Feature | By Jocklyn Mundy | Main Photo by Michael Kleinfelt • Windermere Photography | Interior Photos by Valerio Di Domenica
Some journeys aren’t gentle; they stretch, demand resilience, and require strength. But over time, those experiences cultivate something grounded and steady, ready to take root in good soil.
Arjun and Sara Kumar have one of those stories.
Though Windermere is still getting to know them, their presence already feels familiar, genuine, kind, and quietly confident. There’s a steadiness about them, shaped by experience. Conversations with them are thoughtful and sincere. They value meaningful time with others and authentic relationships.
Parallel Lives, One Beginning
Before Florida Sunshine, their story began far north in the suburbs just outside Toronto, where snow framed childhood winters and where two separate lives would one day grow together.
Although they grew up 5 miles apart, they first met in high school at a local gym, where Sara worked at the front desk, and Arjun worked out during his lunch breaks.
Years passed, and Sara left for college. Arjun continued his education and training in the medical field. Sara returned home after graduating with a degree in kinesiology and messaged Arjun to ask whether his father, a cardiologist, might be hiring. He was, and soon the two found themselves working alongside each other in a clinical setting, with Arjun performing cardiac imaging and testing and Sara assisting with patient preparation, vitals, and stress-testing protocols.
A Different Calling
In a family where the natural next step was medical school, Arjun was expected to follow the familiar route. Yet even as a child, another pattern was forming: he was the one called in when the computers failed, the printer jammed, or the system froze. It wasn’t the traditional path his family imagined, but it was the beginning of the one meant for him.
Working in the clinic gave Arjun a front-row view of what physicians were up against: systems that were necessary but hard to navigate, and nearly nonexistent support. For years, he watched technology complicate workflows rather than improve them. When software malfunctioned or updates caused disruption, there was no one to call, no real human support behind the system. Doctors were left waiting, patients were delayed, and the frustration became familiar background noise in the healthcare setting. Arjun explains, "It wasn’t that the technology was bad; it was that no one was standing behind it."
Arjun saw an opportunity hidden in plain sight: physicians didn’t just need software, they needed a partnership. They needed someone who understood the realities of patient care and the support required to back it up. That realization became the spark.
Arjun understood the clinical workflow and technology, but more importantly, he understood people. That combination became the foundation for what would come next: an early version of a service model that prioritized responsiveness, reliability, and respect.
Arjun first laid out the vision to his father, not as a polished business plan but as a possibility. A better way. A system where physicians felt supported rather than abandoned by the technology designed to help them. His father understood immediately. He had lived the frustrations firsthand, and he saw not only the need but also Arjun’s ability to meet it.
Building Something Together
Nearly fifteen years ago, with that vision in mind, Arjun founded a healthcare technology company built around a simple but revolutionary principle: put the customer first. It sounds basic, almost old-fashioned, but in a field dominated by automated responses, long wait times, and cold transactional exchanges, that human approach set his company apart almost immediately.
It was Arjun’s father who suggested that Sara step into the new company. She already understood the clinical environment, the patient flow, and the demands placed on physicians and staff. More importantly, she had the steadiness and capability to help build something that required both trust and precision. From the beginning, it was simply Arjun and Sara together; they shaped the company's earliest framework. They handled what needed to be done, side by side, building something real, one decision, one late night, one solved problem at a time.
Sara’s “temporary help” became a full-time partnership as the business grew. By 2019, the work had outgrown its beginnings. What started with just the two of them sharing responsibility evolved into a multi-location operation, with a main team in the Toronto area and additional offices supporting U.S. operations in San Francisco and Atlanta. It was steady growth, born from results.
A Wedding and a Turning Point
Over time, Arjun and Sara’s partnership, which began in shared work, became a shared life, not marked by a single moment, but by thousands of small ones: trust, respect, and choosing the same direction again and again.
Arjun proposed to Sara in early fall in Asolo, a small, quiet town north of Venice, on a balcony overlooking vineyards across the hills of the Prosecco region.
While planning their wedding, an unexpected opportunity appeared. They weren’t seeking investors, and going public wasn’t on their immediate horizon, yet timing has a way of arriving before we do. They were approached with a single proposal: merge the company and take it public in one coordinated step. As Arjun put it, “We merged and went public in one shot.”
