Program Launched to Help Former Prisoners Land Jobs, and to Resolve "Check the Box" Dilemma

Activist, Former Journalist Named as Project Manager
Jul 6, 2016 4:00 PM ET
Sheila Rule, project manager

July 6, 2016 /3BL Media/ -- With a prison population of 2.3 million in the U.S. and nearly 700,000 people being released annually from the nation’s prisons, there is a dire need for programs that help former prisoners reintegrate into society and establish productive lives. Finding employment is a crucial step in the re-entry process, and that’s where comes in. is an online employment matching system that aligns formerly incarcerated individuals —as well as prisoners on track to be released—with employers who are open to hiring people who have a criminal record. The program is available to job seekers and employers free of charge. 

A key asset of the WhenPeopleWork model is that the employers who sign on already know that their job candidates will be people who have been incarcerated. This eliminates from the pre-interview stage the controversial “check the box” question about a job applicant’s criminal conviction history. WhenPeopleWork is based on a fully transparent hiring process in which prospective employers and employees share the same goals and expectations.

The WhenPeopleWork system will be customized to meet the specific requirements of state, municipal, and federal governments so that they can directly help to find jobs for people nearing release from their correctional facilities. The families of prisoners will be able to access the program from their homes. For former prisoners, the program will offer training on how to use this unique matching system.

The program not only assists people with finding jobs upon their release but also is a tool for furthering their careers as they grow in their new jobs and earn trust and respect in the workplace. Job seekers can update their profile with newly acquired skills and responsibilities to be matched with higher-level positions. A completed profile stays active until the job seeker decides otherwise, all the while continuing to attract and initiate matches.

WhenPeopleWork is owned and operated by LLC of Saratoga Springs, N.Y., which administers two other employment matching services—1stGig, which focuses on jobs for recent college graduates (, and VetsBridge, which specializes in employment for returning veterans of the U.S. Armed Forces ( These programs use a sophisticated algorithm to accurately align an individual’s skills, education, personal attributes, and experiences with the needs of hiring companies. WhenPeopleWork has been developed on the 1stGig and VetsBridge platform and utilizes the same technology in servicing the prisoner re-entry population. 

“Around 70 million Americans have some sort of criminal record,” said President Barack Obama in a 2015 speech at the Rutgers University Center for Law and Justice. “It means millions of Americans have difficulty even getting their foot in the door to try to get a job, much less actually hang on to that job. That's bad for not only those individuals—it's bad for our economy; it’s bad for the communities that desperately need more role models who are gainfully employed. So we’ve got to make sure Americans who’ve paid their debt to society can earn their second chance.”

WhenPeopleWork is uniquely qualified to address the current public policy need to assist formerly incarcerated people assimilate back into society by finding meaningful jobs and careers, thereby reducing the prospects of recidivism.

The challenges of prisoner re-entry are daunting. The U.S. Bureau of Justice Statistics reports that at least 95 percent of all state prisoners will be released at some point, 80 percent of them through parole supervision. And in federal prisons, tens of thousands of people incarcerated for drug offenses are in the process of being released under new Justice Department guidelines and compassionate release policies.

Budget constraints, especially at the state level, have caused the curtailment of critical transitional services including education, vocational training, treatment, and re-entry programs. As a result, recidivism rates have remained substantially unabated over the past decade, and in many states have increased.

To help meet these challenges, WhenPeopleWork is available to contract with city, county, state, and federal agencies and with correctional departments. To encourage employers to participate, WhenPeopleWork provides information on the significant tax advantages and societal benefits of hiring formerly incarcerated people. Employers who sign on are considered partners in the endeavor and will be highlighted on the WhenPeopleWork website.

One of the most distinctive features of the WhenPeopleWork system is its ability to create ongoing social-impact measurements and analytics, which are essential for government policy makers. The data will allow public-sector participants to measure and evaluate their investment in prisoner re-entry employment in terms of the program’s success. Skidmore College sociology professor David Karp, who directs the college’s Project on Restorative Justice, will assist in developing these in-depth analytics. The studies will include the impact that employing formerly incarcerated people has on reducing governmental expenditures through lower recidivism rates. The data will also measure any improvements such as an increase in the pool of taxpayers and a reduction in the strain on social services, as well as outcomes such as stronger families, healthier individuals, and stable neighborhoods. Professor Karp, with the help of his students, will also provide research for WhenPeopleWork on best practices for prisoner re-entry.

