“This is nobody’s job – and nobody should be wasting even a second of their time on it,” says Yashwanth Madhusudhan, CEO and co-founder of Fyle, of the work and hassle involved in managing expenses. Fyle, the start-up launched seven years ago, is all about making that a reality, he explains.

“The work involved in administering staff expenses isn’t core to anyone’s role, but it’s just so time-consuming and frustrating,” he says. “We want to get to a point where people just say ‘Fyle it’ when they’re dealing with this issue.”

Fyle’s focus is on corporate credit cards, which have become the default way for many US companies to ensure their staff can pay for business expenses. Indeed, credit cards were the second-most-sought-after form of financing for small businesses in the US last year according to Federal Reserve.

Around $1.4 trillion is spent on these cards each year; employers then have to check that credit card bills have been run up appropriately – and ensure that the data from them flows through into the company’s finance and accounting systems.

The problems with the status quo are three-fold according to Fyle. First, financial controllers at companies that have issued credit cards to staff have little visibility over how they are being used. To see what’s been spent on them, they have to wait for statements to arrive at the end of each month, or log into their credit card provider’s portal and download transaction data, typically in a format that is far from user-friendly.

The second issue, Fyle maintains, is that even when the business has all the data it needs, this information has to be entered into its accounts manually. Finance departments are wasting valuable time processing what may be thousands of transactions in this way. Problem number three is the challenge of dealing with receipts, with many companies stuck in a cycle of chasing staff to supply the correct receipts for their spending.

Fyle’s solution is a software package that taps straight into the business’s credit card transaction data; managers can then monitor spending as it happens through Fyle’s app. The data also comes in a form that can be automatically be integrated into the accounting software used by the business, so that it doesn’t have to be re-entered. And when an employee uses their credit card, Fyne’s software sends them a message asking them to submit a photo of the receipt.

The obvious place to go for this data and functionality is the credit card provider itself. In practice, however, most US banks providing credit cards are unable or unwilling to help. They’ve either not built the technology infrastructure necessary to provide transaction data in this way, or they’re not prepared to put such technology to work other than for their largest corporate customers.

The result is that credit card providers – with the exception of new fintech entrants to the market – have not typically offered this functionality to small business customers. Nor have providers been prepared to offer it to Fyne.

The company’s solution has been to focus on another link in the credit card payments chain. Last year, Fyne announced a partnership with Visa that allows it to access the transaction data of corporate credit card holders – assuming they agree. And this week it is announcing a similar deal with Mastercard. The result is that it will be able to offer its services to the vast majority of US businesses that have issued credit cards to staff.

“This integration will empower small businesses to harness the power of real-time visibility for any card that suits their business needs,” says Madhusudhan of the Mastercard collaboration. “We are democratising access to businesses’ own expense data and removing their dependence on the issuing bank.”

It’s a software-as-a-service solution through which small businesses pay a monthly fee per user of Fyne’s technology. Irrespective of which bank they use for corporate credit cards, Fyne is then able to supply them with real-time data, secured from Visa and Mastercard, on how employees are using their cards. This information can be used for monitoring purposes, and can also be dropped straight into accounting software. Employees get reminders of their employers’ expenses policies, and messages to submit their receipts with a picture sent by their phone.

It’s an elegant way to deal with US banks’ reluctance to address this problem for themselves. But one irony of Fyne’s approach is that it is increasingly attracting interest from these very same banks. Small business banking in the US is becoming more competitive, particularly as new fintechs enter the market, prompting providers to look for points of competitive advantage. Fyne therefore offers a white label service to banks, enabling them to offer small business customers the same functionality, built into their banking apps.

In time, therefore, Fyne’s distribution model may change. Right now, it makes most of its revenues from selling its subscription straight to small businesses. In future, it may earn more from providing its services within the bank’s own value proposition, charging the bank, rather than its small business customers, for the software.

Either way, small businesses can’t afford to waste more time on administering expenses, argues Madhusudhan. “We need to automate as much of this work as possible,” he says. “We can do that directly with small businesses, or through their banks, but the goal will be the same, providing real-time visibility and automation.”

Have you watched the television show “Succession?” And who hasn’t? Logan Roy is trying to figure out who should head up his company – Waystar Royco. Are you struggling with the same question with your family business? What if it is time to think about passing your company on to the next generation, but, there is no one ready to pass it to?

Don’t panic! The situation arises more frequently these days for several reasons. It could be you have no children to pass the company to, there could be a lack of trust in the offspring to lead the company, a lack of interest in the heirs or a conflict between family members when it is time to pass the reins.

There are other options which include transitioning the business to outside leadership – perhaps while a family heir is being groomed – or to its employees through an employee stock ownership plan, or ESOP; selling the business; or simply closing it.

Often, the reflexive response is to sell. Given today’s pace of disruptive change, no one will fault you since the market for private companies continues strong. Plus, financial advisors and attorneys assisting owners in such succession matters are typically incented to advise selling the business (if they generate revenue only when a transaction occurs, as is often the case).

In my experience family owners move too quickly to a sale. Instead, they should consider all the alternatives and benefits that can derive from keeping the business operating as a family concern. This is an area I have spent much time talking to company owners about all their ownership alternatives.

First, take an honest and dispassionate reality check and determine if the business truly possesses the requisite capital, products, infrastructure, leadership, committed employees and innovation to continue to thrive. If it does not, a sale may maximize value. But if the business possesses these critical strengths, then the family can create more wealth by continuing to operate it.

According to a study conducted by KMPG and the Step Project the family business leaders in their study stated that choosing the right successor will, indeed, be their most important legacy and a moment of personal pride.

In determining what to do, an owner should ask these questions: How important is the business to the family and its legacy? Are you sensitive to the disruption a sale will have on employees? On your community? Have you considered an ESOP? Who within the family could be groomed to take charge? And can an outsider as CEO keep a strong family business thriving?

If your answers incline you towards keeping the company, two approaches exist for bringing forward the next CEO for a family business when one is not immediately present:

No. 1: Coach a family member Remember, the second generation needn’t be a carbon copy of the successful founder, because those skills aren’t necessarily what’s needed in the next generation(s). What’s generally required is engagement, pride and commitment.

Indeed, mapping skills needed for the business against those of possible future family leaders or employees should be ongoing. There is a wealth of training and coaching opportunities that exist for family businesses. Coaching can bring forward the skills necessary.

No. 2: Hire an outside CEO. Yes, this takes time. Typically, it requires six months to find the person and another six months to know if the executive is a good fit. If it is, the outsider can be hired for the long-term or act as the regent until the likely family heir develops the necessary leadership skills. Compensation should be structured to reward performance and, if the executive will be handing over the reins, to encourage turning the business over in good shape.

Be mindful that it may take more than once to bring the right outsider onboard. That was the experience of one of my clients, a nationally known family-owned company, whose second outside president, who had worked with the company at one time, was the right person to lead the company. Now president and chief operating officer, he became CEO in 2020 when the chairperson and CEO, the daughter of the founder, retired. Since he joined as No. 2, the business has continued to thrive.

The message here: Don’t despair and rush to sell your business if an heir isn’t apparent. With the investment of some energy and time, alternatives that can keep the business in the family and retain its distinct culture and values are at hand. I’d love to sit down with Logan Roy and talk about his options.