Director, Project Management

At Jiffy.com, we are America’s destination for print-ready artwork and unmatched speed, empowering crafters, small business owners, and hobbyists to turn their creative visions into reality. With high-quality apparel, diverse transfer types, and seamless customization, we make the process fast, efficient, and fun. As we continue our rapid growth, we are looking for a VP of Operations to drive cross-functional process excellence, cost efficiencies, and scalable operational infrastructure to support our ambitious goal of reaching $1B+ in revenue.

We’re looking for a Director of Project Management to serve as the execution backbone of Jiffy. This is a high-visibility, high-responsibility role reporting to the VP of Operations with a dotted line to the Chief of Staff. You’ll work directly with the CEO, President, and full C-suite to bring structure, urgency, and follow-through to our most important initiatives. Your job is to turn company ambition into timelines—and then protect those timelines at all costs.

Key Responsibilities

• Own the master roadmap – Build and maintain a unified, Gantt-level project view across all functions. No ambiguity.
• Spot risk early – Identify slippage before projects start. Escalate fast—with context and solutions, not chaos.
• Build visibility tools – Create dashboards, timelines, and status briefs that keep leadership informed without having to ask.
• Push for real ownership – Hold cross-functional teams (engineering, ops, creative, logistics, marketing) accountable for real, tangible deliverables.
• Drive exec alignment – Lead project syncs. Raise the red flag early. Be the one who says “this won’t ship” when no one else will.
• Deliver milestone-level execution – Track every task, dependency, and deadline. Surface blockers and drive resolution relentlessly.
• Report with precision – Flag structural risks, scope creep, and misalignment clearly to VP of Ops and Chief of Staff.

Qualifications & Skills 

• Bachelor’s in Engineering, Operations, Project Management, or similar
• PMP or Prince2 certification required
• 7–10+ years of project management or operations leadership experience in high-growth, fast-moving environments
• Proven track record launching 10+ cross-functional initiatives with zero timeline slippage
• Experience implementing project planning frameworks in organizations that didn’t have them
• Experience in high-growth DTC brands, ideally with exposure to supply chain and operational complexity
• Background in enterprise-level product or operations teams with direct accountability for shipping and delivery
• Experience in e-commerce infrastructure or platforms where project timing is critical to success
• Consulting experience at firms like McKinsey or BCG is acceptable—only if followed by hands-on leadership in an operating role
• Detail-obsessed – You don’t miss edge cases. You sniff out scope gaps before they become issues.
• Milestone absolutist – Nothing lives in the abstract. You assign owners, define dependencies, and track to real deadlines.
• Risk radar always on – You catch soft briefs, fake scopes, and phantom timelines before they derail anything.
• Escalation fluent – You push up, across, or down when needed—but always with data, control, and optionality.

Why Join Jiffy?

• Fully remote with occasional meetings in the Whitby office
• Opportunities to grow within the company
• Competitive compensation and employer-paid benefit
• Wellness & Professional Development annual stipend
• Supportive team with proven results
• Perks of getting lots of clothing!