial operations, or go-to-market execution

  • Demonstrated ability to influence senior stakeholders and drive alignment across diverse functional teams

  • Exceptional organizational and program management skills, with the ability to manage multiple high-priority initiatives simultaneously

  • Strong communication and executive storytelling capabilities, including experience presenting to leadership audiences

  • Advanced proficiency in Excel/Google Sheets and familiarity with BI/data tools such as Sigma, Tableau, SQL, or similar platforms

  • Experience leveraging AI tools and automation to improve workflows, analysis, and operational efficiency

  • Entrepreneurial mindset with a high degree of ownership, adaptability, and comfort operating in ambiguity

  • Experience managing and developing team members is preferred

  • Passion for health, fitness, and performance



  • Operations pay context

    Based on 4,497 disclosed Operations salaries on RoleSuite, the role pays a median of $109K/year, with most offers between $82K and $144K (10th–90th percentile: $66K–$184K).

    This posting lists $155K–$195K, above the $109K market median.

    See the full Operations salary breakdown →
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