Wilkening started his state career in 1995 as a fiscal and policy analyst for the Health and Human Services Unit at the California Department of Finance before he was appointed Undersecretary of the Health and Human Services Agency in 2008.
As Undersecretary, Wilkening oversaw policy development and implementation, along with the operation of the Agency. Some of the areas he focused on in this role included streamlining government, improving operational efficiency, expanding healthcare coverage, integrating health, behavioral health and social services to promote whole-person care, and improving the delivery of services for people with developmental disabilities.
Wilkening has led efforts to improve how government operates, to better utilize data to improve the delivery of services to clients, and to make programs more client-centered by fostering stronger partnerships across government, academics and the non-profit sector. Under his leadership, CHHS became the first California Agency to establish an Open Data Portal—changing how state agencies interact with the public. Wilkening led a new agile procurement process of the Child Welfare System that has become a model for other state departments. He created an Agency Governance Council and Office of Innovation to accelerate the adoption of alternative ways of solving governmental problems and to foster Agency-wide buy-in to these efforts.
While Undersecretary, he has served as Acting Director of the Department of Public Health, the Department of Developmental Services, and the Department of Child Support Services. In 2018, he was an inaugural winner of the Cliff Allenby award for excellence in public service. He is a frequent speaker at national health care, innovation and technology conferences.
Wilkening received his Bachelor of Arts and Master of Arts degrees from the University of California, Davis.