Building a Business That Lasts: Hannah Ippolito on Entrepreneurship and Growth
Location: Nelson, New Zealand
Started using Squarespace: 2020
Title: Co-Founder, SquareKicker
Hannah Ippolito ventured into entrepreneurship after a career in fashion and photography. In 2020, the Circle Platinum Partner and Community Leader co-founded SquareKicker with husband and business partner Nick Ippolito. The digital storefront offers no-code design and animation tools and a marketplace for templates to Squarespace web designers.
Hannah now manages the growing 10-person team full time, and has successfully navigated the shift from hands-on creative work to strategic, long-term leadership. In this interview, she discusses her decision to keep the SquareKicker team in person, the “we’ve made it” moments that validated their hard work, and how she manages family priorities alongside a demanding startup.
What drew you to entrepreneurship, and how did that bring you to the web development industry?
I’ve always loved running businesses and been fascinated by the challenge of delivering a service in a way that genuinely delights someone. That mindset drew me to entrepreneurship long before SquareKicker existed.
Before web development, I worked in fashion design and photography. Both taught me how much I enjoy building something from scratch and shaping an experience for people.
Nick was already working in web design when the idea for SquareKicker began to form. When he shared the concept, we immediately saw the opportunity to build something exciting together. It felt aligned with our strengths and values, so we jumped in fully and committed to bringing it to life.
In what ways did your career as a photographer inform your decisions as a business owner?
Photography taught me how to balance creativity with business sustainability. In any creative career, you’re constantly holding two things in tension: producing work you’re proud of and building a business that can support your life.
That perspective helps me understand the designers we serve. They’re not just creating beautiful websites; they’re building careers. I know what it feels like to deliver creative work to clients, manage expectations, and still protect your creative energy. It shapes the decisions I make at SquareKicker, always asking whether we’re adding real value to someone’s creative business in a way that will help them thrive.
What has been the biggest adjustment you’ve faced moving from creative to leader?
The biggest adjustment has been the shift to long-term thinking. Creative work often focuses on what’s in front of you right now. Leadership requires thinking years ahead while still making wise decisions in the present.
It’s been a huge mindset shift and one that’s required a lot of learning. But it’s also been incredibly rewarding. Instead of asking, “How do I make this great?” I’m asking, “How do we build a team and culture where great work keeps happening?”
What was the “we’ve made it” moment for the business?
The first subscription payment felt surreal. Realizing that someone we didn’t know was willing to pay for what we built was an amazing moment. Another milestone came about two years in when we were able to close our web design business and take salaries from SquareKicker. That was a significant turning point.
But the moments that matter most still happen regularly. Hearing designers say they wouldn’t build a Squarespace site without SquareKicker, or that it helped them go full time in their business, those are the times it truly feels like we’ve made an impact.
What’s the best business decision you’ve made for SquareKicker?
Choosing to keep our entire team in person from day one. It was a controversial decision in the tech industry, but it has shaped our culture in a powerful way.
Being in the same space allows ideas to flow freely, helps us iterate quickly, and builds trust through everyday interactions. Walking to get coffee together or sharing lunch might seem small, but those moments strengthen relationships. I believe that closeness shows in the quality of our work and the speed at which we can produce it. It just makes work a little bit more fun!
How are you looking to evolve SquareKicker in the future?
We’re working toward a future where professional Squarespace creatives can create anything they imagine, efficiently and without compromise.
As AI continues to move quickly, I believe designers will become even more important in shaping work that feels human, distinctive, and strategic. We want to equip designers with the tools to execute ambitious ideas efficiently, while allowing space for their creativity to flourish.
How do you maintain work-life balance?
For all the working parents out there, I want to give this question a laughing emoji! I don’t think balance exists in the polished way it’s often portrayed. For me, it has been about making intentional choices for what I will prioritize.
We knew building the business would require significant focus, and we also knew raising our kids well mattered deeply. Our children are in their preteen and teen years, which is busy but such a fun season. We’ve been deliberate about making sure work never overtakes that priority.
Living in a small city with lots of outdoor options helps. Our family hikes together and spends a lot of time outdoors. I often run around sports fields while the kids are at practice which gives me a little headspace. Nick and I regularly check in to make sure the important things aren’t being pushed aside by the urgent things.
What’s your favorite part about being a Circle partner?
The community. Connecting with other designers, both online and in person at Circle Day, has been incredibly meaningful.
It’s an unusually kind and generous group of professionals. Being part of that environment keeps us close to real conversations and real needs, which makes the work we do feel collaborative and meaningful.
Key takeaways
Balance your artistic standards with business sustainability so you aren’t just delivering beautiful websites, but building a web design career that actually supports your life
Proactively manage client expectations to protect your creative energy, ensuring you can continually deliver high-quality work without burning out
If transitioning into leadership, you’ll need to shift your focus from solving immediate creative problems to building a culture where great work happens consistently
Lean into the human elements of strategy and creativity, as these will become premium assets for designers as AI tools continue to evolve
Stop chasing a perfect work-life balance and instead make intentional choices that protect your personal priorities from the urgent demands of business
Want more?
Check out Squarespace Circle, Squarespace’s program for professional designers and web design agencies. Along with exclusive content, discounts, and other perks, Circle brings professionals together from across the globe to exchange advice while connecting with new clients and collaborators.
