In the broad landscape of corporate social responsibility and diversity, equity, and inclusion (DEI), few stories are as compelling and transformative as that of Ken Oliver. As Vice President of Corporate Social Responsibility for Checkr and the Executive Director of their corporate foundation checkr.org, Oliver brings a unique perspective shaped by profound personal experiences. His journey from spending nearly 24 years in the California prison system, including almost a decade in solitary confinement, to leading social impact and DEI initiatives in the tech industry, underscores a remarkable transition from incarceration to leadership and influential advocacy.
This feature delves into Oliver’s path to Checkr, his contributions to criminal justice reform, and his vision for integrating fair chance hiring practices within corporate America.
Early Life and Incarceration
Ken Oliver’s story is not just a narrative of personal resilience; it’s a testament to the power of transformation and advocacy. Oliver’s early life took an unexpected turn when he found himself serving a lengthy sentence in the California prison system. “I served 24 years in California prison,” Oliver shares—“almost 10 of those years in solitary confinement.” Released in June 2019, his reentry into society was marked by an immediate transition to meaningful work as a paralegal at a public interest law firm, a role that leveraged his self-taught legal expertise developed during his incarceration.
This initial position was just the beginning of Oliver’s advocacy journey. Recognizing his potential extended well beyond writing legal briefs, his employers quickly propelled him into a policy director role, where he became a vocal advocate for criminal justice reform at the state level. Oliver’s work in California’s state capital of Sacramento, advocating for policies around the restoration of voting rights, fines and fees legislation, and sentencing reform, laid the groundwork for his future endeavors in bridging the gap between criminal justice and corporate responsibility.
Transition to Advocacy and Reform
Oliver’s transition from a legal professional to a leading voice in criminal justice reform and corporate social responsibility was fueled by his proximity and a deep understanding of the systemic barriers faced by justice-impacted individuals. His advocacy work, particularly in Sacramento, was not just about changing laws but transforming perceptions. Oliver explains, “During that time, one of my job responsibilities was to teach companies in Silicon Valley about ‘Ban the Box.’ I would always advance the conversation around Ban the Box being just one issue.”
Ban the Box refers to efforts in many states nationwide to prohibit employers from including a box asking about past criminal convictions on job applications. While employers would still have access to such information further along in the hiring process, the elimination at the early stages has been seen as a way to help qualified candidates with arrest or conviction histories get their foot in the door so that employers are better able to consider a candidate in their entirety, rather than distilled down to their past involvement with the legal system.
Oliver recognized that Ban the Box was just part of the problem facing people with arrest or conviction records. These individuals could also benefit from programs designed to help them address skills gaps resulting from years spent behind bars and out of the corporate or educational arenas, for example.
Oliver was surprised to find how receptive the companies he worked with were to these ideas, and together they discussed ways to address skills gaps. Oliver began to design a program aimed at intensive skills-development programs to instill key corporate competencies in a high-intensity environment for six-to-nine months.
This period marked a significant evolution in Oliver’s career, as he began to see the potential for broader impact beyond the legal and policy realms. His efforts to bridge the skills gaps for justice-impacted individuals through education and corporate partnerships underscored a pivotal shift in how DEI initiatives could be implemented in the tech industry and beyond.
Historic Investment in Innovation
Leveraging his knowledge and findings, Oliver set out to design a 12 month residentially based tech training program that would provide justice impacted individuals a campus like environment that would provide housing, financial stipends, personal leadership development, financial literacy, digital literacy, and tech certifications in tracks like project management, IT Support, digital marketing, and UX/UI design. He also designed an immersive change management training program for employers to educate them on how to build out more inclusive hiring practices that included justice impacted talent. To fund the aspirations of this ambitious endeavor Oliver lobbied California lawmakers to reimagine reentry with an investment in people. Legislators and the governor agreed and awarded Oliver $28.5M to build out this first of its kind program.
Making an Impact at Checkr
Oliver’s journey in advocacy and reform ultimately led him to Checkr, a company at the intersection of technology and social impact. Checkr’s commitment to fair chance hiring resonated with Oliver’s own personal mission, making his decision to join the company a natural progression of his career. Oliver recalls that after Checkr took the 1% Pledge they “really wanted to focus on their social impact and evangelizing fair chance hiring as a core principle in corporate America.”
Checkr was interested in bringing in someone whose personal lived experience aligned with the impact they were trying to make. “And so, they hired me as the VP of Corporate Social Responsibility,” Oliver says. “And then they also wanted me to set up a corporate foundation for them, which I did. So currently my role is VP of Corporate Social Responsibility and also the executive director of their corporate foundation.”
In his dual role at Checkr, Oliver has been instrumental in shaping the company’s approach to DEI, leveraging his lived experience and expertise to champion fair chance hiring practices. His work involves not just internal policy development but also external advocacy, educating other corporations on the importance of inclusive hiring practices and the potential of justice-impacted individuals to contribute meaningfully to the workforce.
At Checkr, Ken Oliver has spearheaded initiatives that not only advocate for fair chance hiring but also demonstrate how businesses can actively contribute to societal change. His approach intertwines DEI efforts with corporate social responsibility, creating a model that other companies can emulate. Oliver’s work is grounded in the belief that employment is a critical step in breaking the cycle of recidivism and poverty.
Vision for the Future
Looking ahead, Ken Oliver envisions a future where fair chance hiring is not an exception but a norm within corporate America. His aspirations extend beyond Checkr, with the hope of influencing broader industry practices and policies that support justice-impacted individuals. and the democratization of opportunity for all marginalized or underrepresented groups.
Oliver’s vision is rooted in a deep understanding of the transformative power of employment and the need for systemic change to address the barriers faced by those with arrest records. By continuing to advocate for fair chance hiring and inclusive practices, Oliver hopes to contribute to a more equitable and just society where everyone has the opportunity to succeed.
Ken Oliver’s journey from incarceration to corporate executive and policy advocate is not just inspiring; it’s a call to action and a wake-up call for companies everywhere. Through his advocacy, Oliver has demonstrated the profound impact that inclusive hiring practices can have on individuals, the organizations they serve, and society as a whole. His work at Checkr serves as a testament to the power of second chances and the wealth of talent available for organizations willing to look beyond an applicant’s past.
Lin Grensing-Pophal is a Contributing Editor at HR Daily Advisor.