5 Questions with FinTech Founders - Ocrolus

March 15, 2023
by: Cohen Circle Team

Welcome to 5 Questions with FinTech Founders, where we sit down with the next generation of FinTech innovators to hear about how they got started, and where they are going. 

In this installment, we spoke with Sam Bobley, cofounder and CEO of Ocrolus, a document-automation platform that powers the digital lending ecosystem, boosting the efficiency of lenders’ financial data analysis and automating credit decisions across FinTech, mortgage lending, and other banking functions and services. 

Sam started building Ocrolus in his parent’s kitchen when he was 22-years-old. Eight years later, the company has more than 1000 employees globally, across four offices. Along the way, Sam authored a patent application and surrounded himself with a world-class team of coworkers, investors, and advisors. Sam is passionate about fintech, entrepreneurship, and NBA statistics. He was named to Forbes 30 Under 30 in Finance, Class of 2020.

1. Where did the idea for creating a document automation company come from?

Believe it or not, the original use case for Ocrolus was Medicaid application processing. When someone applies for long-term care coverage via Medicaid, they’re required to submit 60 months’ worth of financials to the government for an eligibility assessment. We were shocked to learn that machines are unable to read financial documents with a high degree of accuracy.  

The Google Books initiative digitized over 30 million books, menus, and magazines but ran into poor image quality. They snipped the words, put them into Captcha-style tasks, and convinced their users to help them correct illegible data fields. We took that insight and applied it to financial documents with Ocrolus; we used it as a component of our engine. It’s a counterintuitive concept for a software company. Our plan was to hire a bunch of people to do this verification, and because we addressed the human piece head on, it gave us a competitive advantage and catapulted us to be a category leader.  

2. How have you overcome challenges as you lead the company along its growth trajectory? 

We made a pivot to small business lending when we recognized the massive potential for Ocrolus to increase underwriting efficiency. Pivoting from the original Medicaid use case into lending was a risky decision that turned out to be extremely beneficial for the company. We did a great job of partnering with and listening to our early customers in small business lending, in an effort to evolve our product. Over time we were able to develop fraud detection capabilities and industry-specific analytics that enabled a fantastic product-market fit for Ocrolus. 

We continue to overcome new challenges through tight relationships with our customers. We have regular meetings with our Customer Advisory Board to ensure we stay well informed of market trends and needs. Letting customers lead the way is a great formula for success! 

3. How did the COVID pandemic impact your business?

When the pandemic hit, our core customer base of small business lending was paused overnight as businesses shut down. We pivoted to build infrastructure for PPP (Paycheck Protection Program) loans, helping the local pizza store, florist, and nail salon to get access to PPP capital in an efficient way. We had to adjust our roadmap, because that isn’t the recurring revenue that investors get excited about, but it was a way for us to power through a challenging time.

4What shift have you noticed in customer behavior?

Post-COVID, convenience has become paramount. People want service as fast as possible in as convenient a way as possible. Companies must attract and keep consumers’ attention and have their preferences baked in, which is a huge paradigm shift. At Ocrolus, we’ve created user journey using technology to level the playing field. We’ve adapted to stay in line with the massive shift toward user experience being vital, and we want to be an infrastructure platform that powers that evolution for our partners who offer our technology to their customers.  

5. What do you look for in a VC partner?

Sharing our passion for business development, a great network, and a team with operational experience. We have been fortunate to work with financial partners along our journey who have been impactful in our growth. A number of our investors provided operational help and unlocked customer opportunities for Ocrolus through introductions, prior to even writing a check. Those are the types of partners you want for the long journey ahead.

To learn more about Ocrolus visit

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