Production for the album took place during 2007 to 2008 and was handled by several record producers, including Missy Elliott, Stargate, Carvin & Ivan, Wyclef Jean, Jack Splash and Salaam Remi.

Upon its release, Fearless received generally positive reviews from most music critics who complimented its production and Sullivan's vocals, comparing her to female R&B artists such as Alicia Keys and Lauryn Hill.

[16][17] Two other singles "Lions, Tigers & Bears" (which reached number 74 on the Hot 100) and "Dream Big" were later released and were accompanied by music videos.

Sullivan received many comparisons by critics to other well-known female R&B artists, such as Lauryn Hill, Amy Winehouse, Mary J. Blige, and Alicia Keys.

[27][30][31][25][32] AllMusic writer Andy Kellman gave the album four and a half out of five stars and praised her performance, stating: "There's a lot of range on display here, and there is just as much depth.

"[33] NOW's Benjamin Boles commended Sullivan for her "strong voice" and the album's production, stating "she’s pulling from a pleasingly wide range of influences – dropping bits of doo-wop, roots reggae, Motown and hip-hop into the mix while maintaining a consistent feel.

"[26] Houston Chronicle writer Joey Guerra wrote favorably of her songwriting and called the album "a collection brimming with attitude, edge and soul.

"[31] Sal Cinquemani of Slant Magazine gave it four out of five stars and commended Sullivan for her lyrical honesty and musical range.

[28] The Washington Post's Allison Stewart described Fearless as "a mix of awkward-but-novel devices (reggae beats, Daft Punk samples) and nakedly confessional songwriting" and called it "a snappy, intensely human debut.

"[23] Giving the album three out of five stars, About.com's Mark Edward Nero viewed her vocals as "generic and lack emotion or urgency" on some songs, but ultimately wrote that "there are more hits than misses here.

"[25] Okayplayer's Jeff Harvey called it "a well produced urban pop album" and wrote that Sullivan's voice "carries a subtle tenderness that adds intriguing nuance.