The Way You Pay Is Who You Are—And If It’s Automated, Your Clients Will Never Leave You

In 1996, when a veteran magazine editor announced he was launching an “all online” magazine, he and his ideas were met with rampant skepticism, if not jeers. This year, that magazine, Slate, celebrates its 25th anniversary. Today, of course, every magazine still publishing has a website. And one of this writer’s alma maters, Glamour, recently ceased its print edition and is now fully online. Like Slate.

The point, of course, is that while businesses should not go “off a cliff” with every new technological innovation, not using tech period will make them seem behind the times. And that is even truer now when one considers how fast technology is moving and how quickly businesses are adopting/changing during the post-pandemic era. Simply put, not adapting and adopting is bad for business. How bad?

Jay H. Goldfarb, Principal at Fortis Management Group LLC, a multi-family office in Boston serving ultra high net worth families nationwide, put it this way: “Invest in technology! If you don’t, it’s unlikely you’ll be around for long.”

In his refreshingly blunt comment, the “technology” Goldfarb was referencing was automated bill pay and invoice resolution. Another fan of this technology is Bob Jacobson, Partner at Friedman & Huey Associates LLP, a boutique certified public accounting firm serving high net worth clients across the nation. 

Jacobson points out another benefit to single family offices (SFOs), multi-family offices (MFOs) and wealth management firms (WMFs) when they provide their HNW clients automated bill pay: “The ROI on bill pay isn’t a dollars and cents question. The ROI is in the overall client relationship, and that’s a huge ROI to me. Bill-paying service to us is like super glue with our clients because when you do it right, they will never leave you.”

Not only does automated bill pay produce “stickiness,” it’s good for your business and the image it projects. So, as the title of this article declares, it does say “who you are,” not just to your current generation of HNW clients, but also to a whole new generation just over the horizon. Consider this: 

  • An estimated $70 trillion of wealth (that’s with a “t”) will be transferred from older to younger Americans over the next two decades. That’s an average of $3.5 trillion per year.
  • The younger generations have high expectations around conducting business digitally. Meaning, as the next generation of HNW individuals gets more engaged in the management of their family’s wealth, SFOs, MFOs and WMFs will increasingly interact with a new generation that will expect a high level of technological sophistication from advisors. How high? Think of this: Today’s college seniors have never known a world without the internet.

Jacobson at Friedman & Huey says his firm is already cultivating a relationship with college seniors among its HNW clients by offering “wealth education for the next generation.”

In terms of who works for your SFO, MFO or WMF, or would want to, research has shown that one in two financial advisors today would consider leaving their firm if they are not provided with the right technological tools for success. Now, the good news. Keep pace with technology, and you get your fair share of that $70 trillion because not only will you appeal to the kids inheriting that money, but you also will attract the best and brightest young people to work for you. Speaking of which, let’s say you have your first meeting with a new generation client and say, “we have a way to streamline your bill paying and invoicing by totally automating it.” Bingo. 

Automated bill pay and invoice resolution also offers some hard, measurable business benefits, including:

Increasing Efficiency and Saving Time 

Automated bill pay, like that offered by, automates busywork so not only SFOs, MFOs and WMFs themselves, but more importantly, their clients can focus on business. For example, see if the description of life before automated bill pay from Josh Levine, Founder and CEO of Cornerstone Family Office, sounds familiar: 

“Our courier would go out once or twice a week to collect invoices from our clients, the team would process them, hand me checks, and I would spend a good chunk of every Friday morning reviewing and signing them and giving them back to the admin team to process and mail. This workflow was clunky and cumbersome and required specific attention to scheduling.”

Levine reports that since implementing automated bill pay, “I no longer have to sign checks; I just have to approve them, which easily saves 30-40 percent of my time.” And he adds, “It also eliminated the need to process and print checks, which has saved our team about 50-60 percent of their time.”

Gaining More Control

With automated bill pay, clients set up approval work flows and custom roles to suit their teams. They also add multiple payment options, from ACH to check to credit card to virtual card to international wire transfers and all on one platform.

Increasing Transaction Security

With automated bill pay, data in transit is encrypted using industry-standard Transport Layer Security (TLS). As Jacobson at Friedman & Huey says, “I’ve heard horror stories from bankers about being defrauded because of email scams or texts that have tricked them into making payments they shouldn’t make. Because automated bill pay from incorporates multiple layers of electronic approval, I have the utmost confidence that if something makes it all the way to the point where I can hit the pay button, there is no easy way to bypass the system.”

Also from a security perspective, another huge win for HNW clients is the difference between sending out a check with a client’s information on it versus protecting that information with an automated bill pay system. 

Making Access Easy for Clients 24/7

Since automated bill pay stores data and invoices for SFOs, MFOs and WMFs and their clients, it provides fast and easy access whenever it is needed. It certainly makes things convenient for clients who, for example, can open the mobile app and approve everything wherever they are using their smartphones.

Avoiding Duplicate Invoices and Payments 

Sometimes an invoice can inadvertently get sent more than once. When that happens, an automated bill pay system flags the invoice indicating it has already been entered. This, of course, ensures there are no double payments, unlike the traditional manual system, which does not have these technological safety nets.  

Increasing Contact Frequency With Clients Strengthens Relationships

With automatic bill pay, SFOs, MFOs and WMFs that currently might engage with clients a half dozen times a year can now have effectively weekly contact with them when processing their bills. So, rather than infrequent sit-down meetings, engaging with clients frequently becomes part of the process and part of the service provided—which, in turn, strengthens relationships with clients.

Being Audit-Ready Basically All the Time

Because payment-related activity is logged and stored electronically, it is available for easy reference basically all the time. It also greatly simplifies and speeds up the usual laborious audit process…for the auditors. 


Imagine this for your business: An easily adaptable technology that can save your clients 30 to 40 percent of their time, that prompts more frequent client contact, taking relationships to a higher level, that burnishes your brand and in turn brings in more business, that prepares you to successfully work with the next HNW generation and that produces that “stickiness” all businesses seek—so much so, that one business owner declares, “they will never leave you.” No need to imagine. It’s already here with automated bill pay. 

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