Gilbert was a professor of entrepreneurial management at HBS. While there he was an adviser to the American Press Institute's Newspaper Next project, which studied ways for newspapers to transition to the digital age. Gilbert also worked closely with Clayton M. Christensen while at HBS. After his time at HBS, Gilbert joined the faculty of BYU–Idaho and served as Associate Academic Vice President of Academic Development; his responsibilities included student leadership, the BYU–Idaho Learning Model, online learning, and the Pathway program.
Deseret Digital Media and ''Deseret News''
In 2009, Gilbert became the CEO of the newly formed Deseret Digital Media, a subsidiary corporation of Deseret Management Corporation, which administers the websites of the Deseret News, Church News, Mormon Times, KSL radio and Deseret Book. In May 2010, Gilbert was appointed president of the Deseret News. He did not replace Jim Wall or Joseph A. Cannon, but filled a new role in the organization. In August 2010, with Gilbert at the helm, the Deseret News laid off 43 percent of its workforce. Gilbert unveiled a set of six themes to guide the paper's coverage—previously distinguished by its lack of oversight from its owner, The Church of Jesus Christ of Latter-day Saints, and a strict devotion to impartiality—going forward: 1. The Family, 2. Financial Responsibility, 3. Excellence in Education, 4. Care for the Needy, 5. Values in Media, and 6. Faith in the Community. Using his theory of "disruption" economics, Gilbert has tried to pinpoint the cost of each story and achieve a more cost-effective story output. In February 2011, Gilbert was the keynote speaker at a conference in St. Petersburg, Florida, where Borrell Associates CEO Gordon Borrell named him the "Innovator of the Year." Gilbert has also spoken to regional newspapers and editors about ways to better monetize journalism. Under Gilbert, the Deseret News has reported a boost in all aspects of its circulation, but some of its numbers have been disproved by The Salt Lake Tribune and Salt Lake City Weekly. As part of Gilbert's plan to "lead and innovate," the Deseret News and KSL created Deseret Connect, a network of freelance contributors under the direction of Matt Sanders. Much of Deseret Connect's content has been featured prominently on the Deseret News homepage, though the print paper has largely remained the work of full- and part-time staff. In November 2011, it was revealed that the mayor of Utah's West Valley City, Michael K. Winder, wrote under a pen name as a Deseret Connect contributor about city hall events, and that his stories were featured in the Deseret News. Gilbert said he was "concerned" that somebody would misrepresent himself in such a way.
BYU–Idaho
On April 13, 2015, Gilbert succeeded Kim B. Clark as president of BYU–Idaho, becoming the institution's 16th president. His appointment had been announced on January 27, 2015 by Russell M. Nelson, then chairman of the Executive Committee of the BYU–Idaho Board of Trustees. Gilbert was formally installed during an inauguration ceremony on September 15, 2015.
BYU–PW
On February 7, 2017, Dieter F. Uchtdorf announced the creation of BYU–PW, a new online higher education organization. Gilbert was appointed to head this new organization, which grew out of BYU–Idaho's Pathway program, originally started in 2009. He was replaced as president of BYU–Idaho by Henry J. Eyring, with his new position as president of BYU–PW effective on May 1, 2017.
