From Cold Calling To Running a $2B Business: Former Overstock President Shares Her Selling Secrets


The year was 2001. Amazon sold only books, Netflix was but a dream, and even the smallest piece of furniture was not sold digitally. When Stormy Simon joined the team at Overstock, it was a different, much less hyper-connected world, but this future-focused executive saw where the retail game was going. Simon, who went from a role in B2B sales in 2001 to the company's President in 2016, was a pioneer in a still unchartered space.

When asked what lead her to digital sales, Simon's answer is simple; “I placed an order online and the light bulb went off. I was so excited to get the package, and it just hit me that traditional retail, the way we are all programmed to shop, was about to change. I knew this was going to stick, this was going to work."

Simon, who imagined and executed Overstock's well-known “The Secret Of The Big O" campaign, had an unconventional route to success; one that involved such potential career-deterrents as teenage pregnancy and forgoing a college education. Although she joined Overstock as an entry-level temp, thanks to a steady stream of promotions Simon went on to generate almost $2B for the company. What got her there was a blend of tenacity and foresight, as well as a penchant for scrappy innovation.

“I have a really nontraditional path," says Simon, who was on welfare for a short amount of time before landing the job at Overstock. “I was a mom by the time I was 18, had my second at 21, and was divorced soon thereafter. My biggest fear was not providing for my boys (Austin, age 31; and Dylan, age 27). I knew I had to succeed, because as a teenage mom, people would tell me I was going to ruin my life. Those naysayers fueled me to think I have to do it."

After attending Salt Lake Community College for a year, Simon decided to take on a job in the home video distribution industry, with the hopes of learning through a hands-on approach, rather than sitting in a classroom.

“I chose to stay with the job instead of going back to school," says Simon, who was quickly promoted to Manager of Sales Accounts and Advertising within the company. “In the early 90s, home video was becoming very big, and I viewed the job as a stepping stone to that education I decided to forgo."

With a plan to relocate to Las Vegas for an event management startup, suddenly on September 11, 2001, the wheels fell off Simon's plan.

“I was out there for 90 days then suddenly everyone stopped coming to Vegas," says Simon. “I decided to do some soul searching. My boys were 15 and 12 and I thought I would maybe go back to school. I thought I had to serve the world, not be in business."

After a brief stint wrapping presents, which Simon picked because it felt uncomplicated and happiness-imparting, Simon took on a temp job at Overstock, making outbound calls for bulk sales, not knowing that the gig would later blossom into a full-fledged passion project.

“We were buying things like vacuums, sunglasses, dishes, luggage, sheets and rugs and selling them as they came in," says Simon, adding that at the time Overstock was truly offering "overstock," AKA warehouse bulk inventory. “I was detached from the job; just killing time before figuring out my life's work, but what happened was that I came in and killed it. On a team of four males and myself everyone was trying to sell a million dollars of luggage, and I did it."

Simon says that when the CEO at the time asked if any employee would be interested in buying stocks in the company, Simon put $800 in, leaving her bank account nearly empty. The move caught the attention of her supervisor, further propelling her forward at Overstock.

Possibly one of Simon's biggest achievements while at Overstock was her conception of “The Secret Of The Big O" campaign in 2003, which would go on to take the company from $250M to $500M in 18 months. Simon says she approached the CEO with the idea to advertise the company on television, something she noticed other dot coms at the time were avoiding.

“I had a feeling [television advertising] might be cheap since no one else in our space was doing it and that it would really make us stand out," she says. After winning the approval of the board, Simon wrote the commercial, hired the talent, and flew to LA to oversee the entire process.

“That campaign killed it," says Simon, who to this day, remembers the script verbatim. “It went; 'Have you discovered the secret of the big O? Overstock.com, an online outlet where everything is always on sale. Buy best-selling books 25 percent below Amazon with $2.95 shipping and live customer service 24/7. It's all waiting for you."

After the commercial hit the airways, Simon says revenue went into triple digit growth, helping fuel her next appointment to Vice President of Branding, where she oversaw the video, books, and music departments.

“I grew the business to $20M in 3 years," says Simon. "Because I had been in video distribution business, I started calling studios I knew like Paramount, Columbia, and Sony, bringing in those relationship and ultimately I grew the business to $100M"

The next focus for Simon was bringing customer service in-house, and focusing it on care, rather than simply servicing clients.

“I wanted to lower customer service costs while bringing it in house," says Simon, who within eight months brought on 450 customer care (a term Simon coined) agents, and dropped costs by a full percent. “Changing from 'service' to 'care' was a big cultural change. Now it was about servicing, not upselling. The industry followed. We lead a shift; suddenly everybody wanted to care."

