Every great brand has a heartbeat you can feel… and a nervous system you don’t see.
Ours runs on connection, creativity, and a whole lot of behind-the-scenes brilliance.
We’re looking for a Vice President of Innovative Technology who doesn’t just keep the lights on, but understands how the whole house hums. Someone who sees technology not as a support function, but as a force multiplier for optimism, growth, and smarter ways of working.
This role is part strategist, part translator, part builder… and part explorer of what’s possible. You’ll help us thoughtfully weave AI into the way we work, not as a buzzword, but as a practical teammate, automating the repetitive, accelerating insight, and giving our people more space to do the work that actually matters.
You’ll turn complexity into clarity. You’ll make systems talk to each other (nicely). You’ll help our teams spend less time wrestling with tools and more time creating, connecting, and contributing in meaningful ways.
You’re the kind of person who can zoom out to see the big picture, then zoom all the way in to fix what’s slowing us down. Curious about AI. Grounded in reality. Optimistic about what humans can do when technology does its part.
Here, we believe optimism is a choice, and great technology is how we scale it.
After years of steady leadership, our current VP of IT is retiring, leaving behind a strong foundation and a team ready for what’s next. This isn’t a rebuild, it’s a handoff. A chance to step into something solid and help shape where it goes from here.
Got you curious?
IMPORTANT DETAILS
Pay Transparency:
We post our jobs on a collection of sites. Not all of them portray accurate information about our compensation ranges. For years, we've used a market-based approach to determine starting pay for all roles at Life is Good. We encourage you to explore reputable salary calculators like Salary.com or PayScale and, using accurate data for the apparel industry, this job (from the job description), our company size (under 300 people), location (Boston), and the required experience for this role (10 years or less), you will see the pay range for this role.
Requirements
Now let's get to the job!
YOUR OBJECTIVE
You lead the vision, management, and execution of the Life is Good technology ecosystem and build an IT foundation that is secure, scalable, and ready for what’s next. You ensure technology doesn’t just support the business—it moves in sync with it, translating company goals into systems that enable speed, security, clarity, and growth. You are a champion of AI adoption, identifying opportunities to automate, augment, and accelerate work across the organization.
YOUR JOB
Lead SAP Strategy and Execution
Lead a High-Performing IT Team
Champion AI Adoption and Intelligent Automation
Own Security and Risk
HOW YOU SHOW UP
WHEN YOU'LL KNOW IT'S WORKING
Benefits
Our community is full of green space, outstanding food, and entertainment options.
We’re located in beautiful, scenic Hudson, New Hampshire, where we've built a brand new headquarters. We offer an on-site gym with showers, top quality Medical, Dental, Vision, Flexible Spending Accounts, Life, AD&D, Short and Long-Term Disability, 401(k) with a match, Paid Time Off (PTO), 10 paid holidays, Good Vibes Time (we pay you to volunteer for the non-profit cause of your choice) and Family Time. You’ll be involved in growing our social mission through the Playmaker Project.
Life is Good is an equal opportunity employer and does not discriminate against otherwise qualified applicants on the basis of race, color, religion, national origin, ancestry, sex, age, mental or physical disability, pregnancy, sexual orientation, gender orientation, or expression, marital status or veteran status, or any other legally protected characteristic under applicable federal or state law.
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.
