Bloomberg Law
Aug. 10, 2020, 8:51 AM

With Stormy School Year Ahead, Chegg Pegs Pac-12’s Top Lawyer

Brian Baxter
Brian Baxter

Woodie Dixon Jr. is transitioning from the upper echelon of law in college athletics to Chegg Inc.'s newest general counsel, but his aim is the same: to help students achieve their educational aspirations.

“I’ve spent the last decade helping student athletes manage that tough balance between sports and academics,” said Dixon, the current general counsel and senior vice president of business affairs for the Pac-12 Conference.

“I thought I could be a value-add at Chegg by bringing some insight into what colleges, universities, and their students face every day,” he said.

His move to Chegg, an educational technology company, also is a noteworthy development for in-house diversity during a time of heightened national awareness over racial inequality.

Dixon, who grew up not far from where George Floyd died at the hands of police in Minneapolis, is switching general counsel roles at a time when Black law department leaders are making inroads in the highest-level corporate jobs.

Dixon said he’s been heartened in recent weeks by the “momentum being built in non-minority groups” to understand the struggles that minorities, especially Blacks, have faced.

He’s also appreciative of the mentors he’s had during a career that’s taken him to China for college basketball and Australia for Pac-12 football. He wants others to have those experiences.

Dixon credits Stephen Pflaum, a partner at Stinson in Minneapolis whose sons played sports with him in high school, with taking an early interest in his career. Dixon said Pflaum helped him study for the SAT and prepare for college. He ultimately went to Amherst, which Pflaum also attended, before moving on to Harvard Law School and Big Law.

John Wooten, a former NFL player and executive who serves as chairman of the Fritz Pollard Alliance, an advocacy group that helped start the league’s Rooney Rule—a requirement that teams interview minority candidates for head coaching positions—helped get Dixon his first in-house job in the NFL’s front office.

The Rooney Rule served as a template for the Mansfield Rule, an initiative designed to increase diversity and inclusion in the U.S. legal profession.

Dixon was as an associate at Dorsey & Whitney and Sidley Austin before moving into the athletic arena. After briefly working for the NFL, in 2004 Dixon became general counsel of the league’s Kansas City Chiefs, winners of this year’s Super Bowl.

Dixon said his decision to join Chegg, where he’ll start Sept. 8 after a decade at the Pac-12, had been in the works for months and wasn’t spawned by a desire to leave the collegiate athletic conference at a time when its business model has faced increased scrutiny from regulators and politicians.

Athletic Power

During his time with the Chiefs and the Pac-12, the new top lawyer at Chegg grew to appreciate the dedication of top-tier athletes, many of whom are now seeking to harness the power of social justice.

In an Aug. 2 letter published by the Players’ Tribune, a group of Pac-12 college football players outlined their concerns about racial injustice, economic rights, and the Covid-19 pandemic. Universities with lucrative athletic programs are currently grappling with how to start a college football season in September while the country copes with the coronavirus.

The Pac-12, through commissioner Larry Scott, has said it’s open to discussing demands made by players.

Dixon said his in-house legal team at the San Francisco-based conference—which includes associate counsel Margaret Carlyle, R. Scott Petersmeyer, and Jagjoth Bhullar—has pulled 18-hour workdays trying to develop protocols to create a safe environment for athletes.

While the Pac-12, like other collegiate athletic conferences, has fought challenges from former student athletes seeking compensation for the use of their names and likeness, Dixon said the Pac-12 has been among the more progressive conferences in its interactions with the players that contribute to its bottom line.

Dixon has sometimes found himself in the middle of that competition. Last year the Pac-12 stripped him from overseeing officiating after Dixon overruled a potential targeting penalty at the end of a 2018 game between the University of Southern California and Washington State University. “You don’t want to be an official,” said Dixon, laughing off the incident.

A spokesman for the conference said it’s yet to announce its plans for Dixon’s replacement as general counsel.

Chegg GC Role

At Chegg, Dixon takes over from former general counsel Dave Borders Jr., who left the Santa Clara, Calif.-based company earlier this year.

The stock prices of many education technology companies are soaring as they reap the benefits from increased demand due to Covid-19. A Chegg spokesman said about 70% of U.S. college students use Chegg products.

Other education-focused companies like Frontline Education Inc. and Laureate Education Inc. have also named new in-house legal leaders this summer ahead of a new school year.

Dixon said he will take time learning the business at Chegg. The company’s legal group currently includes seven lawyers, three staffers, and a consultant in former general counsel Robert Chesnut, who until recently was in-house at Airbnb Inc. Dixon said he expects to make some hires over the next few months.

Chegg confirmed that recruiting firm Spencer Stuart handled Dixon’s placement at the company.

To contact the reporter on this story: Brian Baxter in New York at

To contact the editors responsible for this story: Chris Opfer at