With that chapter underway, they returned their focus to the one already waiting: a vineyard in Italy, the setting where they would say their vows. They packed for their wedding, boarded a plane, and allowed themselves to step fully into a moment that was theirs alone.
They married just outside Verona, at a historic vineyard credited with the creation of Amarone, a rich, full-bodied red wine distinctive to the region. The setting was timeless, tucked between vines, stone buildings, and a small pond beside what the owners fondly called their “coffee house.” It wasn’t extravagant; it was intimate and meaningful. The owner’s wife stepped in as a wedding planner, ensuring every detail felt personal. It was a celebration rooted in connection, the perfect reflection of who they were then and who they were becoming.
A Season of Growth
There was no honeymoon. The timing of the business and the demands awaiting them meant that celebration quickly gave way to responsibility. On the month of their wedding, the company went public. Instead of taking time off to celebrate, they navigated the demands of rapid growth, guiding the organization as it expanded into a multi-billion-dollar enterprise with more than 5,000 employees across Canada and the United States within three years.
When the pandemic struck, the demands intensified. As a healthcare software provider, the company became central to the urgent need for virtual care infrastructure, requiring nonstop work, seven days a week, with many overnighters. The growth was staggering, the pace unrelenting, and yet there was a deep sense of responsibility woven through every decision. They knew the work mattered, and that it was helping physicians care for patients during one of the most uncertain chapters in modern healthcare.
Amid the demanding 2021 season, they welcomed their daughter, Solaia. Her name was chosen for its Italian roots, subtle Indian resonance, and its meaning: a place touched by the sun’s energy. Her middle name, Ruby, carried its own significance, echoing the internal code name of a pivotal company acquisition and, fittingly, her birthstone.
Choosing Family, Climate, and a New Pace
The combination of parenthood and long Canadian winters during a global pandemic made the longing for a warmer climate and a more balanced life impossible to ignore. Remote work made relocating possible, but it was more than logistics. It was a realization: it was time for space to breathe, grow, and build a season defined by family, not deadlines.
Florida may have first appeared in conversation as a climate shift, but the connection ran deeper. Orlando wasn’t unfamiliar; it was woven into Arjun’s childhood. Three decades earlier, his grandfather had secured major contracts to supply and install windows for Universal CityWalk and the Orange County Convention Center, work that brought the family to Central Florida regularly. The familiarity felt like the next rightful chapter.
Finding Windermere
They chose Dr. Phillips first, with all of the conveniences within minutes. For a season, it worked. But convenience, they realized, is different from connection. The fast pace of Sand Lake Road offered access, but not belonging. By chance, they found Windermere, Arjun recalls, “When we hit the roundabout at 6th, we knew we wanted to make this home.”
Finding a home in the Town of Windermere proved more challenging than anticipated. Offers were written, hopes rose, but the market moved quickly, homes sold before they ever hit the public eye, and timing seemed consistently just out of reach. Yet even through the disappointments, the feeling never changed; they knew Windermere was where they were meant to land.
As their search area broadened, they found a home in Keene’s Pointe, one with history, warmth, and a lived-in sense of life. The previous family had raised their children there from the youngest school days all the way through college. The home had seen milestones, celebrations, the kind of stories that leave a gentle imprint even after the furniture is gone. Stepping inside didn’t feel like entering a house.
It felt like continuing a chapter someone had begun with care.
Arjun and Sara have an annual tradition of watching their wedding video on their anniversary. Solaia, naturally, became part of that tradition. With the sincerity only a child can offer, she asked why she hadn’t been invited to the wedding. Arjun and Sara laughed, explaining gently that she hadn’t been born yet. The question lingered: to her, the memory didn’t feel complete. With her sweet insistence, they returned to Italy and recreated a handful of their favorite wedding portraits, this time with Solaia beside them. She wore a miniature version of Sara’s bridesmaid look, beaming with joy at being a part of the fairytale. One day, she will realize she was always a part. Those images now sit alongside the originals. Not replacing them, completing them.
A Deepening Passion
Over time, as life steadied and rhythm returned, another thread of their story began to surface, one that had been present long before Florida, long before the move, long before they ever imagined stepping into entrepreneurship again: a growing appreciation for wine, its craftsmanship, and the culture surrounding it.
