Easterbrook began his professional career as an accountant for Mauldin & Jenkins CPA's from 1989 to 1991. He then worked as an Accounting Manager at Evonik Degussa from 1990 to 2000, followed by a position as Assistant Controller at the same company from 2002 to 2006. In 2009, he became Director of Finance and Controlling in North and South America for Outokumpu Stainless Steel, where he was part of the management team that turned a near-bankrupt site into a profitable one, saving over 1,000 jobs at the Calvert mill. From 2005 to 2009, he also worked as a contractor for Easterbrook Homes, specializing in rebuilding homes after Hurricane Katrina.

Easterbrook's political career began when he ran for the Alabama House of Representatives District 65 in 2018, defeating incumbent Democrat Elaine Beech with 52.8% of the vote. He was reelected in 2022, defeating Democratic opponent Marcus Caster with 72.7% of the vote after winning the Republican primary against Dee Ann Campbell with 70.3% of the vote.

In the Alabama House of Representatives, Easterbrook has served on multiple committees including the Education Policy Committee, Insurance Committee, State Government Committee, and Transportation, Utilities and Infrastructure Committee. He currently serves as Vice Chair of the Insurance Committee and is a member of the Agriculture and Forestry Committee, Baldwin County Legislation Committee, and Ways and Means General Fund Committee. Easterbrook has sponsored several pieces of legislation that have been signed into law, including bills related to food enrichment requirements for corn masa products, game breeder licenses, agricultural assessments on cotton sales, and shark alert systems.

Easterbrook is married to his high school sweetheart, Betsy, and they have been married for over 30 years. The couple has two children- Turner, who is a recent college graduate and newlywed, and Jeremiah, who passed away at 12 years of age. The family makes their home in Four Points, Alabama, where they enjoy fellowship at a small, rural church. Easterbrook is most at home working on his farm and managing timber in Deer Park, following in the footsteps of his maternal grandfather who taught him to appreciate and work the land.