Simon said as she navigated her career, she was always confident, but that along the way there were challenges, and even overt offenses launched her way, simply because she was a woman. “Being a woman has always been something of an issue, especially when I was younger," says Simon. “Compliments are one thing, but there are underlying tones that can hide behind it and make you feel creepy. And in my 20s, as someone cute with no college degree, I always felt like I had to prove my smarts."

Simon goes on to say, “ I had no idea I'd be smacked on the butt by my boss, and then have guilt thinking maybe I tolerated it. I would think 'I'm learning so much, advancing and is it really worth it? As a single mom I couldn't disrupt my income, so I'd bit the bullet and just accept that slap on the ass."

Ultimately Simon believes her experiences were all learning lessons, and she is thankful for the fact that they made her stronger. “It took me a long time to really get it, to really understand that yes [gender equality in the workplace] is an issue," she says. “As you get older you can put out an energy where that kind of behavior will just not be accepted. You create the hands-off armor. There are a lot of men out there who admire strong women (and search for those) and let them fly which is a beautiful thing."

The Amazon Effect

In today's online shopping-obsessed world, SWAAY asked Simon her thoughts on how brands can innovate their digital sales model now. Amazon, was unsurprisingly, the topic of the day. “Amazon is a good race to watch," she says, adding; “I think there's a lot to be done actually."

With rumors that Amazon is going to get into the furniture business, Simon believes a revolution may be afoot for Overstock and other similarly-positioned digital retailers.

“If Amazon goes into furniture, I feel it could really change everything," she says. "They have the infrastructure, and their purchase of Whole foods gives them that a unique insight into neighborhoods that tend to be more affluent. If they get that data and if they can bring online furniture to local markets that would be brilliant. It would mean ordering a couch online and getting it the next day. It would mean teaming up with local furniture stores using geolocation services then pushing the sales through Amazon. It would be revolutionary."

Looking to her own future, Simon, who now lives in small farming community in Utah, says she is expanding her horizons. To that end, she is currently on the board of a cannabis company that is dedicated to highlighting its medical properties, and working on several projects, including a local startup incubator for women. “I needed a time out," says Simon, who left the company in July of last year. “I'm entertaining ideas and opportunities right now, and my eyes are wide open."

3 min read

Help! I’m Dating a Jerk!

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Help! I'm Dating a Jerk!

Dear Armchair Psychologist,
I've been dating my boyfriend for a year. After spending some vacation time with him and realizing he is not treating me the way I like I'm wondering — what do I do? I need him to be kinder and softer to me but he says simply, "chivalry is not his thing." I believe when two people decide to be together they need to adjust to each other. I don't think or feel my boyfriend is adjusting to what's important to me. Should I try to explain to him what's important to me, accept him for what he is, or leave him as I'm just not happy and the little gestures are important to me?
- Loveless Woman

Dear Loveless Woman,

I am saddened you aren't getting your needs met in your relationship. Intimacy and affection are important to sustain a healthy relationship. It's troubling that even though you have expressed your needs to your boyfriend that it's fallen on deaf ears. You need to explore, with a therapist, why you have sought out this type of relationship and why you have stayed in it, even when it's making you chronically unhappy? Your belief that couples should adjust to each other is correct to some degree. These things often include compromising and bending on things like who gets the bigger closet or where to go for dinner. However, it's a tall order to ask someone to change their personality and if your boyfriend is indeed a jerk, like you say, who refuses to acknowledge your love language or express kindness and softness, then maybe you should find a partner who will embrace you while being chivalrous.

- The Armchair Psychologist

Update to HELP! My Date is Uncircumcised and I'm Grossed Out!

Hi Armchair Psychologist,
Just wanted to let you know that your article was really offensive to read. Do you refer to women's genitals as: "gross," "ghasty," "smelly," or otherwise? Humans are not perfect, each of us is different and you should emphasize this. I hope that man finds a partner that will love and accept him rather than tearing him down. Which gender has a whole aisle devoted to their "special" hygiene needs? I can tell you it's not men.
With love,
Male Reader

Dear Male Reader,

Thank you for your thoughtful feedback to my Armchair Psychologist column. My email response bounced so am writing you here. I am so sorry I offended you. It wasn't my intention. I actually meant to be sardonic and make the writer see how ridiculous she sounded for the harsh language she used to describe her date. I obviously failed at this sneer since you think I meant to be offensive. Many apologies. I'll do better. Have a wonderful day and keep writing us with your thoughts.

- Ubah, The Armchair Psychologist

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