Despite only totalling 16 wins in 62 games with the Thunderbirds in his second season, Pickard posted a save percentage of 0.914 and was named to the 2010 WHL West First All-Star Team.

Pickard was sent back to the Lake Erie Monsters on October 25 but was recalled on November 18 after Semyon Varlamov suffered a groin injury.

He would return to the club in late December when Reto Berra injured his ankle, Pickard recorded his first NHL shutout on January 16, 2016 against the New Jersey Devils.

[11][12] A restricted free agent, Pickard signed his first one-way deal with the Avalanche, agreeing to a two-year, $2 million contract on July 5, 2016.

[14] Pickard was poised to be the Golden Knights' backup behind Marc-André Fleury heading into their inaugural season, even going as far to hold a contest with Vegas fans in the design of his goaltender mask.

[17] With the Golden Knights deciding to go with a tandem of Fleury and Subban instead, Pickard was placed on waivers on October 5, in order to be sent to the team's AHL affiliate, the Chicago Wolves.

The following day, he surrendered four goals on six shots against the Toronto Maple Leafs, and was pulled from the net in favour of Anthony Stolarz about twelve minutes into the contest.

A free agent from Arizona, Pickard signed a two-year, $1.5 million contract with the Detroit Red Wings on July 1, 2019, his fifth team in two years.

[23] After a strong pre-season showing, Pickard was assigned to Detroit's affiliate, the Grand Rapids Griffins, with whom he played the majority of the campaign.

[24] On December 1, 2020, prior to the 2020–21 NHL season, Detroit loaned Pickard to the Vienna Capitals of the ICE Hockey League for conditioning purposes following the eight-month break.

[28] While it had initially been intended that his time in the NHL be temporary, he performed sufficiently capably as a backup goaltender to Stuart Skinner that he was retained for the remainder of the season.

However, issues with Skinner's performance in net became increasingly prominent through the first three games of the team's second round series against the Vancouver Canucks, with a save percentage "among the worst in NHL history."

He faced only three shots in the third period, stopping all of them, after which coach Kris Knoblauch opted to start Pickard in the critical Game 4, with the Oilers seeking to avoid a 3–1 series deficit against the Canucks.

[33] His older brother, Chet, a first-round draft pick of the Nashville Predators in 2008, was also a professional goaltender and played with German Deutsche Eishockey Liga (DEL) clubs, the Iserlohn Roosters, Adler Mannheim and Grizzlys Wolfsburg.