Strategic Program Manager, Styling Enablement

As a Styling Enablement Program Manager, you will drive execution across high-impact initiatives that shape how Styling operates and scales.

You will be directly accountable for delivering initiatives from concept through execution, ensuring cross-functional teams stay aligned, timelines are met, and work is delivered with quality in complex, fast-moving environments.

You will partner closely with Product, Engineering, Data Science, Workforce Management, Operations, and Client Support to bring new ways of working, platform improvements, and client experience enhancements to life.

You will also play a key role in improving decision quality by helping teams evaluate tradeoffs, prioritize effectively, and invest in the highest-impact opportunities.

This is an opportunity to increase the organization’s speed and effectiveness by enabling parallel execution, strengthening delivery discipline, and reducing friction across teams.

• Lead end-to-end program management for complex, cross-functional initiatives that impact Styling and the client experience
• Translate strategic priorities into clear project plans, identifying milestones, dependencies, and success metrics
• Drive cross-functional execution across teams, ensuring alignment, maintaining momentum, and holding work accountable to timelines and outcomes
• Proactively identify risks, dependencies, and blockers, and drive timely resolution to keep initiatives on track
• Use data and analysis to inform decisions, prioritize work, and ensure initiatives are grounded in clear business impact
• Enable multiple initiatives to move forward in parallel by improving coordination, clarity, and decision-making
• Develop clear, executive-ready communication on progress, risks, and key decisions
• Own the day-to-day mechanics of program delivery, including tracking progress, driving accountability, and ensuring teams can execute effectively in a complex, interdependent environment
• Support change management and adoption in partnership with enablement and communications teams
• Champion AI integration to evolve program  workflows and enhance data-driven decision-making

• You have 4–6+ years of experience in project management, business operations, strategy, or a similar role in a complex, cross-functional environment
• You have a track record of taking work from concept through delivery, balancing multiple priorities and stakeholders
• You are analytical and can structure problems, evaluate tradeoffs, and inform decisions with data
• You are an excellent cross-functional partner who can influence without authority and build alignment across teams
• You bring structure and clarity to ambiguous problems
• You are highly organized and able to manage both details and big-picture priorities
• You communicate clearly and effectively with a range of audiences, including senior leaders
• You are proactive, solutions-oriented, and motivated to improve how work gets done

• We are a group of bright, kind people who are motivated by challenge. We value integrity, innovation and trust. You’ll bring these characteristics to life in everything you do at Stitch Fix.
• We cultivate a community of diverse perspectives— all voices are heard and valued.
• We are an innovative company and leverage our strengths in fashion and tech to disrupt the future of retail. 
• We win as a team, commit to our work, and celebrate grit together because we value strong relationships.
• We boldly create the future while keeping equity and sustainability at the center of all that we do. 
• We are the owners of our work and are energized by solving problems through a growth mindset lens. We think broadly and creatively through every situation to create meaningful impact.
• We offer comprehensive compensation packages and inclusive health and wellness benefits.