Director, Project Management

Jiffyshirts; United States; Remote; USD 120,000 - 170,000; Full time

Job summary

Jiffyshirts seeks a Director of Project Management to facilitate high-impact initiatives and align timelines with executive leadership. This fully remote role offers a competitive salary and an opportunity for growth within a fast-paced, high-growth company. The successful candidate will have a proven track record in project management, with experience in direct-to-consumer brands and strong leadership skills.

Benefits

Opportunities to grow within the company

Competitive compensation and employer-paid benefits

Wellness & Professional Development annual stipend

Supportive team with proven results

Perks of getting lots of clothing!

Qualifications

• 7–10+ years of project management or operations leadership experience.
• PMP or Prince2 certification required.
• Experience in high-growth DTC brands with supply chain exposure.

Responsibilities

• Own the master roadmap and build a unified project view.
• Identify risks early and escalate quickly.
• Lead project syncs and ensure alignment across teams.

Skills

Project Management

Leadership

Risk Management

Operations

Analytical Skills

Communication

Education

Bachelor’s in Engineering, Operations, Project Management, or similar

Job description

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!