WineShop at Home Leadership Spotlight: Jen O’Leary

Whether it’s pocket income, a dream vacation or a new profession, we can help them create what they want to do. ~Jen O’Leary

“It’s hard to explain to someone what potential is,” says Jen O’Leary, Managing Director of Wine Shop at Home. “You can do so much with this business… it can absolutely replace your full time income. But it’s hard to see that sometimes.”

After three and a half years in business with Wine Shop at Home, Jen is no stranger to realizing potential. “I was the ‘why not?’ girl,” Jen goes on to say. “I wasn’t looking for another job or extra income, but I came across the company and I was really curious because I’d never seen anything like this before.”

Jen’s spirit of “Why not?” inspired her to become a consultant for Wine Shop in 2011 and by the end of 2012 she made the single largest sale of the year, company-wide. Her can-do attitude eventually landed her in a managing director position, which is now her primary source of income.

Today Jen shares with us some of her best tips for success as a WineShop consultant.

The Wine that Sells Itself

Jen always had an interest in wine, though she’d never worked in the industry and had no formal wine education (unless you count various wine trainings when she worked as a waitress in college). Despite the fact that she was already financially stable through her work as a physical therapist assistant, Jen’s interest was piqued when she read about WineShop at Home on the Internet.

“It was important to me to try the wine. I knew that if the wine was good, then it would sell itself. I tried the wine at a tasting, and I thought it was great.”

Jen started working with Diane Nozik on building her business, and in the fall of 2012, she made the largest company sale of the year.

“It really was just purely follow through,” Jen states. “I got [the potential customer’s] contact information and sent him an email. Didn’t hear anything. Then I invited him to a personalized wine tasting and he wasn’t able to attend. Then I put in another call and sent him another email to check back in. Nothing. Finally he replied back and was still interested.

“I took the time to break it out into spreadsheets to find him the best deals, and he eventually ordered 42 cases of personalized wine.”

Voila! The biggest sale of the year is all due to perseverance and follow-up. And Jen’s best tip for successful follow-up?

“You don’t want to be right on top of someone,” Jen says, “but check in regularly to let them know you care about them, because you do!”

What’s Your ‘Why Not?’

Jen emphasizes how happy she is with her business at this point. She is quick to point out that there were certainly moments of adjustment as her loved ones got used to the idea of her running a business, but in general, she found her family to be quite supportive.

“We’ve had our moments but we’ve connected about how we work best together,” she says.

Jen goes on to state, “It’s been a total surprise to me. I had no expectations coming into this [business]… I didn’t have a ‘why,’ I had no idea how much money I could make, I had nothing set in terms of how many tastings I wanted to do. I just really kind of wanted to check it out.

“When people are thinking about becoming a consultant, I tell them my thought process: Why not try it out? Worst case, I make money and have great wine! Best case, I find something I love, create a flexible job around my family, and who knows what other great things may come! It’s a win-win situation. I joined 3 ½ years ago and now I work with great people, I’ve been able to travel to amazing places and I took my kids on a dream vacation to Disney.” So what’s your ‘why not?’

Jen finishes the interview by saying, “Watching [other consultants] create things for their lives and having success is probably the most rewarding aspect of the business.”

Thanks so much, Jen!