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Strategy Lead, Software

Wayfair

$112,000 - $123,500
Aug 14, 2025
Boston, MA, US
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Wayfair is seeking to optimize its software investments and create a centralized approach to software purchasing, governance, and optimization.

Requirements

  • 5+ years of experience in a strategy or operational role with a strong track record using data to identify insights, creating new processes, influencing, and driving results.
  • Strong financial acumen, a data-driven approach to decision-making, and the ability to identify trends within datasets to drive decision-making.
  • Ability to use data to break down components of purchases and drive the right conversations around the decisions we need to make.
  • Negotiation experience and/or an understanding of the Software/Cloud landscape is a plus but not required (we can teach you).
  • A highly organized project manager who can juggle multiple priorities, drive cross-functional initiatives, and ensure flawless execution.
  • A proactive self-starter who is comfortable working in a fast-paced, evolving environment.
  • Experience with cloud infrastructure and software purchasing strategies is preferred.

Responsibilities

  • Oversee Wayfair’s entire software portfolio—commercial strategy, governance, financial discipline, and long-term planning—across all business units and functions.
  • Partner with business, tech, and product leaders to define and drive our strategy for emerging areas (ex. GenAI), identify use cases, and map short- and long-term implementation roadmaps.
  • Support cloud infrastructure commercial negotiations and partner with technical and business stakeholders to evaluate tradeoffs and shape long-term cloud purchasing strategies.
  • Serve as the key partner to FP&A for forecasting and managing software spend. Build frameworks to evaluate ROI, align spend with business goals, and track impact.
  • Design and evolve software governance processes to ensure technology decisions are timely, strategic, and consistent with Wayfair’s broader priorities.
  • Proactively identify opportunities for consolidation and simplification of software tools. Align roadmaps across stakeholders to realize value and reduce redundancy.
  • Act as a trusted advisor to Engineering, Product, Finance, Legal, and the Executive team on major software decisions and enterprise tech strategy.

Other

  • Bachelor’s degree required and preferred in an analytical field, such as economics, math, statistics, supply chain management, analytics, or engineering. MBA is a plus.
  • Strong leadership, communication, and interpersonal skills, with the ability to influence and collaborate effectively at all levels of the organization and across different teams.
  • A strategic thinker who thrives in ambiguity and is excited by the opportunity to shape and define a new area.
  • 4 days in office/ 1 day WFH
  • Restricted stock units may be provided as part of the compensation package, in addition to a full range of medical, financial, and/or other benefits, dependent on the position offered.