Fixing a Broken, Transactional World: Keren Moynihan’s Mission is to Get the Right Businesses Funded by Arming Lenders and Investors with the Right Information.

FinTech Sandbox
Apr 2 · 10 min read

While we may not know exactly how FinTech will impact our future, we have an idea as to who will be leading the charge. Our latest blog series, “The New Faces of FinTech”, spotlights some of the emerging leaders in the FinTech world to get their thoughts on what the future of the industry will look like. Their origin stories are different, their paths to entrepreneurship are unique, but their impacts on their respective industries are significant. No one truly knows what the future of FinTech holds, but these industry leaders may have an inkling as to what we can expect.

Next up in our series is Keren Moynihan, CEO and Co-Founder of Boss Insights. Keren is building a platform that is changing the way lenders, investors, and startups handle the financing process and communicate effectively.

With a diverse background as a commercial banker, wealth manager, and former founder of an impact startup, Keren knows a thing or two about the financial world. She saw firsthand the challenges that came with the loan matching process from both lender and borrower perspectives. Alongside her co-founder, Luke Moynihan, who also happens to be her husband and an expert in building scalable technology, Keren set out to facilitate the flow of capital from lenders who have it to business borrowers who need it. Through Boss Insights, Keren is creating a sustainable future that ensures the right businesses are funded and shrinking the time that takes from months to minutes.

This is part 5 in the 2020 edition of our “The New Faces of FinTech” series created in partnership with growth marketing agency Ideometry. Thanks to all of our interviewees for participating, and thanks to you for reading!

Tell us about Boss Insights?

Keren: Boss Insights is a platform that gathers data on businesses and aggregates it. Our platform does this for lenders, including banks, credit unions, and alternative lenders.

In an era where tech giants have increased the expectations on the consumer front and are now entering the space traditionally occupied by financial institutions, lenders and private capital providers are challenged to offer complete and personalized solutions. Boss Insights’ Compound Data Platform provides a real time understanding of the business client to lenders enabling them to offer customer delight while accelerating capital from months to minutes and proactively approaching businesses with the other services they need. Our mission is to enable businesses to be measured on their merit as opposed to their collateral or personal credit.

Boss Insights created a platform that can access the cloud-based software that businesses use on a day-to-day basis, and use it to accelerate loan approvals from months to minutes. This allows lenders to get a much deeper understanding of what the business’s real needs are, and then proactively offer the right services to the business.

At a high level, we’re changing the relationship between the banks, the credit unions, the alternative lenders and the businesses from something that is transactional and commoditized to something that is more service-oriented and relationship-based.

Has Boss Insights shifted more towards serving traditional lending institutions as opposed to private investors?

Keren: We offer services to both groups and lenders have become a focus. Boss Insights’ Compound Data Platform can qualify leads, gather data and turn it into decisionable insights for due diligence and monitor businesses — this is something that could be beneficial to both investors and lenders. We’ve created AI analytics predicting which companies will get another round of funding, will grow their teams, or exit.

The size of the lending market is orders of magnitude larger than the size of the investing market. There were over 30,000 investment deals done in 2019 and 8 million small and medium businesses that are applying for funding. The lending market is a lot larger even though it receives less splashy coverage than investment deals.

Having said that, investors are starting to become quite data-driven. They’ll purchase data sets and get 50,000 to 100,000 companies to qualify. It’s unrealistic to do this with employees and they are looking for algorithms to scalably screen a company. The chance for an investor to meet a company and then invest in them is, on average, 1 in a 1,000. What an algorithm and AI can do is improve those metrics. We released an AI prediction report last year reviewed and verified by a university data science professor demonstrating that we could improve prediction rates.

What milestones has your company achieved thus far?

Keren:Having released the product to market in mid-2018, we are working with banks and private lenders in Canada and the United States. We have between 100–200 borrowers on the platform. We sell in three geographies (United States, Canada, and the UK), and have had 14 speaking engagements in the past year. We’ve been awarded CLA’s Top 25 Executive Leaders in Lending.

When you’re a startup selling to financial institutions, advisors and mentors will ask, “are you sure this is the space you want to enter?” Sales cycles can take 24 months. We’ve found some extraordinary partners who helped us to reach the market in a shorter time frame. It takes a village to raise a child and it takes an ecosystem to raise a company. We exist because our advisors, accelerators and partners have seen value in Boss Insights and we owe a debt of gratitude to them for their ongoing support.

What’s the origin story of the company?

Keren: In a word, serendipity. It’s the story of ‘fin’ meets ‘tech’. In 2008, I was working at a division of the Toronto Stock Exchange. Interesting times. In 2010, I moved into banking, and worked with over 300 different borrowers in three different industries. I got a very good look into what business borrowers had to go through when they were looking for a commercial loan. I dug in to the details many times to make sure they would get what they needed. That meant I had to get the borrowers to open up, work with credit to find workarounds and ensure the details were there to get things pushed through. The piece of my job that inspired me the most was providing advice and I naturally moved to wealth management. That’s when I was approached to be part of my first startup. It was an impact company that provided up to $1 million to buildings to make them energy efficient and split the savings.

Luke couldn’t have been more different. He knew what he wanted from the time he was 14 and that’s when he started coding. By 18 he started his first software business. He sold it in his late twenties when he moved to Toronto, where his first job involved scaling a company that had just been funded with over $30 million by Georgian Partners. He scaled the tech stack to support a company that grew from 3 to 300 people. Amazon recruiters noticed that. In 2013 he moved to Amazon and ran the tech team responsible for making Amazon’s shipments more efficient.

