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.
Jiffy Shirts is currently on a mission to fundamentally disrupt the stagnant, multi-billion-dollar custom apparel industry. We are an AI-first company building the future of on-demand manufacturing and e-commerce. We have a profitable, fast-growing business, and we are reinvesting to build a future where fashion is instant, personal, and created by everyone.
We operate with a wartime mentality. Our culture is defined by speed, extreme ownership, and a relentless refusal to be blocked. We are not looking for someone who wants a comfortable 9-to-5. We are looking for operators who want to get in the fight, aggressively take on the market, and build something legendary.
Requirements
**Basic Qualifications**
- You currently reside in Chicago and possess intimate, first-hand knowledge of its distinct neighborhoods, cultural hubs, economic arteries, and university ecosystems. This is a non-negotiable.
- You have a proven track record (5+ years) of launching and scaling local, field, or community marketing campaigns from the ground up, with specific demonstrable success in an urban market.
- You will be a real-world embodiment of a Jiffy Operator:
- Extreme Ownership: You see CHI market share, P&L, and team performance as a direct reflection of your leadership. There are no excuses.
- Extreme Bias for Action: You are a doer, not a delegator. You are uncomfortable with meetings that don't end in immediate next steps.
- Relentless Tenacity: You have a history of running through walls to achieve a goal. Problems are opportunities, not blockers.
- You are Data Zealot. You have deep experience managing a budget, setting and tracking KPIs for multi-channel campaigns (both online and offline), and holding yourself and your team accountable to ROI, CAC, and LTV.
- You are a proven leader and recruiter. You have experience hiring, training, and managing a distributed team of high-performing field operators or community managers.
- You have direct, hands-on experience with scrappy, guerrilla marketing tactics. You've run campus activations, launched dorm blitzes, negotiated local partnerships, and executed event hijacks yourself.
- You are proficient with hyper-local digital channels, including geo-targeted social media campaigns (Meta), Google My Business/Yelp optimization, and local SEM.
- You have experience thriving in a high-growth, ambiguous, and resource-constrained startup environment. You know how to make a dollar do the work of ten.
- You have strong negotiation skills for securing partnerships with everyone from university clubs to local business owners.
**Preferred Qualifications**
- You have an existing network within the Los Angeles small business, university, or creative communities.
- You have experience in the apparel, e-commerce, creator economy, or CPG space.
- You have a personal passion for AI, design, and leveraging new technology to solve old problems.
**This role is not a fit for you if...**
- This role WON'T have a large, established team or unlimited resources. You must be a builder and a doer from day one.
- This role WON'T have a slow, predictable 9-to-5 schedule. The mission requires operating with urgency at all times.
- This role WON'T be a fit for someone who needs perfect data or a rigid process to make decisions. You must thrive in controlled chaos.
- This role WON'T be for a pure strategist; you must be willing and eager to execute tactics on the ground yourself to lead your team by example.
**Location: **Remote within the Chicago area - (may require travel as needed)