Jason Tillery and the Value of Doing the Boring Work

Before Jason Tillery helped turn property marketing into software, he and Vishu Ramanathan agreed to do a broker’s marketing work themselves. The offer was $100 a month. Brochures, emails, website updates: the founders took on the chores and learned the sequence. An industry built around expensive buildings had presented them with a modestly priced education.

There is a pleasing lack of ceremony in that beginning. No customer needed to imagine a distant future. Someone had materials to prepare, and two developers were willing to prepare them. The question of what to automate could wait until they understood what kept happening. A brochure can be a surprisingly effective business plan if you have to make enough of them.

A hundred dollars’ worth of homework

Tillery and Ramanathan had been consulting while trying to develop products of their own. Their consumer ideas struggled; business clients continued to pay. They began looking for a business problem with a customer attached, talking to people in bars and cafes about the frustrations of their working lives. Commercial real estate supplied an opening.

The manual work mattered because it put the founders inside a process. A property’s details had to travel into several different materials. Each new destination brought another opportunity to copy, revise, or forget something. Doing the job exposed the repetition. Software eventually followed, carrying information through tasks the developers had already performed themselves.

By the time of Buildout’s 2017 funding announcement, that experiment had become a platform used by more than 1,600 brokerages and over 10,000 users across all 50 states. The company raised an $8 million Series A. Those figures describe the distance traveled; the early service arrangement explains the route. Tillery’s contribution began with learning an unfamiliar profession closely enough to build for it.

The refresh button, and other small enemies

A smaller piece of software offers another view of the partnership. Tillery and Ramanathan co-authored Pushify, an open-source tool that lets changes to CSS appear in browsers without a manual refresh. Its premise is almost comically specific. Edit a style sheet; see the result. Repeat across browsers without repeatedly reaching for the same button.

That project belongs beside the brokerage story because both concern interruptions that are easy to accept as part of the job. Refreshing a browser is hardly an ordeal. Neither is entering one property detail twice. At sufficient frequency, however, little tasks acquire a considerable appetite. A developer who notices them has plenty to work on before inventing an entirely new behavior.

Tillery’s GitHub profile also lists Rio, described as a JavaScript framework for real-time web applications on Rails. These public projects give the executive biography a useful texture: software made at the level of the working interface, where a user waits, repeats an action, or hopes something will update.

At Buildout, Tillery initially wrote the code while also dealing with bills and the office. Later, as CTO, he described trying to preserve time for programming even as a growing team changed his responsibilities. His affection for the craft was plain: “It really is the one thing that I truly love doing.”

His account of choosing between React and Vue was equally practical. An engineer built an interface in both, giving the team actual code to compare. A framework debate had been turned into something colleagues could inspect. For anyone who has sat through a meeting composed entirely of preferences, this sounds almost indecently useful.

A spreadsheet earns its keep

One later product makes the underlying problem particularly easy to see. Buildout Grids connected spreadsheet work with data stored in Buildout. Brokers could prepare rent rolls, underwriting models, and comparison charts, then pass spreadsheet information into branded marketing documents through an integration with Buildout Docs.

The spreadsheet survived. What changed was the distance between it and the rest of the job. A calculation in one place could become information in a proposal or brochure without requiring the same amount of manual handling. The usefulness lay in the connection, a detail that rarely gets its own glamorous product photograph.

By the 2023 Building CRE report, the business Tillery co-led described a suite spanning prospecting, data management, CRM, visual media, and commissions. A founder who began with marketing chores was now involved in software touching more of a brokerage’s day. That expansion also enlarged the organizational task: different products, different teams, and more decisions about how they should work together.

The meeting nobody scheduled

Tillery’s career at Buildout included a departure and a return. Following a private equity investment in 2020, both founders stepped away from leadership. Tillery returned after a subsequent leader left in 2021. The company he rejoined was working through acquisitions and remote operations, with all the complications those changes carry.

His retrospective included an unusually direct admission: “We didn’t handle the move to remote work very well.” Leaders had spent time explaining the business to investors while failing to give employees comparable attention. The people working inside the company also needed to understand what was happening. Confidence in an executive meeting does not automatically travel to everyone else’s desk.

The remedies included greater visibility across teams and more deliberate people updates. Tillery wanted colleagues from acquired businesses to feel part of a shared organization. The earlier culture had a sillier streak: Friday gatherings once included boat races in a giant inflatable pool inside the office. A workplace can tolerate a surprising amount of informality; uncertainty about its own future requires a more careful response.

We didn’t handle the move to remote work very well.

Jason Tillery, reflecting on Buildout’s transition

Another colleague’s recollection brings the scale back down to a desk. John Krause remembered Tillery inviting him over to preview new features, running scripts, opening a browser, and explaining what customers would be able to do. Krause’s examples ranged from annotating maps to spreadsheet calculations and AI-generated marketing content. The invitation was small; it made work underway visible to another person.

AI, with a job description

In January 2024, Tillery argued publicly against a passive approach to emerging technology. He described a familiar cycle: people dismiss an invention, adopt it later, then treat its success as if it had always been obvious. His concern was the cost of waiting while competitors learned how to use new tools.

That argument allows for experimentation without making every purchase sensible. In a separate discussion of technology adoption, he described buying software whose promised benefits failed to appear. His preferred starting point was a problem the buyer already recognized. Coming from someone selling software, skepticism about the sales pitch is a useful complication.

He also gave brokerage a distinctly human purpose. A client leasing retail space may be trying to open a coffee shop; a buyer of industrial space may be expanding a family business. Paperwork surrounds those decisions, but the decisions involve persuasion, trust, and plans people care about. His case for automation was that it could remove surrounding chores and leave brokers more attention for those conversations.

In that view, a successful tool changes the working day. It earns its place through the task it takes away or the opportunity it makes easier to pursue. The fashionable label on the technology does little to settle either question. Tillery’s position asks the buyer to look at the work before admiring the machinery.

That is also a demanding standard for a software founder. It makes the product answerable to a customer’s ordinary Tuesday, when the novelty has worn off and the outstanding tasks are still outstanding. A buyer does not have to share the developer’s enthusiasm for a particular technical approach. The buyer needs the next piece of work to become easier. This is one reason the early brokerage chores remain relevant to Tillery’s story: they put the founders on the receiving end of their own proposed improvements.

Another company, a familiar problem

On June 25, 2024, Buildout announced Helen Calvin as CEO. Tillery and fellow co-CEO Kris Krisco moved into advisory roles. The handoff gave his Buildout story a clear change of responsibility after years spent moving between engineering and executive work.

In 2024, Tillery co-founded Synopsis. Its focus is business data: bringing information together so companies can integrate and analyze it. Krisco’s public launch account described the frustration behind the venture, recalling the effort spent trying to turn scattered information into something usable. He named Tillery and Samuel Bove as the engineers he had recruited to build the product they had wanted themselves.

The resemblance to the earlier story is straightforward. An experienced team encounters work that keeps consuming attention, then tries to make a product around the problem. The setting has changed from brokerage marketing to data infrastructure. Familiarity with the frustration remains part of the starting capital.

Tillery’s work now also includes an operating partner role at Nexa Equity and a board seat at Leap, where he advises on AI. Away from software, his public interests include woodworking, drawing, and video games. The Lake Forest resident has found room for activities in which making something, solving something, or simply playing can occupy the foreground.

His career leaves a practical question for anyone buying or building a tool: which part of the day deserves a person’s attention? At the beginning, two developers answered by taking on someone else’s chores. Years later, that small act of professional curiosity remains a good place to start.