In 2013, Luke said to me, “Keren, there’s an opportunity to do something big. Small and medium businesses, or even the businesses you work with at the bank don’t have the time or expertise to understand themselves the way Amazon does.” I remember looking at him. He was right, just as he had been on several other trends he’d predicted, but the timing couldn’t have been worse. I just had my first child and I knew it wasn’t the last. I asked him what he was thinking pitching a startup idea in the midst of having a newborn. Luke is not a person who is easily deterred. He doesn’t say a lot, but when he speaks, his words are very impactful. In 2016 when I’d had our third child he brought it up for the second time. Very simply and deliberately he said, “You’ve known me since 2010 and seen me predict 3 trends. I’m telling you there is an opportunity here. Would you like to participate? The rest is history. Boss Insights started in 2017.

Today, 72% of SMB loans and 40% of commercial loans are declined. Of the businesses that receive loans, only half of their needs are actually met. The lenders want to give you the money, so this process should be easier for everyone. But unfortunately, the yardstick for loans is financial statements, credit scores and personal guarantees, which means that we are judging the future of businesses by looking at the past. Looking in the rearview mirror or looking to personal credit has nothing to do with the potential of a business. There are many players on the scene automating small portions like accounting software for example. They then state that they have the issue solved and have provided 360° insights on the business. As a second time founder and a lender who dealt with hundreds of businesses, I challenge these claims. Neither I nor any of the commercial businesses I represented were captured by a document that produces financial information. There’s a giant shaped whole in the knowledge. What about the management team, operations, sales, analytics? Understanding a business is the first step in being able to serve them.

At Boss Insights, we’re pushed every day to figure out how to change the yardstick so that we can measure businesses on their own merit. We want to create a sustainable future that funds the right businesses and ensures the economy continues to grow. That’s what the Boss team is really passionate about.

What makes Boss Insight’s platform unique in the lending space?

Keren: The other providers in the space are offering loan services. We’re a data platform which empowers lenders with a deeper understanding of the borrowers. For lenders that are serious about wanting to understand their business borrower, Boss Insights provides a clear picture in a way that respects the borrower’s privacy while empowering the lender to offer customer delight.

There are many ways this information can be used. It can improve the flow of capital from lenders to borrowers. It can offer proactive recommendations to ancillary revenue services including treasury, cash management, FX and deposit. Most importantly, it changes the nature of the Lender and borrower relationship from transactional to relationship-based.

Are any companies hesitant to hand over the keys to their internal data?

Keren: That’s a very good question, one we get frequently. Today, when a business wants to get a loan, they must provide information, and they’re usually doing it by email. When Boss Insights was pre-approved for a line of credit, the next thing we had to do was send an email with a laundry list of information. With email, there is no control, no security and it’s time consuming.

Boss Insights focuses on offering more security and control to the borrower over their information. It’s on a secure system that companies can control down to the email addresses that have access to the information. They also have the convenience of it and the insights from the information. The loan process becomes much more transparent.

The backend process is still complex, but we offer better user experiences. We want the borrower to have more control on who they share their information with. The lender has the right to understand their entire book of business, and the business owner has the right to control their individual dataset. That’s the stance we take, and that’s the platform we’ve built.

So you founded Boss Insights alongside your husband, Luke Moynihan. What’s the best part about running a company with your significant other?

Keren: The best part is trust. When you’re running a FinTech company and you’re trying to break into the market, there are plenty of challenges that stand in your way. When it comes to working with your co-founder, you want to know that you’re rowing in the same direction. That doesn’t mean you always have to agree, and we often don’t agree on things. But we respect each other very much, and have very complementary skill sets. Having that ability to listen to each other, collaborate with one another, and trust each other ensures we get the best possible product out there.

My career has taken many turns, and the throughline has always been entrepreneurship. That’s not to say it’s easy. It’s incredibly challenging and I’m grateful to be working with someone I very much respect. Luke is in tune with emerging trends. He has his finger on the pulse, and just has a very interesting blend of technical skills and industry understanding. And I get to work with him everyday! I get to be working in a space I care about. It’s not hard to be an entrepreneur and it’s not hard to work with a spouse. It’s a privilege. It’s a gift.

How has your relationship with FinTech Sandbox been?

Keren: One of the best things about being a part of the FinTech Sandbox community is participating in Demo Day during FinTech Week in New York City. It gives us the chance to speak with people like you, for example, and showcase what it is we’re doing on a daily basis and get immediate feedback from a room of brilliant people. That’s pretty amazing. Having the opportunity to work with the data providers is also pretty amazing. Additionally, there are other great founders that are part of this cohort and we get to communicate with them just because we’re part of the group. That’s another amazing perk of working with FinTech Sandbox.

We’re thrilled to feature some of the incredible companies that are currently participating in the FinTech Sandbox program. If you’d like to connect and hear from our interviewees in person, be sure to check them out at the upcoming Demo Day on October 15. It’s a tremendous event that represents a diverse, global group of innovators in fintech and gives others the chance to see our portfolio companies live and up close. We also encourage you to reach out to them directly in the meantime.

Ideometry is a Boston-based full-service marketing agency serving a global client base. With a full suite of creative, development, and strategic services, Ideometry helps growth-stage startups and Fortune 500 companies alike get the business results they’re looking for. If you’re doing something interesting, we’d love to hear from you. Get in touch with us at or email


All things product development and data in finance.

FinTech Sandbox

Written by

Boston-based nonprofit accelerating innovation and collaboration in finance.



All things product development and data in finance. Powered by FinTech Sandbox, Boston based non-profit breaking down barriers to entry for FinTech entrepreneurs by providing free access to quality data.

FinTech Sandbox

Written by

Boston-based nonprofit accelerating innovation and collaboration in finance.



All things product development and data in finance. Powered by FinTech Sandbox, Boston based non-profit breaking down barriers to entry for FinTech entrepreneurs by providing free access to quality data.

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