How Dana Wines Found an Automotive Career She Never Knew Existed

Four or five years ago, Dana Wines was a credit union branch manager who wanted something different. She wasn't looking for automotive. She wasn't picturing a dealership at all. She was scrolling job listings when a finance manager posting caught her eye, and it happened to be at a dealership.

If you've ever considered a job outside your field and thought, that's close enough to what I know, you already understand how Dana got her start. She knew auto loans. She knew finance. She figured she would be working the other side of a transaction she already understood.

The dealership had other plans. Instead of finance, they put her in sales.

That single redirection carried Dana Wines through sales, into finance, and eventually into a role that didn't exist before she arrived: Training Director for We Auto's four dealerships across Michigan and Tennessee. Her path is a case study in something Women In Automotive talks about often. You don't always find your place in this industry. Sometimes you build it.

"Just Teach Me What I Need to Know"

Dana walked onto the sales floor as one of only two women, with no automotive sales experience. But she knew what she brought with her. She knew how to talk to people. She was naturally competitive, sharpened by years of playing college basketball. And she wasn't afraid to ask for help.

She found the top performing woman on the floor and made her an offer: teach me the product, and I'll bring the rest. Her approach became simple. "I sold myself first," she says. "I sold the dealership second. And then I sold the vehicle."

Eight months later, she was promoted into finance. She still holds the Ann Arbor record for selling six cars in a single five hour Saturday shift, a fact she still uses to needle the same sales guys, now her friends, who like to remind her the store used to close earlier back then.

This isn't a story about a woman enduring a male dominated floor. Dana loved competing with those guys, and that energy is exactly the point. Her confidence didn't come from ignoring that she was one of two women in the room. It came from deciding her difference wasn't something to apologize for.

From Proving Herself to Becoming Part of the Team

Being one of the only women on the floor came with real discomfort, and Dana doesn't pretend otherwise. She was establishing herself in an environment built by and for men, and she felt that pressure every day. But she didn't try to become someone else to manage it. She performed, and she let the results speak.

Six months in, a few of the salesmen admitted they had expected her to be stiff and reserved when she walked in for her interview. Once they saw how she worked, they became some of her biggest supporters, a dynamic that repeated itself when she moved into finance as the only woman on that team.

Finance asked something different of her. Sales had rewarded her for thinking about her own numbers, her own KPIs, her own gross. Finance required a shift from I to we. Dana had to learn to think about the team's deals, the team's responsibilities, the team's performance, not only her own. Every promotion in her career has asked her to become a different kind of teammate before it asked her to become a better performer.

The Strength She Didn't Have to Learn

Somewhere along the way, Dana became the person her coworkers sent the hardest customers to. The ones with a chip on their shoulder. The ones who walked in already frustrated. She had a gift for disarming them, making them laugh, and turning a tense interaction into an easy one.

She remembered birthdays. She asked about people's kids. She asked how someone's day was going before she asked them to sign anything. "You have to care about people," she says, "before you can get them to buy into you as a person too."

That instinct never stayed confined to the customer side of her desk. She carried it into every relationship with coworkers, and it became the foundation for everything she would eventually build as a trainer. Long before anyone gave her a title, Dana had already figured out that the thing that made her good at her job was never really product knowledge. It was paying attention to people.

"We've Created This Position With You in Mind"

About a year into her finance role, Dana was called into a room with her dealer principal and the corporate controller. We Auto didn't have a training department. They wanted to build one, and they wanted to build it around her.

"We've created this position with you in mind," they told her, "and we want you to take your creativity and run with it."

Sit with that for a moment. Someone at We Auto looked at Dana and recognized that her value to the organization went beyond what she could sell or structure. It was something the company didn't have a box for yet, so they built the box around her.

Dana has spent the two and a half years since then building the training function across all four of We Auto's dealerships, two in the Ann Arbor, Michigan area and two in the Nashville, Tennessee area, with more locations likely on the way.

Building the Onboarding She Wished She'd Had

On Dana's first day in sales, she sat at a desk for six hours before a manager came over to tell her what to do. Nobody had forgotten about her. Everyone was simply busy. She was proactive enough to get up, introduce herself, and start asking questions on her own.