Arjun and Sara have always loved traveling, with Europe often topping the list. In those early years, their taste was straightforward: beer and wings, shared at the end of long workdays. But as life moved forward, their interests evolved, and a small personal shift became the catalyst. When Arjun removed gluten from his diet, beer disappeared, and wine took its place. What began as a substitution quickly became a fascination.
Arjun reflects, “Wine wasn’t like anything else. It wasn’t fixed. It wasn’t singular. You could spend a lifetime studying it and still never reach the end. There was always another region, another soil, another technique, shaped by the hands and heart of the people who made it.”
The more they learned, the more meaningful it became, not just to drink, but to understand. Wine carried more than flavor. It held history, craftsmanship, and generations of knowledge.
As their interest deepened, so did their awareness of the culture that often surrounded wine, one that didn’t always match the heart behind it. Arjun said it plainly: “One of the things that frustrated me the most was how unwelcoming the wine world could feel. If you didn’t already know, you were treated like you didn’t belong, or pushed toward whatever the restaurant needed to sell, rather than what actually fit your taste. It felt strange that something rooted in history, family, and human connection could feel like a status test.”
Winery visits were no longer sightseeing; they were immersion. Conversations with sommeliers turned into lessons. They sought out vineyards where the owners still walked the rows, where the winemaker’s fingerprint, not a corporation, guided every bottle.
It wasn’t about collecting wine; it was about connecting to the story within it. And what surprised them most wasn’t the complexity; it was the humanity. Wine wasn’t transactional. It was relational. Shared. Experienced.
In that way, it echoed their first business: built not on product, but on people. Over time, curiosity became intention. They found themselves teaching friends and family what they were learning; pairing food thoughtfully, explaining how flavor shifts with context, and inviting others into the experience, not as observers, but as participants.
There is a moment when an interest becomes a calling, when sharing it feels as meaningful as experiencing it. For Arjun and Sara, wine became exactly that.
Where Passion Found Its Home
As life in Windermere settled, another transition was already underway. Their chapter with WELL Health Technologies was drawing to a close, with their final separation set for 2024. For many, that moment might have signaled a time to pause after years of demanding work, yet that wasn’t the path The Kumars were wired for. Instead, they found themselves exploring a new possibility: sharing their love of wine, ideally in the town that they loved.
When Arjun learned that the corner of 6th and Main was slated for development, the decision was instant. There were no spreadsheets, he simply knew. Sara recalls, "That corner felt right." Windermere had given them a community and a sense of place. Wine had given them purpose. And Solvino became the natural expression of both.
Starting another business wasn’t a necessity; it was a calling. They wanted to build something meaningful in the community where they would raise their children, something rooted in passion, not pressure. And anyone who knows Arjun understands: stillness has never suited him. Sara laughs softly and says, “He’s not someone who idles.”
Still Growing
As the Kumars continue to settle, they are getting to know Windermere the same way most families do, one conversation, one connection at a time.
Their daughter, Solaia, is in PK4 at Windermere Prep. She is quite the conversationalist, greets new people with confidence, and seems to absorb the world with equal parts wonder and certainty. Sara says, “Watching her flourish here has been one of the great joys of this season.”
Their story, like all meaningful ones, is still unfolding. As a family, they’ve welcomed opportunities to connect locally, supporting events such as Run Among the Lakes and partnering with Pistil for November’s holiday open house. Arjun shares, “Being part of a community means participating and commitment, we don’t want to just live and work here, we want to contribute to what makes Windermere special.” Sara agrees, "Home isn’t just where you live, it’s where you settle into belonging.”
There are always transitions to navigate when stepping into a close-knit community, rhythms to learn, traditions to embrace, and relationships that take time. Arjun and Sara carry those realities with grace and patience. They don’t dwell on past challenges or hurdles along the way; instead, they continue forward with steadiness, humility, and sincerity.
Windermere is a special place, where stories aren’t rushed, where belonging forms slowly and meaningfully through shared life. And now, with roots planted, Arjun, Sara, and Solaia continue to grow in the next chapter, not hurried, not forced, but naturally as it’s meant to.
Their story in Windermere is just beginning, shaped by gratitude for the place they now call home.
