Director, Project Management

Jiffy.com; United States; Remote; USD 130,000 - 230,000; Full time

Job summary

Jiffy.com is seeking a Director of Project Management, a key role that will drive project execution and ensure alignment across the organization. With responsibilities including managing the master roadmap and ensuring accountability across functions, the ideal candidate will bring extensive project management expertise and a proactive risk management approach. This position offers remote work flexibility and is crucial for supporting Jiffy.com's ambitious growth objectives.

Benefits

Fully remote with occasional meetings

Opportunities for growth

Competitive compensation

Wellness & Professional Development stipends

Supportive team

Clothing perks

Qualifications

• 7-10+ years of project management experience.
• Proven track record launching initiatives with zero timeline slippage.
• Deep understanding of eComm, DTC, SaaS, or supply chain operations preferred.

Responsibilities

• Own the master roadmap and maintain a unified project view.
• Identify risks early and escalate with context and solutions.
• Drive executive alignment and hold teams accountable for deliverables.

Skills

Project management

Operations leadership

Risk management

Cross-functional collaboration

Education

Bachelor's degree

PMP certification

MBA or MEng

Job description

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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
  
  
  

Requirements

Qualifications & Skills

• 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
• Deep understanding of eComm, DTC, SaaS, or supply chain operations preferred
• Bachelor's degree required; PMP or Prince2 certification required; MBA or MEng a plus
• 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

Why Join Jiffy?

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

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Other

• Industries

  IT Services and IT Consulting

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