Ray Allen is supposed to be retired. He reminds himself of this every now and then. But the tireless community advocate is cut from a different kente cloth. Every career move is intentional, rooted in his enduring determination to build relationships that benefit the greater community. 

Allen’s career journey is on the move once again.  

The former Wisconsin Department of Workforce Development secretary, who came out of retirement in 2019 to lead the Urban League of Greater Madison’s workforce team, has left the local civil rights organization to head the state’s first Black-owned financial institution.

Allen is now president and CEO of Columbia Savings & Loan, a Milwaukee-based financial institution founded in 1924 to provide mortgage loans to the city’s African American community. George E. Gary, a respected business fixture in Milwaukee, oversaw the direction and operations of Columbia for nearly five decades. The Mississippian, who picked cotton in his youth, is stepping away from his executive banking position. Gary is turning 75 this summer and as a gift to himself, he’s decided to slow down a bit, embrace retirement and enjoy his golden years. 

“I believe Ray can carry this institution to the next level,” Gary said. “It’s going to be a real challenge because it’s very competitive today.” 

Relying on his hefty leadership experience in government coupled with his drive and razor-sharp instincts, Allen is up to the challenge. 

“I want to congratulate Mr. Gary on his career and certainly wish him the best as he goes into retirement,” said Allen, who began his executive banking role on June 1. “The goal now is to maintain and enhance the one minority-controlled financial institution in the state of Wisconsin. I want to assist in its net growth, its continued development, and its services to the community. It’s been here 98 years and we want to put it in the position to do another 98 years. “

From Poverty to Prosperity 

Allen is a Milwaukee native with strong roots in Madison. His dad was a factory worker and janitor. His mother was a homemaker and maid. When his dad was injured while working in the factory, a young Ray Allen stepped to help make ends meet. Janitorial work at a rubber company earned Allen is his first wages and savings. 

“My father was very insistent that we be financially responsible,” Allen recalls. “And, although my parents did their best, growing up poor made me realize that I didn’t want to be poor. I wanted to do things that would enhance, you know, my standard economic status in life.” 

Allen earned a journalism degree from UW-Madison and landed a job with John Deere Co. before launching a career in state government.  

“I spent my career, originally with John Deere, in finance,” Allen said.  “So, one of my first career jobs was in finance, and then later, spent time heading up the agency that regulates all the banks and credit unions in the financial system of Wisconsin.  It reinforced my needs to assist our community to grow their wealth.” 

Homeownership is key to significant wealth gains over time, he said. According to a study conducted by the National Association of Realtors, the typical homeowner accumulated $176,123 in home equity in a span of 10 years on a median-priced single-family home. Over 30 years, the wealth gain increased to $307,979. 

“Our focus at Colombia Savings is on expanding our ability to help people become homeowners,” he said. “For the most part, you’re not going to get wealthy unless you’re in a home that’s stable.” 

Allen’s talents were noticed, and he began working for the state. In 2016, former Gov. Scott Walker moved Allen from the Department of Financial Institutions to the Department of Workforce Development, to oversee Wisconsin’s critical role in providing cutting-edge worker training solutions that enable job seekers to acquire the skills necessary to succeed in a 21st century economy. Allen, who served three terms on the Madison School Board, worked for DFI for nearly two decades. Allen also held a stint as the former owner and publisher of the Madison Times Weekly Newspaper. 

He currently serves on more than 10 corporate and community boards, including 100 Black Men, the Overture Center, UMOJA Magazine’s Board of Directors, United Way of Dane County, American Red Cross, Downtown Madison Inc., and Madison College.  

Leaving An Indelible Thumbprint 

Dr. Ruben L. Anthony Jr., president and CEO of the Urban League, said he wanted Allen by his side, knowing the pivotal role his leadership competencies would bring. Amid an era where remote workers outnumber the norm, and job seekers are demanding more flexible work arrangements and increased development opportunities, Anthony looked to Allen for a fresh approach toward optimizing the workforce development team. 

“When Ray joined us in 2019, it was like bringing on an additional CEO,” said Anthony, hiring Allen to lead the Workforce Development Services Division. “I just knew that having him here would be transformative for staff. I watched how he really took on a kind of fatherly and mentor type of interests with the staff.” 

