The employees of Cloud 9 make their fair share of awful decisions, which is largely what makes Superstore so cfunny. Their jobs are on the line more often than not, and the main characters have to jump through hoops to find a way out of the terrible workplace disasters they create.
The workers grow and evolve throughout the show, and by the series finale, they've all begun to care more about their future careers. It's surprising how much some of their choices helped them in the long run, but that just goes to show that impulse decisions can pay off.
Garrett McNeill: Letting Dina's Birds Out/Not Quitting
Worst: Garrett enjoys making bad decisions at work because the chaos keeps him entertained. However, letting Dina's birds out was an honest mistake. When Dina brought her birds into work, he was so determined to get a candy bar from the vending machine that he opened the cages. Dina was left emotionally devastated, and Garrett spends the rest of the season trying to cover up his mistake.
Best: It's a miracle that Garrett stayed at Cloud 9 for as long as he did. But Garrett hates working in general, so no matter what his job was, Garrett was going to be miserable. His best decision was recognizing that he needed employment and sticking it out at the store no matter how much he wanted to quit.
Sandra Kaluiokalani: Lying About Dating Jeff/Becoming Dina's Assistant Manager
Worst: When rumors started about Sandra dating the district manager, she began to enjoy being the center of attention. Sandra's lies got away from her, and she even started sending presents to herself and claiming they were from Jeff. When the truth came out, everyone started treating her like she was crazy, and Sandra's work environment became miserable.
Best: Sandra's character arc has always been about learning to speak up for herself. Dina picked on Sandra more than anyone else, causing Sandra to fear her. In the series finale, Sandra declares herself Dina's assistant manager at Zephra's new fulfillment center, and Dina is so impressed she goes along with it.
Mateo Liwanag: Bug Bombing The Break Room/Becoming Amy's Assistant
Worst: When Mateo wants to convince Dina that he has Jeff wrapped around his finger, he dresses up as an exterminator and bug bombs the breakroom to fulfill her request. Mateo had no idea how bug bombs work and the toxic fumes take over the entire store. All the customers and employees are forced to flee and get checked out by health officials.
Best: Amy offered Mateo a job as her personal assistant when his immigration status made it impossible for him to be on the payroll. Working as Amy's assistant was a much better role than being a floor worker, and Mateo turned out to be surprisingly good at it.
Dina Fox: Bullying The Employees/Becoming Manager of Zephra's New Fulfillment Center
Worst: There's a difference between teasing and bullying, and Dina does the latter. She's good at getting the employees to stay on task, but she uses fear as a tactic. When Jonah tells Jeff how Dina is treating her subordinates, she gets her first write-up and takes Jonah outside to fight.
Best: Becoming a co-manager of Cloud 9 with Glenn was a smart decision on Dina's part, but managing Zephra's new fulfillment center all by herself was a huge step forward for her career. Dina can do anything she sets her mind to, and a flash-forward reveals that Dina is thriving in her new position.
Glenn Sturgis: Embezzeling Cloud 9 Funds/Opening Sturgis And Son's
Worst: In Glenn's defense, he got the word "embezzlement" confused with "bedazzling." He was keeping Cloud 9's excess funds hidden away in his office and wasn't unaware that what he was doing was illegal. Thankfully, Mateo and Jonah find a way to put the money towards the store and keep him from potentially going to jail.
Best: Glenn stopped being the manager in Superstore Season 4 due to his stress levels, and it was the right call. He took over Cloud 9 again after Amy left, but it was clear that he was never happy managing the store. Reopening Sturgis and Son's gave Glenn the chance to do something he was proud of.
Cheyenne Lee: Getting Bo A Job/Becoming Floor Supervisor
Worst: Bo isn't a character who has a lot of common sense, but Cheyenne loves him regardless. So much so, that she helped him get a job at Cloud 9, knowing he might not be the best match. When he makes plans to rob the store, Cheyenne realizes that if she doesn't stop him, both of them will end up fired.
Best: Cheyenne's talents were often underutilized, so when she applied to the floor supervisor position she proved to everyone just how good she was at her job. It was Cheynne's first step up the career ladder, and Glenn hired her to work with Mateo at Sturgis and Son's after Cloud 9 closed.
Jonah Simms: Hooking Up With Amy At The Store/Picking Up A Cloud 9 Application
Worst: Having sex on the job is a fireable offense, but it's something that happens quite often at Cloud 9. After fighting their feelings for each other for years, Jonah and Amy finally do the deed in the photo lab. However, they were unaware that there was a camera live-streaming them to every Cloud 9 across the globe. It's a miracle they were only suspended.
Best: Jonah was lost when he dropped out of business school, and he applied to Cloud 9 on a whim when he stopped for a snack on his way home to Chicago. People stumble upon the best things in life when they least expect it, and Jonah never could have known that his future wife was working at a big box store in St. Louis. Because of his job at Cloud 9, Jonah found Amy Sosa, started a family with her, and even ended up running for city council.
Amy Sosa: Putting Marcus's Thumb In Guacamole/Quitting Her Executive Job In California
Worst: Since Amy worked at Cloud 9 for so long, there were bound to be mishaps. The worst of them was allowing Marcus to work in the deli and operate a meat slicer with no prior experience. Marcus cuts off his thumb and Amy puts it in a tub of guacamole to keep it cold, which she later loses. When a customer finds a thumb in their package, Dina's blackmailing is the only thing that stops Amy from being fired.
Best: No one was happy with Amy's decision to go to California to work an executive job, and Amy ended up regretting her choice. Career-wise, it was a good move, especially because Amy didn't have a college degree. But Zephra's morals didn't align with her own, and Amy's heart was still in St. Louis. Moving back home to marry Jonah was the key to her happiness, and she even got an executive job with a different company.