“For several years my students and I conducted workshops in New York state prisons on the challenges of re-entry, and I saw firsthand the gap between inmates’ need for employment and the preparation and assistance they received to obtain it,” said Karp, who is a member of the WhenPeopleWork advisory board. “Just as Skidmore College is committed to educating students to become good citizens, WhenPeopleWork is an entrepreneurial enterprise committed to helping people who have been incarcerated become responsible, contributing members of society.”

“Everyone deserves a second chance, especially people who—due to the impacts of poverty, racism, trauma, or abuse—find themselves in jail or prison,” said Jonathan E. Gradess, executive director of the New York State Defenders Association, a statewide non-profit organization whose mission is to improve the quality of publicly supported legal representation to low-income people. Added Gradess, who will serve as an advisor to WhenPeopleWork, “This new innovative program is an important tool for formerly incarcerated men and women looking to transform their lives and obtain good jobs. NYSDA is excited about the potential of WhenPeopleWork to positively change the lives of thousands of people, leading them to productive and purposeful careers.”

WhenPeopleWork will pledge up to 10 percent of pre-tax profits to programs and organizations dedicated to assisting incarcerated and formerly incarcerated people and their families, including programs for prisoner education, public defense, restorative justice, and criminal justice reform. Among the recipients of the funding will be the Skidmore College Project on Restorative Justice and the New York State Defenders Association.

For more information, visit The program’s main office is located at 817 Broadway, 4th floor, New York, N.Y. 10003. To contact the program, email or call 646-480-5735.

Project Manager Appointed to Lead The Effort
WhenPeopleWork has named Sheila Rule, a prominent activist on behalf of incarcerated and formerly incarcerated people, as its project manager. She will work at the program’s main office in New York City.

Rule is co-founder of the Think Outside the Cell Foundation, which works to end the stigma of incarceration and the discriminatory barriers that prevent millions of formerly incarcerated people from fully reintegrating into society. Inspired by her experience of corresponding with incarcerated men and women as a volunteer with the prison ministry program of Riverside Church in New York City, Rule launched her foundation in 2010 to help former prisoners and their families overcome what she calls “the long shadow of prison.”

“The stigma of incarceration is a huge barrier to a successful life,” Rule said, “crippling chances for a decent job, adequate housing, and financial stability. With WhenPeopleWork, people who’ve been in prison will be given a viable second chance. They will be able to build productive lives that demonstrate that they are not their past, they are not their bad choices. In the end, society as a whole will benefit. We will all benefit.”

Rule earned a bachelor’s degree in journalism at the University of Missouri and was a journalist at The New York Times for more than 30 years, working as a reporter, foreign correspondent, and senior editor before retiring in order to fully focus on her current work.

Company Origins, Leadership, and Mission
The parent company of WhenPeopleWork, LLC, was founded in 2012 by First Fairfield Associates, LLC, in partnership with human resources expert Dr. Albert Marco of Madison, Wis. The website had been launched three years earlier and was repositioned in the new partnership. First Fairfield Associates (, with offices in Ridgefield, Conn., and Saratoga Springs, N.Y., is a privately held social-enterprise firm engaged in business and real estate consulting and development work nationwide. The company also provides early-stage venture capital to entrepreneurial start-ups that are committed to achieving positive social impact.

“In keeping with our mission as a socially responsible and innovative company, the First-GIG development team has been diligently working on ways to apply our unique, linear matching algorithm to other important segments of society,” said Marco, a member of the board of “In 2013 we expanded the model to serve our returning veterans by helping them match their unique military skills and experiences to the private job market. Since then we have immersed ourselves not only in helping veterans find meaningful careers but also in helping them throughout their transition experience.”

Added Marco, “For the past year we have worked to come up with an equally unique solution to the challenges facing formerly incarcerated people—as well as employers and state, local, and federal agencies—in providing a safe and equitable mechanism for matching formerly incarcerated people with employers who have already made the decision to hire from within that population.”

Said Richard S. Voog, chairman and chief financial officer of First Fairfield Associates and CEO of First-GIG, “First Fairfield is proud to add WhenPeopleWork to its portfolio of social-impact investments. We are a for-profit entity, so we like to do well, but just as important, we want to do good.”