Pop-up Sales Associate
Boost your chances before you apply.
Life is Good
Boston, MA, US
Summary
Engage with customers to provide a positive brand experience and drive sales through personalized product creation. Operate heat press equipment to customize hats and t-shirts while maintaining the cleanliness and organization of the pop-up cart.
Job Description
Bring Optimism to Boston's Most Iconic Marketplace
Love meeting new people? Thrive in a fast-paced environment where every conversation can turn into a sale? Join Life is Good at our Faneuil Hall pop-up, where you'll help create custom hats and t-shirts, connect with visitors from around the world, and spread the power of optimism one interaction at a time. Whether you're a DIY enthusiast, a maker at heart, or simply love creating something unique with your own hands, you'll enjoy bringing each customer's personalized hat or t-shirt to life. If you're outgoing, motivated by results, and energized by making someone's day a little better, we'd love to meet you.
Earn $20/hour plus 5% commission on sales while creating memorable customer experiences in the heart of Boston.
Why This Job Exists
Faneuil Hall has drawn people together since 1742. Life is Good is setting up there, and this role exists to make sure every person who walks by our cart has a chance to walk away with something that makes their day — a custom hat, a t-shirt, or just a conversation that sticks. You are the live, in-person expression of a brand built on the belief that optimism is a force for good. Your job is to make that impossible to ignore.
IMPORTANT DETAILS
- This application requires a significant commitment to answering specific questions. You may want to compose your answers outside of this app and paste them once you're satisfied with your composition, spelling, grammar, and tone. We can't consider incomplete applications.
- This role is based on-site at our Faneuil Hall pop-up location in Boston, MA. Typical shifts are either 10:00 AM–3:30 PM or 3:30 PM–9:00 PM. Candidates should have flexibility to work a variety of shifts, including evenings and weekends.
- Compensation: $20/hour plus 5% commission on sales.
- Everyone who applies will get a response from a human. Although we love and use AI regularly, you're about to put a lot of heart and skill into this application and deserve a human response. You'll get one. If you don't answer the questions or meet the requirements below, you'll get a swift and kind rejection.
What You Know and Have Done
- You have experience in a customer-facing role — retail, hospitality, events, or anywhere you had to win people over quickly.
- You are comfortable and confident talking to strangers and thrive in high-foot-traffic environments.
- You are available for weekend shifts and have flexibility across the week.
- You have operated or are willing to learn hands-on equipment (heat press training is fully provided).
What You’ll Do
- You engage customers at the cart with warmth and genuine product knowledge — meeting them where they are, not running a script.
- You operate the hat and shirt heat press to create custom, on-demand pieces on the spot.
- You drive sales through authentic connection, turning curiosity into conviction and passersby into fans.
- You keep the cart looking sharp, stocked, and running smoothly every shift.
- You represent Life is Good’s mission to every person you meet — tourist, local, skeptic, or true believer.
- You use AI tools to quickly get up to speed on product stories, brand history, and customer FAQs — so you can answer questions confidently and keep the conversation moving.
Curious what the job looks like? Click HERE to watch the heat press in action and see how you'll create custom t-shirts for customers.
How You Show Up
- You bring energy that makes the cart a destination, not just a display.
- You take pride in the craft — a clean press, a great recommendation, a moment that turns a passerby into a fan.
- You take ownership of your space and your shift without being asked.
- You stay motivated by results and take genuine satisfaction in the win.
- You know and understand the impact of our mission and the Life is Good Superpowers.
- You are skilled and comfortable working independently and as part of a team.
- You give and receive feedback thoughtfully and constructively.
- You are known for having a positive impact on those around you.
When You Know You’re Successful
- You consistently hit your sales targets and earn commission every shift.
- Customers leave the cart in a better mood than when they arrived.
- The cart runs without friction — equipment is clean, product is ready, and you’re set up before the first person walks by.
- People who stopped out of curiosity leave as Life is Good fans.
#LI-DNI
For five years, Bert and John Jacobs drove up and down the East Coast, selling their t-shirt designs on the streets and in college dorms. They slept in their van, lived on PB&J, and showered when they could. The adventure was great, but sales were, uh, lacking.
In 1994, with just $78 to their names, Bert and John designed their first “Life is Good” t-shirt to counter the negative news – and discovered how those three simple words could inspire people to focus on the good.
It should have come as no surprise that the power of that one idea was just too strong to get wrong. After all, Bert and John’s mom, Joan Jacobs, had raised them to believe in the power of positivity.
As a parent of six kids, raising the family on their dad’s slim salary, Joan still managed to make little moments magical. She didn't just tell bedtime stories. She unlocked her kids’ imaginations. In her tales, she became a wolf on a bicycle, or a princess in a flying submarine, or a dragon who breathes love instead of fire. In fact, our logo was inspired by Joan’s creative bedtime stories. It’s a symbol of her fierce love and a tribute to her playful imagination.
We like to think of Joan Jacobs as the original “Playmaker,” a term we coined that describes those who help kids heal and thrive through the power of play. In Joan’s honor, more than 10% of Life is Good’s annual net profits are donated to the Life is Good Playmaker Project to help raise the next generation of optimists.
Founded
1994
Company size
51-200 employees
Industry
Retail Apparel and Fashion
Org type
Privately Held
Headquarters
Boston, Massachusetts
For five years, Bert and John Jacobs drove up and down the East Coast, selling their t-shirt designs on the streets and in college dorms. They slept in their van, lived on PB&J, and showered when they could. The adventure was great, but sales were, uh, lacking.
In 1994, with just $78 to their names, Bert and John designed their first “Life is Good” t-shirt to counter the negative news – and discovered how those three simple words could inspire people to focus on the good.
It should have come as no surprise that the power of that one idea was just too strong to get wrong. After all, Bert and John’s mom, Joan Jacobs, had raised them to believe in the power of positivity.
As a parent of six kids, raising the family on their dad’s slim salary, Joan still managed to make little moments magical. She didn't just tell bedtime stories. She unlocked her kids’ imaginations. In her tales, she became a wolf on a bicycle, or a princess in a flying submarine, or a dragon who breathes love instead of fire. In fact, our logo was inspired by Joan’s creative bedtime stories. It’s a symbol of her fierce love and a tribute to her playful imagination.
We like to think of Joan Jacobs as the original “Playmaker,” a term we coined that describes those who help kids heal and thrive through the power of play. In Joan’s honor, more than 10% of Life is Good’s annual net profits are donated to the Life is Good Playmaker Project to help raise the next generation of optimists.
Founded
1994
Company size
51-200 employees
Industry
Retail Apparel and Fashion
Org type
Privately Held
Headquarters
Boston, Massachusetts
