Program Manager, Styling Enablement

About the Role

As the Styling Enablement Program / Project Manager, you will play a critical role in driving execution across high-impact initiatives that shape how Styling operates and scales. This role is responsible for translating strategy into action by managing complex, cross-functional programs that support platform evolution, new ways of working, and improved experiences for both clients and stylists.

This is an opportunity to create meaningful impact by enabling parallel execution of enterprise priorities, strengthening delivery discipline, and helping the organization move faster without sacrificing quality or stability.

Reporting to the Director of Styling Enablement & Planning, you will partner closely with leaders and teams across Product, Engineering, Data Science, Workforce Management, Operations, and Client Support. Your ability to manage ambiguity, align stakeholders, and deliver clear outcomes will directly contribute to Stitch Fix’s continued evolution toward more proactive, AI-powered, and relationship-driven styling.

You're excited about this opportunity because you will…

• 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

We’re excited about you because…

• You have 4–6+ years of experience in program management, operations, enablement, or a related role supporting complex, cross-functional initiatives
• You have a proven track record of managing work from concept through delivery, balancing competing priorities in dynamic environments
• You excel at building strong partnerships and influencing without authority across diverse teams
• You are highly organized and detail-oriented, with the ability to see both the big picture and the execution details
• You communicate clearly and confidently, tailoring messages for different audiences, including senior leaders
• You are comfortable navigating ambiguity and bringing structure to complex problems
• You are proactive, solutions-oriented, and motivated by creating clarity and momentum
• Above all, you are bright, kind, and motivated to make an impact

Why you'll love working at Stitch Fix...

• 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.