Principal Program Manager

At Jiffy.com, we’re redefining how crafters, small business owners, and hobbyists bring their creative visions to life with print-ready artwork, custom apparel, and unmatched speed. As we continue to scale, we’re tackling complex operational challenges across physical goods, software development, new product launches, and multiple P&Ls—all while maintaining a best-in-class customer experience. We are looking for a Program Manager to help drive cross-functional execution, align priorities, and ensure that key strategic initiatives are delivered on time and with precision. Reporting to the Chief of Staff (CoS) and working closely with the CFO, this role will be instrumental in managing the intersection of operations, technology, finance, and product innovation.

As Principal Program Manager, you will be responsible for keeping teams aligned, identifying and solving roadblocks, and ensuring that cross-functional projects run efficiently. You’ll handle complex operational challenges spanning physical goods, software, new product launches, and multiple business units, all while ensuring that our organization continues to scale efficiently. This role requires a master orchestrator—someone who thrives in ambiguity, can bring order to chaos, and is energized by tackling zero-to-one initiatives that have never been done before. If you love working across multiple business functions, keeping teams accountable, and driving execution for high-impact projects, this role is for you.

Key Responsibilities:

• Manage complex programs that span e-commerce, customer support, print shop logistics, and software development.
• Work closely with supply chain, print shop partners, and engineering to improve order processing, delivery speed, and cost efficiency.
• Bridge the gap between Product, Engineering, Customer Service, Print Shop Operations, and Finance to keep teams in sync and drive execution.
• Take on projects with no playbook, designing and implementing new operational frameworks that improve efficiency and scalability.
• Develop and refine workflows that improve partner onboarding, order routing, and production efficiency within our print shop network.
• Identify pain points in the customer journey and develop initiatives to improve response times, service quality, and order fulfillment.
• Implement structured, scalable processes that reduce inefficiencies and ensure alignment across multiple business units.
• Keep leadership and stakeholders informed with clear project updates, dashboards, and performance metrics.
• Partner with the CFO to align program execution with financial objectives, ensuring cost-effectiveness and sustainable growth.
• Identify potential roadblocks and develop contingency plans to keep projects moving forward.

Qualifications:

• 5+ years of experience managing complex, cross-functional programs in e-commerce, logistics, supply chain, or high-growth tech environments.
• Strong understanding of order processing, inventory management, and logistics workflows in an e-commerce or print-on-demand setting.
• A track record of building scalable systems that reduce inefficiencies, lower costs, and improve operational performance.
• Experience launching new initiatives, building from scratch, and turning ambiguity into structured, repeatable processes.
• Strong ability to analyze KPIs, identify bottlenecks, and implement solutions that drive measurable impact.
• Comfortable working across multiple P&Ls, product teams, supply chain operations, customer service, and finance.
• Able to distill complex projects into clear action plans, ensuring all stakeholders are aligned.
• Thrives in fast-paced, ever-evolving environments where priorities shift rapidly.

Why You’ll Love Working Here:

• Opportunities to grow within the company
• Generous compensation and employer paid benefits
• Annual wellness and professional development stipend
• Perks of getting lots of clothing!