Working at Gap Was the Best Job Ever—Until the Company Fell Apart

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So how could Gap—a brand once ubiquitous in popular culture—crash so hard? In my on-and-off seven-year career with the company, I witnessed the fallout of many of its failures. I was just a salesperson, with no insight into the actual numbers, but I was aware of the hundreds of thousands of dollars in sales pressure my managers were up against. These numbers would translate to individual sale associate goals—expectations that were hammered into us daily and went from reasonable to unreal overnight.

Still, when I started with Gap, the luxury shopping center where my store was located was a dream world for part-time employment. From a radiant and airy sales floor full of customers to the equally glowing team of fellow Gappers ready to assist them, it was a pleasure cruise through a pre-recession world seemingly unaffected by the decline of the American mall.

It started with the employee training. Along with learning how to "board fold" a shirt and "perfect fold" a pair of Long & Leans, I remember watching a video mash-up of Gap's influence on popular culture. References ranged from the then-iconic musician-driven commercials and print ads to the mid-90s Saturday Night Live skits about the "Gap girls." Gap seemed to understand its once-cool place in American culture. Was the company hoping this waning cool-yet-inclusive, "everybody in" vibe would translate to the work experience? If so, it worked.

I began working for Gap shortly after it had reopened Cherry Creek's huge maze of a store—which included a Gap, Gap Kids, Baby Gap, Gap Maternity and Gap Body—as part of a massive remodeling project of several stores across the country. Looking back on it now, I can't believe a global corporation's answer to slowing sales was to close down several top-performing stores for months just to remodel them. But once reopened, the new and improved Gaps were gorgeous. My store pulled in several million in sales alone each year. We were a high-traffic, high-demand Gap located in a high-end shopping center, and we were busy all the time—not just during the typical holiday and back-to-school shopping seasons.

The store was split into "rooms" like a house, with hardwood floors and sleek lighting, making for the most pleasurable of casual shopping experiences. The centerpiece of the store wasn't a display of Gap's newest apparel but a rather literal living room for customers to hang out in. Tired dads lazed about on comfy couches reading fresh copies of newspapers provided by the store, while Gap commercials played on TV screens set inside the charming wooden wardrobes where we hid extra hangers and plastic shopping bags.

Shoppers were offered bottles of water as they tried on new styles in dressing rooms with their names written on the doors in chalk. Salespeople whirled around them with racks of apparel. A curated soundtrack featuring the likes of Joy Division, Rilo Kiley, and Amy Winehouse was pumped through the store for shoppers as they perused all-white special edition pieces by Doo.Ri, Rodarte and Thakoon, work designed exclusively for Gap.

Along with Gap's remodel came an upgrade in the employee break rooms. As a sales associate, your backstage downtime is generally spent staring at a white wall next to a mini-fridge or inside a storeroom full of brown boxes while hurriedly shoving Panda Express in your mouth. But here, we had a couch in a sunroom, complete with a full-size refrigerator, a kitchenette, an employee computer with free internet, and a television with cable. Plus, a multi-million dollar store could afford to have a ton of people working multiple shifts throughout the day, so lunchtime was often a potluck gathering of friends or a group TV-watching party. It was kind of unheard of for a job at the mall.

Then the Great Recession of 2008 hit. Everything changed and the party was over. The sales floor was empty of customers, and our big white shelves gathered dust where a bulging sweater inventory used to sit.

Once the customers left, the sales positions began disappearing, too. Most people who lost their jobs were seasonal, but the rest of us started being scheduled less than eight hours a week. Even for a part-timer like me, this was financially excruciating. To make things worse, the company employed a horrible new scheduling system that cut our shifts into tiny pieces, working 3.75 hours here and 7.5 hours there. This program also forced all employees into the same mold—we all had to be available at least 40 hours a week, even though we were being given barely any work. Like many decisions Gap Inc. made at this time, from my salesperson's perspective, it made no sense.

Then there was the issue of the barren, walled-off wasteland that the sales floor had become. The pre-recession remodel that had turned a normal retail space into a series of themed rooms now created the perfect tangle of hidden corners for shoplifters. The handful of staff working each shift could only provide so much security for thousands of square feet of retail. The wardrobes with TVs were gone, the newspapers unsubscribed to, the couches removed. The area of the store where we stocked shiny rows of free bottled water became a storage area for socks. As sales associates, we were constantly battling the myth that we could be in more than one place at one time. There weren't even enough of us working to assist the customers we did have.

There were also the embarrassing bargain basement-style sales. Each day that I came into work, I had to memorize which sections of the store were "buy one thing get another thing half off." The next day it would be "spend $200 get 25 percent off." By the weekend it would be "50 percent off of some jeans (but not all jeans)." It was total chaos.

Customers with Gap credit cards would open their mailboxes to find coupons that were equally manic and confusing, then bring them in for us to decipher together like it was some sort of sale puzzle quest. Shoppers were constantly mentioning Gap's desperation, a topic that I had a hard time deflecting as a salesperson.

The worst part came when we were required  to push shoppers to apply for the Gap credit card. I don't know what was more humiliating: begging customers to get their credit checked during a recession, or going to "Gap card boot camp"—a Saturday training class involving role-playing scenarios overseen by a militant assistant manager—when I didn't make my Gap credit card sign-up goals.

Even when customers actually were clamoring for a style, like colored denim or skinny jeans, Gap failed to capitalize on the demand. In a recent Fast Company profile, new Gap CEO Art Peck lamented that the company's great "Colored Denim Period" was over. But from my point of view, Gap never treated these new kinds of denim as the staples that they'd clearly become. We couldn't keep colored denim or skinny jeans on the shelves, yet we'd have to wait weeks for replenishment. By the that time the jeans had arrived, our customers had were most likely headed to Forever 21 or H&M for their denim basics (as many of us Gap employees were also doing.)

In the many, many retail jobs I've held over my lifetime, I've witnessed plenty of instances where the people at the very top are giving orders without ever having set foot on the battlefield of the retail sales floor. But Gap Inc.'s maneuvers during this time were so out of touch with what was really happening in its stores that it almost seemed like self-sabotage. With a leadership focused on signing up customers for Gap cards and cutting down a knowledgeable, passionate staff, it felt like the company was working against the people who knew it best.

Peck is known for being technologically savvy, and his plan to save Gap leans heavily on digital upgrades and interactive in-store components. I don't know if it'll work, but I do know that the Gap shopper of yesterday appreciated the human element of the customer-service experience. Whatever the changes bring, I hope they can capture the inherent coolness Gap once embodied so many decades ago. I left Gap in 2013, and even though it was a shell of the place I once loved, I still miss it. My old store is probably going to survive this round of closures. But the simple, enjoyable part-time retail job I used to hold there—it sounds like that might be lost forever.