VP of Engineering

We’re Jiffy. We launched over a decade ago with a simple mission: use tech to combine an unparalleled level of customer service with the fastest delivery in the blank apparel, direct-to-film transfer, and custom apparel industries.

We’re more than a T-Shirt company; we’re a support system for the creator + creator economy, home hobbyist, the small business owner, and more. Today, we help millions of small businesses build their vision from scratch. And we’re hiring!

We’re searching for a hands-on, deeply technical VP of Engineering — a true hacker at heart who can think big about architecture, scale, and the systems behind a high-volume transactional business, while leading and inspiring a growing engineering organization.

This role is for someone who’s happiest building and shipping, not writing PRFAQs or spending their day in meetings. You’ll lead Jiffy’s technical strategy, scale our platforms, and mentor a team that solves challenging e-commerce, logistics, and custom manufacturing problems. You’ll work closely with Product, Marketing, and Operations but keep a clear builder’s mindset — pragmatic, hungry, and focused on delivering impact fast.

What You Will Accomplish

• Own and evolve Jiffy’s technology roadmap — from infrastructure to architecture to shipping  
• impactful products.
• Build and scale the engineering team: hire, coach, and performance-manage a team that values speed, quality, and customer impact.
• Mentor technical leaders while staying close enough to the work to guide system-level decisions and unblock teams.
• Collaborate cross-functionally with Product, Marketing, and Operations to align technology with business outcomes — and translate complex tech strategy into clear, customer-focused goals.
• Lead architecture for high-volume, transactional systems powering e-commerce, logistics, and custom manufacturing.
• Ship fast and iterate — prioritizing pragmatism and delivery while maintaining technical excellence.
• Evaluate and adopt technology thoughtfully — focusing on what drives performance and scale, not chasing hype.
• Ensure security, scalability, and reliability across platforms and infrastructure.
• Drive a high-performance culture that embraces accountability and doesn’t tolerate underperformance.

Basic Qualifications

• 8 - 12+ years of progressive engineering experience, including at least 3+ years leading teams at a senior level (VP, Head of Engineering, or founding engineer scaling a team).
• Bachelors Degree in Computer Science
• Hacker mindset: you’ve built and shipped complex systems, can dive deep when needed, and love solving hard problems.
• Experience with high-volume transactional systems, e-commerce platforms, logistics, or custom manufacturing.
• Pragmatic leader: you balance vision with execution, can say “no” to distractions, and ship fast while keeping quality.
• Cross-functional collaborator who can engage with Product and Marketing at a strategic level but stays technical.
• Effective people manager who sets a high bar, addresses underperformance, and scales a strong engineering culture.
• AI/ML expertise or hands-on experience integrating AI into products is a plus.
• Experience with mobile apps is nice-to-have (but not required).
• Not focused on academic publications — you’re about solving real-world problems.

Preferred Qualifications

• Advanced degree in Computer Science or mathematics — or equivalent deep technical expertise.
• Our tech Stack: AWS-hosted platform - Ruby on Rails - Vercel / Angular - Rust and Python

Why You’ll Love Working at Jiffy

• Impact at scale — millions of small businesses depend on what you build.
• Room to shape the future — own architecture, systems, and team culture.
• A hacker-friendly environment — where pragmatism, speed, and building the right thing matter more than buzzwords.
• Opportunity to double the engineering team and influence the next era of Jiffy’s growth

• Compensation & Growth: Competitive salary, equity opportunities, and performance-based bonuses.

• Comprehensive Benefits: Full medical, dental, and vision coverage, with a portion of premiums paid by Jiffy.
• Retirement Planning: 401(k)
• Wellness Support: Annual wellness benefits to help you stay healthy and balanced.
• Tools for Success: Choice of MacBook or PC laptop, plus equipment for your home office setup.
• Perks & Extras: Annual credit of $200 to use on our website plus more team merch drops than you will know what to do with!
• Professional Development: Annual stipend to support your learning and career growth.

Compensation: Base 350k+, Bonus, Equity

• EEO - Jiffy is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristics. Jiffy considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Jiffy is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures.