Director, Project Management

Summary

Join Jiffy.com, America’s premier destination for print-ready artwork, as their new Director of Project Management. This high-visibility role reports to the VP of Operations and the Chief of Staff, requiring direct collaboration with the C-suite to translate company ambitions into actionable timelines. You will be responsible for building and maintaining a unified project roadmap, identifying and mitigating risks, developing visibility tools, and holding cross-functional teams accountable for deliverables. Success in this position demands meticulous attention to detail, a proactive approach to risk management, and the ability to effectively escalate issues with data-driven solutions. Jiffy offers a fully remote work environment with occasional office meetings, opportunities for growth, competitive compensation, and various benefits.

Requirements

• 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

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

Preferred Qualifications

• 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

Benefits

• 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!