By: Chanel Frances
Jessica Holmes Holiday has stood in this exact spot before. A slab of raw concrete, stripped of walls, floors, and everything that used to make it a home. This time it happened twice in one season. Hurricanes Helene and Milton hit Anna Maria Island, Florida, back-to-back, and the flooding took her home, her 97-year-old grandmother’s home, and the office of the interior design firm she has spent 26 years building. She rebuilt all three from the ground up, and she did it without missing a single paycheck or bonus for her team.
That single fact says more about Jessica Holmes Holiday’s leadership than any mission statement could. As founder of HSH Collective, a design firm on Anna Maria Island, where she is a fourth-generation resident, she has spent her career proving that a business built on care can also last through disaster.
“We own the situation, and then I ask what the lesson is,” Jessica said, describing how she has navigated the 2008 financial crash, the pandemic, and now two hurricanes in the same year. “The thing that’s gotten me through all of it is the same: keep going, take care of your people, and figure out what you’re supposed to learn from it.”
Building an Open-Door Leadership Style at HSH Collective
Jessica started her firm at 24, with no formal business plan and no roadmap for running a growing team. “I was a pushover, the kind of boss who’d let things slide and then get resentful about it instead of actually leading,” she said. A few years ago, she began working with a positive intelligence business coach on a specific problem: how to hold real authority without losing the caring, contractor-friendly reputation she had built her whole career on.
The result is a leadership style with no office and no closed door. Jessica works from the same conference table as her team, and she describes her job less as managing people and more as making space for them. “I want to be a leader my team can come to, and I want every one of them to have a voice,” she said.
That philosophy shows up in how she has handled her own instinct to control every outcome. Jessica calls herself commanding by nature, someone who has to actively practice letting her designers make calls she might have made differently. Many of them arrived out of design school fluent in tools she never had, like advanced CAD and 3D rendering, and she has come to see the age gap on her team as a genuine collaboration between generations. Letting go of control is still the leadership skill she is most actively developing, since in her industry mistakes carry real financial and reputational weight.
Three values guide every decision Jessica makes as CEO: staying authentic to who she is as a person, delivering a genuinely great product paired with clear and professional leadership, and leading with love. “We’re all humans here; we’re a family, we support each other and lean on each other,” she said.
The Future of HSH Collective: A Lifestyle Brand in the Making
Ask Jessica where HSH Collective is headed, and the answer extends well past furniture and floor plans. Her long-term vision is a company built on a team so empowered it no longer depends on her presence in every room. Around that core business, she is building a broader lifestyle brand: a candle line for which she creates the fragrances herself, her husband’s antiques business, the couple’s growing presence at the Round Top, Texas antique show, and a memoir she has started writing about her life in the design industry.
In the nearer term, she sees three clear opportunities. The first is what she calls investment design, her formula for designing vacation rentals and investment properties, a niche she has built specifically because it gives her more freedom to take creative risks. The second is that lifestyle brand taking shape alongside the firm. The third is mentoring other female entrepreneurs, something she said tends to happen organically, through the women who gravitate toward her.
Innovation has taken practice for Jessica, and she is candid about it. She trained in an era when interior designers had to prove their professionalism before anyone would take them seriously on the construction side of a build. Watching her newer designers bring AI and 3D renderings to client presentations, and watching her team show real personality in their content, has pushed her to stay open to ideas outside her own comfort zone. She keeps current on the industry through trade partner lunch-and-learns, conferences like High Point Market, ASID’s weekly updates, and the daily education of the job site itself.
She is equally direct about the misconception she runs into most in her industry. “A lot of people, mostly men, if I’m honest, think an interior designer just picks out furniture,” she said, when the reality involves coordinating with contractors, reading construction plans, and understanding the structural details of a build from the ground up.
The Wins That Define Jessica Holmes Holiday’s Career
When Jessica reflects on her time as CEO, the hurricane rebuild tops the list, specifically that her team never missed a bonus or a paycheck through it. She also points to her very first client, a mentor who taught her early that discounting her fees meant discounting herself, a lesson she still returns to. More recently, she has taken pride in a harder decision: walking away from projects, including ones tied to old friendships, when the values did not line up, and doing it without losing sleep over it.
That same standard shapes how she runs a business responsibly. For Jessica, that means protecting client privacy, respecting the personal time of her trades and vendors by not texting after hours unless necessary, and pushing the firm toward sustainably sourced materials and lower-impact shipping within an industry that still leans maximalist and beauty-driven.
Leadership Lessons From 26 Years Running HSH Collective
Jessica’s path into leadership had no business plan behind it. “It was work hard, get yourself together, and fake it till you make it,” she said. A mentor once told her to be careful what business she built, because eventually she would have to feed it, and that warning has stayed with her for 26 years. Her other piece of advice for anyone aspiring to run a company is simpler and, to her, non-negotiable: never discount yourself. She would rather give work away for free than chronically undercharge for it.
Outside of HSH Collective, Jessica calls herself an island girl through and through, happiest on a boat with her toes in the sand. She travels often with her husband, from Round Top for his antiques business to Europe and Albania, and guards a small, tight circle of close friends, including a standing early-bird dinner over a glass of Prosecco. Between her orchid garden, Peloton, and time with her son, the same instinct that rebuilt three properties from a concrete slab is easy to spot: a refusal to let disaster decide what she builds next.
HSH Collective has rebuilt from a concrete slab and still shows up for every client on time and on budget. See their work and get in touch at hshcollective.com.