She never forgot how that felt, and when she became Training Director, she made a decision. That was never happening to anyone else again.

She rebuilt onboarding around a simple principle: new employees are spoken to, remembered, and intentionally brought into the organization from day one. She still goes back to the people she used to work beside on the sales floor and in finance and asks them directly. Where are we lacking? What do you need? What should we be teaching? What are we already doing well?

Some of her former coworkers now teach inside We Auto University as subject matter experts. The best training programs, it turns out, aren't necessarily built by the person who knows everything. They're built by someone who remembers exactly what it felt like not to know anything.

Turning Training Into a Game

Ask Dana what effective training looks like beyond processes, products, and compliance, and she'll tell you it has to be fun. People in dealerships are competitive by nature, she says, so instead of fighting that instinct, she built training around it.

She created the We Auto League, which runs from March through December. Sales managers become coaches. Finance managers become assistant coaches. Employees get drafted onto teams complete with logos, gear, and a draft day with ESPN music playing in the background. Dealerships compete by division, East against West, with a North and South division on the way as We Auto grows.

The competitions aren't just for show. Employees practice the actual skills they need with real customers: presenting pencils, walkaround videos, trade appraisal videos. Every week, teams go head to head, and the season builds toward a Super Bowl in December, with the winning team's name added to a trophy and a company trip on the line.

The results show up in more than morale. Dana has watched salespeople move from eight or nine cars a month to ten or fifteen. That kind of growth shows up in a paycheck, and it shows up at home, which is exactly what We Auto's mission statement points toward: we inspire people to grow, making our families, team, and community proud.

But What If You Train Them and They Leave

It's one of the most common arguments against investing in people, and Dana was asked directly what she says to it. Her answer reveals more about We Auto's culture than any mission statement could.

If someone leaves, that's okay, Dana says. Automotive isn't for everybody, and We Auto is upfront about that from the very first day. Her job as Training Director is to do everything she can to help a person grow while they're there. If that growth eventually carries them somewhere else, she shakes their hand and wishes them well.

Developing people isn't only valuable when the company gets to keep the result. That kind of culture, one that invests in people regardless of how long they stay, may be exactly what makes people want to stay in the first place.

Women Don't Have to Just Sell Cars

Dana wants women considering an automotive career to understand how much territory it actually covers. Sales. Finance. Service advising. Technicians. Accounting. Training. Careers that don't even have a name yet, until someone builds one around the right person, the way We Auto built hers.

She's living proof, and she doesn't just talk about it. She recruits. A server who provides great service gets her business card. So does a bartender. So does a flight attendant. She once handed her card to a Delta employee on her way home from a Women In Automotive conference because the woman's service was that good, and Dana thought she'd be excellent in automotive.

Her question is simple. "How much better could the automotive business be with more of us doing our jobs?"

The Leadership That Made Her Story Possible

When asked what she wished had been asked, Dana didn't talk about herself. She talked about her dealer principal, the leader who never treated her differently because she was a woman, who recognized her work early, told her he wanted her on the team long term, and gave her equitable compensation and opportunity from the start.

Dana knows not every woman in this industry has had that experience. She's met women at WIA whose stories look very different, and her message to them is simple: there are good people and good dealerships out there. Her success came from her own hard work, but it also came from someone who opened the door and meant it. Both things had to be true. Women need to bet on themselves, and organizations need to be willing to bet on them too.

Bet on Yourself

Think about the reader scrolling job listings the way Dana once did, looking at something she has never pictured herself doing.

Dana hadn't pictured it either. She didn't know the product. She didn't know where automotive would take her. She says plainly that she was nervous, and that she was scared.

"If you're ever going to bet on somebody," she says, "bet on yourself. You're going to win a hundred percent of the time, and you will be astonished what comes after that."

You don't have to know exactly where you fit before you walk through the door. Sometimes you find the role. Sometimes the role finds you. And sometimes, if you're willing to bet on yourself and someone else is willing to recognize what you bring, you get to build a role that wasn't there before.

That's the invitation Women In Automotive extends to every woman weighing a future in this industry, whether you're just starting to look or you're ready to build something that doesn't exist yet. Join the Women In Automotive community to connect with women like Dana Wines who are doing exactly that.