Under Allen’s leadership, the Urban League reached a milestone of placing 1,500 people into jobs by the end of 2021, Anthony beamed. 

“With his workforce development knowledge and expertise, his community credibility and his name recognition, it made it easier to approach the industry and really helped move the program forward,” Anthony added. “I’m pretty sure that Ray will take Columbia Savings & Loan to new heights. They could not have picked a better person to come in and take that organization into a whole new era.” 

The Urban League is one of Greater Madison’s largest community-based providers of career development training and job placement.  With its workforce team, hundreds of Dane County residents found employment at companies like UW Health, UnityPoint Health – Meriter, SSM Health, Exact Sciences, and Findorff. 

Trista Whitehorse, an employment specialist supervisor at the Urban League, relishes the past few years she spent learning and growing under Allen’s leadership.  

“When Ray first came to the Urban League he really laid back and just watched how we worked,” Whitehorse said. “He didn’t make any sweeping changes. He just wanted to see what we were all about and learn our strengths. He placed people in the jobs where their strengths would shine, instead of feeling like somebody didn’t have a place or thinking that they just couldn’t do a job. He was always a big proponent of putting somebody where their strengths lie so that they could excel.” 

She witnessed his successful push to work with companies offering wages over $15 an hour, so they could sustain their households. And when he held “counsel” in his office or over a plate of scrambled eggs and bacon, those who had his attention enhanced their financial literacy. 

“Ray taught me two things,” Whitehorse said. “The first was that the smartest thing to do is to buy property and land. Buy land where you think you’d want to build in 10 years. And, secondly, he told my partner and I that it’s really, really, really hard to make your first million dollars. But, it’s super easy to make millions after that.” 

Whitehorse and her partner recently purchased a home. The millions will come next, she smiled. 

The Importance of Black-Owned Banks  

Black-owned banks offer an alternative for residents who have been consistently discriminated against by other financial institutions. They have typically provided more money to borrowers living in low- and moderate-income than other banks, according to Investopedia. Black-owned banks also are more willing to tolerate higher levels of risk than alternative institutions.  

Without Black-owned banks, countless vulnerable consumers could be forced to rely on high-interest loans from pawnshops and payday lenders for their financing. 

Top Black-Owned Banks and Credit Unions 
  • 1st Choice Credit Union 
  • Alamerica Bank 
  • Brookland Federal Credit Union 
  • Brooklyn Cooperative Federal Credit Union 
  • Carver Federal Savings Bank 
  • Carver State Bank 
  • Citizens Bank 
  • Citizens Trust Bank 
  • City First Bank 
  • Columbia Savings & Loan  
  • Commonwealth National Bank 
  • Credit Union of Atlanta 
  • Faith Community United Credit Union 
  • Faith Cooperative Federal Credit Union 
  • FAMU Federal Credit Union 
  • Financial Health Federal Credit Union 
  • First Independence Bank 
  • First Legacy Community Credit Union 
  • First Security Bank and Trust Company 
  • GN Bank 
  • Greater Kinston Credit Union 
  • Hill District Federal Credit Union 
  • Hope Credit Union 
  • Howard University Employees Federal Credit Union 
  • Industrial Bank 
  • Liberty Bank 
  • Liberty Savings Federal Credit Union 
  • Lower East Side People’s Federal Credit Union 
  • Mechanics & Farmers Bank 
  • Mount Olive Baptist Church Federal Credit Union 
  • Oak Cliff Christian Federal Credit Union 
  • Omega Psi Phi Fraternity Federal Credit Union 
  • OneUnited Bank 
  • OPTUS Bank 
  • South Side Community Federal Credit Union 
  • Southern Teachers & Parents Federal Credit Union 
  • St. Louis Community Credit Union 
  • The Harbor Bank of Maryland 
  • Toledo Urban Federal Credit Union 
  • United Bank of Philadelphia 
  • Unity National Bank 
  • Urban Upbound Federal Credit Union 
  • Virginia State University Federal Credit Union