Jim Woolsey Is the 2019 CLO of the Year

By Elizabeth Loutfi

Throughout his career, Jim Woolsey has focused on progress. As president of DAU, he’s continuing this tradition.
Jim Woolsey started planning for the future of Defense Acquisition University when he became the organization’s president in January 2014, and he hasn’t stopped planning since.

In fact, before leaving his office the day before hopping on a plane to attend Chief Learning Officer’s 2019 Fall Symposium in Chicago, where he would receive this year’s 2019 CLO of the Year award, he sent a note to his team about setting up the next step in evolution they will head at DAU.

As president of DAU, Woolsey oversees all acquisition education activities and programs, including online and instructor-led training, knowledge sharing, job support tools, consulting engagement, customized workshops, research and the university’s strategic partnerships across five geographical regions, which support and serve a defense acquisition workforce of more than 173,000 military and federal civilian employees.

Over the course of nearly six years, Woolsey has been at the helm of several sweeping changes and has helped launch various new initiatives that have transformed the institution’s learning and development.

The Right Man for the Job

Even before joining DAU, Woolsey already knew the defense acquisition business inside and out, thanks to positions he held previously. But his path was not entirely unusual for a CLO.

“When I read about other CLOs, coming from business is not entirely out of the realm, but my background is very analytical,” he said. “I have worked in defense acquisition, so I do understand the business. And I’ve changed jobs quite a few times, and being able to change is a handy habit right now for people and organizations because we all have to be quick on our feet.”

Woolsey started his career as a structures engineer for the Navy, his first introduction to defense acquisition. At the time, the thought of working in L&D wasn’t even on his radar. He joined because he was fascinated by airplanes, which he had the opportunity to build — a very satisfying experience, he said.

He eventually moved over to the analysis and research side, serving as assistant director of the Institute for Defense Analyses, a think tank, where he oversaw cost analysis and research and served on a defense science board task force. Woolsey then worked for the undersecretary of defense for acquisition, technology and logistics and served as the first deputy director for performance assessment for the office of Performance Assessment and Root Cause Analyses at the U.S. Department of Defense.

A Quickening of Pace

Fast forward to 2014. In his first year as president of DAU, Woolsey oversaw the expansion of its College of Contract Management, in partnership with the Defense Contract Management Agency. Under Woolsey, DAU grew its curriculum from seven courses to 42, resulting in $3.8 million saved in vendor and student/instructor travel costs, 43,000 hours of student/instructor time saved and further support to the Army from the DCMA. Woolsey also helped launch the Services Acquisition Workshop Program that same year, a success for DAU’s overall business performance. These efforts earned him a 2016 Learning In Practice Trailblazer Award and Innovation Award.

That same year, Woolsey was awarded the Business Partnership award for developing a learning program for executive training in partnership with the Missile Defense Agency.

Jim Woolsey
A Quickening of Pace

Fast forward to 2014. In his first year as president of DAU, Woolsey oversaw the expansion of its College of Contract Management, in partnership with the Defense Contract Management Agency. Under Woolsey, DAU grew its curriculum from seven courses to 42, resulting in $3.8 million saved in vendor and student/instructor travel costs, 43,000 hours of student/instructor time saved and further support to the Army from the DCMA. Woolsey also helped launch the Services Acquisition Workshop Program that same year, a success for DAU’s overall business performance. These efforts earned him a 2016 Learning In Practice Trailblazer Award and Innovation Award.

That same year, Woolsey was awarded the Business Partnership award for developing a learning program for executive training in partnership with the Missile Defense Agency.

Jim Woolsey

Woolsey also led DAU in a redesign of leadership courses for the Defense Systems Management College, adopted the use of a new learning management system universitywide and personally envisioned, designed and implemented a new learning model, the Acquisition Learning Model, for the defense acquisition workforce.

“We’re in a dynamic world as everyone knows; it’s a dynamic world for learning as it is for defense.”
— Jim Woolsey, president, DAU

Right now, defense acquisition is in a crucial time of evolution — a response to a competitive and complex global security environment, as noted by then-Defense Secretary James Mattis in the 2018 National Defense Strategy.

For defense acquisition, Undersecretary of Defense for Acquisition and Sustainment Ellen Lord knew this new national defense mindset meant an emphasis on speed and taking more risks, as well as working with a lot of different kinds of people they’ve never worked with before, Woolsey said.

“She’s the steward of the acquisition system and has to make it work in the way that the nation and the warfighter need it to work,” he said.

Through DAU, he added, Woolsey acts as Lord’s partner and ambassador for her knowledge and her message to the people who make up the defense acquisition workforce.

“We’re in a dynamic world as everyone knows; it’s a dynamic world for learning as it is for defense,” Woolsey said.

This year, in addition to being named CLO of the Year, Woolsey also received a silver medal in the Trailblazer category of Chief Learning Officer’s Learning In Practice Awards for his involvement overseeing the Acquisition Leadership Development Initiative, which was based off stakeholder input.

“Where [this initiative] really fits in the bigger picture is that at DAU, we’ve made a strategic choice to focus on our customers rather than focusing on technology or efficiency,” Woolsey said. “We’re focused on the people who are doing the learning.”

Always Moving Forward

Woolsey said he’s gotten to do all the things he’s wanted to do, and he considers himself lucky to have his current job. He enjoys the successes they have as a team, and when that 20 minutes is up, he said, he’s excited for the next challenge. Right now he’s focused on innovative progress.

“We are constantly changing and striving to improve because the workforce that we serve and ultimately the warfighter that we serve have to have that,” he said.

Elizabeth Loutfi is Chief Learning Officer’s associate editor.