He is one-third of the American country music band Lady A, in which he plays guitar, piano and mandolin, and sings backing vocals.

Haywood's father, Van, is a dental instructor/dentist who invented a tooth-whitening method (originally discovered by Bill Klusmeier) and his mother, Angie, is a teacher.

He also sang in Trinity-on-the-Hill United Methodist Church's youth choir called Love Unlimited where he served as the president during his senior year of high school.

He was in a jazz band with Charles's brother Josh Kelley when he attended Lakeside High School and graduated in 2000.

[5] Haywood formed the country music group as Lady Antebellum in 2006, in Nashville, Tennessee along with Charles Kelley and Hillary Scott.

[6] Besides writing for Lady Antebellum, Haywood co-wrote Luke Bryan's 2009 single "Do I"[7] and the track "Love Song" on Miranda Lambert's album Revolution.

[8] In 2004, he engineered and produced, co-wrote and sang harmony vocals on a CD for Mary Bragg titled Certain Simple Things.

Kelley invited Scott to join him and Haywood to write songs together which led to them creating the new group, in which they named Lady Antebellum.

Fans have since nicknamed the group Lady A. Haywood acted as the band's booking agent as they performed in bars and everywhere they could to get noticed.

[10] The group made their debut in 2007 as guest vocalists on Jim Brickman’s single “Never Alone” before signing to Capitol Records Nashville.

[12] They released their second single "Lookin' for a Good Time" in June 2008 and it peaked at Number 11 on Billboard's Hot Country Songs Chart in December 2008.

They also contributed to the AT&T Team USA Soundtrack with the song "I Was Here", which peaked at Number 24 based on downloads on the Bubbling Under Hot 100 chart.

Their fifth single "American Honey" was released on January 11, 2010 and became their third Number 1 on Billboard Hot Country Songs chart in April 2010.

[14] Their sixth single, "Our Kind of Love" was released in May 2010 and became their fourth Number 1 on Billboard Hot Country Songs chart in September 2010.

Their seventh single "Hello World" was released in October 2010 and peaked at Number 6 on Billboard Hot Country Songs chart in April 2011.