A Journey of Change: From Corporate Retail to Belle Box Co with Jennifer O’Hare

In today’s episode of Etsy Seller Success, Dylan sits down with Jennifer O’Hare, founder of Belle Box Co., to discuss her inspiring transition from a 16-year corporate retail career to launching her own bespoke corporate gifting business. Jen’s journey offers valuable lessons for anyone considering taking the leap from a stable corporate job to entrepreneurship.

Jen’s Corporate Background and the Breaking Point

Jen spent the majority of her career at TJX Companies, a leading name in off-price retail. Over 16 years, she held roles in planning, allocation, buying, merchandising, and even supply chain management. Her career was dynamic and fulfilling, but the extensive travel—nearly half the year—began to take a toll, especially after she became a mother.

Initially, Jen believed she could balance her career with family life. However, after having her third child, the demands of corporate life felt unsustainable. The rigid structure and lack of flexibility made it clear that she needed to make a change. Over the course of three years, she and her husband discussed and planned how to transition out of her corporate role in a financially responsible way.

Making the Leap: From Idea to Business

Unlike some entrepreneurs who start with a concrete business idea, Jen’s journey began with a simple need for community and connection during the COVID-19 pandemic. She started curating thoughtful gift boxes for a small group of moms as a way to bring people together. The overwhelmingly positive response made her realize she had something special.

By the time she officially left her job in 2021, she was already considering how to scale her passion into a business. Belle Box Co. was born with the goal of elevating corporate gifting beyond the typical fruit and nut baskets.

Building Belle Box Co.: Growth and Challenges

Today, Belle Box Co. is a premium corporate gifting service that specializes in high-end, curated gift experiences for mid-sized companies and luxury brands. From employees and clients to board members and referral partners, Jen’s company helps businesses strengthen relationships through thoughtful gifting.

One of the biggest lessons Jen learned early on was the importance of pricing her products and services appropriately. As a small business owner, she realized she needed to account for all costs—including her own time—to build a sustainable business. Initially, Belle Box Co. operated out of her mother’s home, occupying multiple floors. However, as the business grew, she made the scary but necessary leap to investing in a warehouse space.

The Power of Mentorship and Adaptability

Understanding that she didn’t have all the answers, Jen sought out mentorship and business coaching early on. This helped her navigate areas she was less familiar with, such as logistics, marketing, and business structuring.

Belle Box Co. started as a direct-to-consumer business but evolved into a more personalized, service-oriented company. Jen found that she thrived on collaboration, working directly with clients to bring their gifting visions to life. This pivot allowed her to create a business that aligned not just with market demand but also with her own strengths and values.

What’s Next for Belle Box Co.?

As Belle Box Co. continues to grow, Jen is focused on expanding into on-site corporate gifting experiences, an area where she sees significant demand. She’s also looking to deepen her consulting work, advising other businesses on wholesale expansion and retail strategy.

Her advice to aspiring entrepreneurs? “Start charging for your time from day one. Understand your true cost of goods, labor, and overhead. The growth will come, and you want to be prepared for it.”

Final Thoughts

Jen’s story is a testament to the power of trusting yourself, leveraging transferable skills, and taking calculated risks. For anyone feeling stuck in a corporate job, unsure of what’s next, her journey proves that with the right planning and mindset, stepping into entrepreneurship is possible.

If you’re looking for unique corporate gifts that go beyond the standard, check out Belle Box Co. And if you’re an aspiring entrepreneur, take Jen’s advice—plan, charge what you’re worth, and trust in your ability to figure things out along the way.