A fan of professional wrestling since her childhood, Kay first became involved in the wrestling Business in July 2008 when she began training with Mathew Priest and Bill Martel at the Blue Collar Wrestling Alliance (BCWA) in her hometown of Detroit, Michigan. Six months later, she debuted against Shavonne Norrell on December 28. Kay and Norrell engaged in a feud that lasted most of 2009, including a Falls Count Anywhere match at Summer Standoff in August 2009. Kay later began competing against male Wrestlers. At the end of 2010, the BCWA National Championship was vacated, and Kay entered the tournament to determine the new champion. She reached the semi-finals, where she lost to eventual Victor Scotty Primo. Until BCWA's closure in mid-2011, Kay regularly attempted to win the championship.
In mid-2010, Kay began wrestling for Main Event Championship Wrestling. She debuted against Jessicka Havok, and the duo entered a feud which spilled over into other promotions, including Cleveland All-Pro Wrestling. The feud concluded in a two out of three falls anything goes street fight, which was won by Havok. Following the feud, Kay and Havok formed a tag team called Team Be Jealous.
Kay debuted for Ring of Honor (ROH) at the Ring of Honor Wrestling television tapings on November 3, 2012 in a loss to MsChif.
On July 7, 2013, Kay started her first tour of Japan with the World Woman Pro-Wrestling Diana promotion, losing to Keiko Aono in a singles match in Kawasaki. On August 4, Kay and Crazy Mary unsuccessfully challenged Aono and Yumiko Hotta for the WWWD World Tag Team Championship.
On September 28, 2014, Kay made her European debut with the British company Bellatrix Female Warriors, owned by Sweet Saraya, in a losing effort to Bellatrix World Champion, Liberty.
Kay joined Shine Wrestling in 2012. She debuted on the inaugural show, forming a tag team with Taylor Made, and the duo defeated Tracy Taylor and Su Yung. April Hunter was later added to the alliance, with the trio calling themselves Made in Sin. At Shine 7, Made in Sin defeated Taylor, Yung, and Tim in a six-woman tag team match. With the addition of Rain and Ivelisse Vélez, the stable became known as Valkyrie. At Shine 8, Valkyrie defeated Amazing Kong, Angelina Love, Christina Von Eerie, and Mia Yim in an eight-woman tag team match. At Shine 10 in May 2013, Kay defeated Nikki Roxx in a qualifying match for the Shine Championship tournament. When Kay interfered in the main event match between ally Rain and Angelina Love, she was suspended by Lexie Fyfe for 90 days and removed from the tournament. Kay returned at Shine 13 on September 27, teaming with Ivelisse to defeat Jessicka Havok and Amazing Kong, after accidentally clotheslining long-time ally Havok. On the following show, Kay attacked Havok, leading to a singles match at Shine 15, which ended in a no contest. After their next match ended in a double count out, Kay and Havok faced off in a Ybor City street fight in April 2014, which ended in a no contest when Havok was struck by a car as part of the storyline. The rivalry between Kay and Havok culminated in Last Woman Standing match at Shine 20, which Kay won. At Shine 30 on October 2, 2015, Kay defeated Saraya Knight in an anything goes match.
On April 21, 2016, it was reported that Kay had signed with Total Nonstop Action Wrestling (TNA). She made her debut for the promotion, on the same day, during the May tapings of Impact Wrestling, working under the ring name Sienna, by attacking Jade. She then engaged in a feud with both Gail Kim and Jade by joining an alliance with Maria and Allie, establishing herself as a villainess. On the April 24 tapings of Impact Wrestling, Sienna defeated Madison Rayne to become number one contender and face Jade for the TNA Knockouts Championship at Slammiversary On the May 17 episode of Impact Wrestling, Sienna defeated Velvet Sky with Sky's job on the line. She then lost to Gail Kim, after the match, Sienna and Maria assaulted Kim. On the May 31 episode of Impact Wrestling, Sienna and Allie were defeated by Kim and Jade in a tag-team match. At Slammiversary, Sienna captured the TNA Knockouts Championship defeating Jade and Gail Kim after Marti Bell returned and attacked Jade. On August 25, 2016 in Turning Point Sienna lost the TNA Knockouts Championship against Allie in a Five–Way Match, also involving Madison Rayne, Marti Bell, and Jade. Aligned with Maria and Laurel Van Ness, she often attacked Gail Kim.
On January 6, 2017, at the event One Night Only: Live!, Sienna unsuccessfully challenged Rosemary for the TNA Knockouts Championship. The following week on Impact Wrestling, The Lady Squad was ended after her former ally Maria was released from Impact Wrestling. On April 21, 2017, she defeated Christina Von Eerie to win the GFW Women's Championship, making her the first woman to have held the Impact Wrestling Knockouts Championship and the GFW Women's Championship. At Slammiversary, GFW Women's Champion defeated Impact Knockouts Champion Rosemary to unify the titles, entering her second reign as the new Unified GFW Knockouts Champion. At the Destination X, Sienna retained her Knockouts championship against Gail Kim due to interference from the returning Taryn Terrell. Following this, at Bound For Glory 2017 Sienna lost the Knockouts championship to Gail Kim, in a match involving Allie as well. On the March 22 episode of Impact Wrestling, Sienna unsuccessfully challenged Allie for her Knockouts Championship.
