Six vacation rentals do not sound like the beginning of a data business. They sound like six sets of keys, six calendars and six opportunities for somebody to ask where the Wi-Fi password has gone. In 2007, Jason Sprenkle was developing condominiums in the Florida Panhandle when an opportunity arose to manage some properties. He called his brother Jeremy. Together they founded 360 Blue with six rentals. By the end of 2013, the company was managing 237.
That small beginning is a useful place to meet Sprenkle. The later titles can obscure it: technology co-founder, software executive, board member, industry award recipient. Before the dashboards came the houses. Before the market intelligence came the ordinary, accumulating demands of accommodating guests. A holiday is wonderfully simple when somebody else has arranged it.
Across the businesses that followed, Sprenkle kept returning to that somebody else. He co-founded the guest-management app Glad to Have You, which HomeAway acquired in 2014. He then spent more than eight years leading KeyData, helping professional rental managers understand their performance. In 2026 he left the CEO job, stayed on the board and joined amenity automation company sojo as a strategic advisor. The job titles changed. The operator remained in view.
The education before the dashboard
Sprenkle's route into hospitality passed through law and real estate. He attended Florida State University College of Law from 1991 to 1994 and served as a Law Review editor. His earlier work included being a software attorney and a luxury real estate developer. It is an unusual preparation for a career spent discussing occupancy and booking patterns, though software and property would soon become recurring ingredients.
The 360 Blue story supplied a practical education of its own. Its early growth joined technology with service, two words that can coexist politely in a business plan and argue vigorously during a guest's stay. Managing a growing collection of individual homes means keeping information useful across different properties and different people. Each additional rental brings another set of details that somebody has to remember.
He helped build and lead 360 Blue for nearly 15 years before its acquisition by Natural Retreats. That operating history matters to the technology story because his experience included buying and using the kinds of tools he would later help develop. The customer was a familiar person with a familiar workload.
A small app with a very practical welcome
Glad to Have You, co-founded with Keith Landers, addressed the exchange of information between rental managers and guests. The product put property information and communication onto mobile devices. Arrival instructions, door codes and Wi-Fi passwords could travel with the visitor, rather than depend on another call to the office. Managers could stay in touch during the booking and respond to service requests.
There is a modest comedy in the product's name. Hospitality promises that it is glad to have you; the software helps the staff demonstrate it while looking after everyone else, too. The useful invention was making that welcome easier to deliver repeatedly. A guest needed the right information at the right moment, and a manager needed a manageable way to provide it.
HomeAway announced the acquisition on March 5, 2014. Sprenkle and Landers stayed on as consultants during the transition. HomeAway's financial filings later recorded approximately $16.8 million in cash consideration for the business. That is the acquisition price of the company, a distinction worth keeping clear when telling a founder's story.
The purchase placed a specialized guest tool inside a much larger vacation-rental business. It also gave Sprenkle an early example of how an operating problem could become a software product with a life beyond the company where the problem was familiar.
When the calendar needs explaining
KeyData moved the question from communicating with guests to understanding the business around them. A manager can see what is happening inside a portfolio and still struggle to judge its performance. Are bookings moving with the wider market? Is a change in revenue a local pattern? What should happen next?
The company's approach centers on reservation data obtained through direct integrations with property management systems. It gives managers ways to examine their own performance and compare it with anonymized market information. The important move is connecting the records used to operate the business with the decisions used to run it.
In April 2018, Key Data Dashboard, formerly VRM Dashboard, announced a $2.4 million Series A. The participating investors included 360 Blue and people who had backed Glad to Have You. Founder Amy Hinote stepped down to focus on VRM Intel. There was continuity in the investors and in the underlying audience: people who knew vacation rentals from the inside.
“Vacation rental managers are using our software to spend less time pulling reports and more time making informed revenue decisions.”
Jason Sprenkle, 2018
The sentence is refreshingly workaday. It does not ask anyone to fall in love with a dashboard. It asks whether the dashboard returns some hours and improves a decision. For an operator with a growing portfolio, that is a proposition that can be evaluated before the next meeting.
The numbers became a public conversation
By July 2022, KeyData had secured a $5 million credit facility to complement a $5 million Series B led by Ballast Point Ventures. Sprenkle said the company had doubled its team, revenue and customer base over the preceding twelve months. Planned uses for the capital included enterprise offerings and a larger international presence.
Growth brought a wider audience for his explanations. At the 2022 DARM conference, his sessions covered industry performance and predictive indicators, as well as setting up dashboards for individual departments. Those are related tasks: explain the larger picture, then help someone use it at a desk.
His work also reached destination organizations. At a February 2025 board meeting of Gulf Shores & Orange Beach Tourism, he presented product changes and a market update, including how shifts in inventory and supply affect commonly reported performance indicators. Board members requested changes in how the dashboard displayed data. The exchange captures something easily lost in a growth story: a useful product keeps being negotiated with the people using it.
In a February 2026 conversation with BookingsCloud's Amber Knight, he returned to the relationship between diagnosis and action. A pricing problem and a demand problem can call for different responses. Their discussion connected market intelligence with marketing execution. A chart may be beautifully drawn and still leave the manager with the next job to do.
Another enterprise, another kind of return
Alongside the commercial businesses, Sprenkle co-founded The Sonder Project with Ashley Horsley and Jeremy Sprenkle. The nonprofit's early story grew out of the 360 Blue executive team's wish to direct company resources toward people in need. The original concept included the company covering administrative expenses so donations could go toward aid.
One early partnership was with buildOn to construct schools. Volunteers, including 360 Blue employees, traveled from Santa Rosa Beach to Burkina Faso. The organization later extended its work to Malawi. Its current team page lists Sprenkle among the co-founders on its board of directors.
The name refers to the realization that other people have lives as complex and vivid as one's own. It is a generous thought to attach to an organization. It also makes a useful pause in a career usually described through acquisitions, funding and performance: there are people at the far end of every neat organizational diagram.
A handoff, with the conversation still open
In 2026, Sprenkle stepped away from KeyData's daily leadership. Dustin Downing succeeded him as CEO, while Sprenkle remained on the board. The company described the move as a planned transition after more than eight years of leadership. It was a change in responsibility within a business he had helped build.
His public reply to Downing's announcement was warm, specific and less ceremonial than such exchanges sometimes become. He praised the incoming leader's connection with the team and mission, then looked forward to “the many Miller Lites ahead.” A board transition can have a beverage clause, apparently, even when the lawyers have gone home.
The same year brought the Shortyz Pioneer Award, recognizing his contribution to the rental sector. By September 30, there was another assignment: strategic advisor to sojo, working with founder and CEO Max Farley. The company automates amenity sourcing, preparation and delivery using property and reservation information.
It is a fitting continuation. After guest communications and market benchmarks, here is another recurring piece of work inside the rental business. Sprenkle's stated interest was automation that reduces the complexity managers carry. His retirement from the CEO chair had left room for a familiar conversation about how the work actually gets done.
Return to those six homes in 2007, and the career becomes easier to follow. An opportunity to manage properties grew into an operating company. The operating experience accompanied ventures in guest software and data. Now it informs advice about the supplies that must arrive for a stay. The holiday may begin when the guest opens the door. Sprenkle's working life has repeatedly returned to everything that needs to happen before then.