Onetime GM exec drives for growth in new career

We need to get a bigger piece of the pie,’ James Gallagher says.

By Mark Gordon
| 8:50 a.m. July 1, 2020
| 2 Free Articles Remaining!

Courtesy. James Gallagher's firm, Stuart Software Solutions, created Structured Income Planning System, SIPS.

Entrepreneurs

In the software industry, especially in the competitive world of catering to investment advisers, it helps to have an edge. James Gallagher’s edge is an escalade. And an avalanche.

Gallagher is president and CEO of Fort Myers-based Stuart Software Solutions. The five-employee company’s flagship creation is the Structured Income Planning System, SIPS Software. It’s a cloud-based subscription platform, Gallagher says, that provides financial advisers a concise planning tool to work with clients on "what if" scenarios. The software analyzes asset allocation, expected returns, taxes, inflation expectations and more.

Motor running

James Gallagher has a lifetime of business lessons in his nearly 20 years working for GM. The list includes:

• Never assume: “One of my bosses once told me he never made a presentation at GM without knowing what the outcome was going to be before he started,” Gallagher says. “I use this lesson today. Clearly understand who you are presenting to, what their problems are and how you can solve those problems. Don’t let politics or motivations or perceptions catch you by surprise.”

• Team player: “Be the facilitator. Leaders are not bosses. They ask questions, let everyone throw in ideas, summarize the ideas and then let the team commit to what they think they are going to do. How much will it cost? When will it be done? Are there any obstacles? How will we measure its success? The really cool part is now they own it — it is their project.”

• Best boss: Gallagher says the best leaders at GM were the ones “that allowed a team structure to work, that embraced innovative thinking” and gave people “enough autonomy to act like an entrepreneur.”

Gallagher recently released a major upgrade of the software, including new features and better functionality, and after a decade of slow-and-steady growth is making a big marketing push for the first time. “It’s not like our product is not successful in what we do,” Gallagher says. “But we need to get a bigger piece of the pie. We want to have some leapfrog-like growth.”

Gallagher, while he’s been at SIPS, and his own wealth management business for a decade, also comes to the field with something probably no one else can claim: he spent 18 years as an executive with General Motors. He oversaw die operations and at one point oversaw thousands of engineers, where he had 14 direct reports. His team invented the Chevrolet Avalanche, refined the Cadillac Escalade and he was named GM engineer of the year for the Trailblazer/Envoy Launch.

“I saw lots of areas of the company, and I did some really cool projects,” Gallagher says. That included airbags, which, he quips, was “really entertaining. We crashed trucks into walls.”

Gallagher brings his engineering mind, and experience navigating one of Corporate America’s biggest bureaucracies, to Stuart Software. (The moniker is based on family name, including his grandfather.) He left the auto industry in 2007, in what he called the “bloodbath” of job cuts at the onset of the recession.

Gallagher and his wife, a Florida native, moved to the Fort Myers area, and he switched careers. He tinkered with the software and launched Waterstone Financial, a wealth management business, to utilize the programs. Back then, SIPS consisted of custom spreadsheets that analyzed different retirement scenarios, helping clients easily understand the outcomes of various financial investment choices, so they could feel more confident and secure. Today Waterstone has 300 to 400 clients with $100 million in assets under management.

“You have to have a slice of the market. If you are too many things to too many people and doing too many things for everyone, you just become oatmeal.' James Gallagher, Structured Income Planning System

The software, meanwhile, was Gallagher’s answer to what he calls the four words that are the bane of any independent registered investment adviser: We’ll think about it. SIPS, he says, is based on providing a map to help clients go from that uncertainty to signing with an adviser.

“Before car makers build anything, automotive engineers run simulations to understand how a vehicle will perform under various road conditions,” he says. “It’s the same idea with retirement planning: People need to run through ‘what-if’ scenarios to understand how their plan can withstand the inevitable financial ups and downs of the markets.”

Gallagher, again leaning on his GM days, says SIPS is his big differentiator in a crowded market, a necessity to build something sustainable. “You have to have a slice of the market,” he says. “If you are too many things to too many people and doing too many things for everyone, you just become oatmeal.”

One of Gallagher shortcomings, he admits, has been marketing and going beyond word of mouth of the software’s success to gain SIPS market share. That’s a big goal for 2020, which not surprisingly, has been dented somewhat by the coronavirus pandemic. “I’m an engineer,” he says adding that he's looking forward to working with his new marketing team.