Troy Pospisil - CEO of Ontra - A SAAS platform enabling investment firms to negotiate, digitize, and analyze their contracts

Troy Pospisil is the founder and CEO of Ontra.ai, a tech company that provides contract automation and management solutions for investment firms. While working at a private equity fund, Troy recognized a major pain point. High-volume documents like NDAs were slowing down the investment process. Knowing that the entire private investment industry struggled with the same problem, Troy set out to build an elegant solution.??

In many cases, the best companies to start are those considered “unsexy” yet solve a major pain point. Troy and the team have built an industry-leading business doing exactly that.?

But before Troy got into the contract management business, he was cutting his entrepreneurial chops building sexy businesses. Troy sold knock off handbags one summer when he was 16. He set up purse parties at offices and showed off his Chinese import products. He was so successful that he used the proceeds to buy his first car!?

Later in high school, Troy became a reseller of Baby Phat. He would wake up at 4:30am on weekends to set up a booth at the swap meet, and sell clothes for eight hours straight under the summer sun.?

While in college in NYC, Troy connected with an organic dog food brand that was growing quickly on the West Coast. They didn’t have a distributor in NYC and Troy finagled an opportunity from the manufacturer. Between classes, Troy walked from pet store to pet store in Manhattan, wearing out his shoes. He was a door-to-door salesman with a conversion above 94%.?

And there’s more. Troy started a disposable tableware company while studying abroad in China his junior year. He connected with a manufacturer creating homeware products out of recycled sugar cane pulp. Not only was Troy's new adventure going to save the planet, it enabled him to put his entrepreneurial acumen to work. Troy and his friend made great progress scaling the company. However, the duo decided to sell the business post graduation, and Troy took a job at an established management consulting firm to gain experience working at a large company.?

Later, while working in private equity, Troy realized a major pain point while processing a high volume of NDAs. He reasoned that many of these work flows could be automated. He paid his roommate, who had a background in computer science, to build an MVP. Troy sold the product to 4 customers. Once he felt the business was validated, he left his job to work on building the product full time, and for five years, bootstrapped the company and lived off his savings.?

Despite the stress of not taking a salary for the first two years in business, Troy felt a tremendous sense of purpose. As an entrepreneur, the emotional highs and lows were intense, but there was infinite space for creativity. The challenges of scaling the business drove Troy forward.

For the first few years, Troy slept on friend’s couches while on sales trips and worked himself ragged. He did everything from sales and account management to product. He suffered through rejection, but his persistence and hard work paid off. Even during the most difficult times, Troy’s mentality was that he could overcome anything if he worked hard enough and maintained a positive attitude.?

Ultimately, being bootstrapped taught the team discipline and to maintain sensible economics. They had to be cash flow positive in order to stay afloat, which helped tremendously, especially after the company raised institutional capital to supercharge their growth.?

Today, Ontra has more than 340 employees globally with offices in Europe and Asia. It has raised $250 million from investors that include Blackstone and Battery Ventures.??

The company continues its hyper-growth trajectory and is launching new products to better service its customers. Troy and the team have built an amazing business and brand.?

And they are just getting started.?