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Three employee retention secrets from former Levi’s exec-turned-entrepreneur Anna Brockway

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How I Hire Series Former Levi Jeans Exec

Three employee retention secrets from former Levi’s exec-turned-entrepreneur Anna Brockway

Businesses must work harder than ever to engage and retain their best people — and once they’re gone, it’s difficult to replace them. 80% of HR leaders can’t get top talent through the door and 70% of teams can’t keep high-performers according to Sage research .

Anna Brockaway

But that’s not to say every company struggles with retention. Consider Anna Brockway, a former Levi’s marketing executive who co-founded Chairish, an online marketplace for vintage furniture. A self-described “compulsive redecorator,” Brockway turned her love of interior design into a business. She grew it from a startup that began in her San Francisco dining room five years ago into a thriving company with more than 70 employees.

Brockway has turned the reasons those employees might seek a new job — growth opportunities, among others — into an advantage. The trick? She encourages employees to explore different parts of the business, or, as she puts it, an “all-you-can-eat salad bar” of opportunities.

So far, it’s worked. Chairish, boasts a high employee retention rate, Brockway says.

Finding self-starters and problem-solvers

Brockway is partial to candidates who have excelled in challenging work environments. “I like to work with people who have shown results without a lot of resources,” she explains. “I look for people who come from life or personal experiences where they’ve just had to figure stuff out.”

Succeeding within—and in spite of—a difficult corporate environment shows character, Brockway says. “If they can succeed in a place like that and are liked and respected, that means a lot to me,” she says.

For Brockway, it’s all about making the best of a situation, no matter what the circumstances or resources, and finding a way to help the company grow within your role.

“You have to show initiative, show smarts and show hustle,” she says. “You have to have the ability to not just stand around waiting for perfect to happen. Recognize that there is no perfect—you have to build it.”

Three employee retention secrets from former Levi’s exec-turned-entrepreneur Anna Brockway

Looking beyond the résumé

In the early days, Chairish’s small team had broad responsibilities, but roles have become more specialized as the company has grown.

Brockway now hires for all sorts of roles—product and engineering teams to handle site design and function, an inventory team responsible for finding the best vintage furniture suppliers in the country, marketers who drive site traffic and increase brand awareness, and a logistics team that figures out how to ship big, bulky items from buyers to sellers.

The best person for a role isn’t always the person whose résumé perfectly matches the job description. That’s why she places a lot of emphasis on the background of candidates outside of their work history.

“I look for people who aren’t afraid of doing things they haven’t done before—people with somewhat odd career paths that may not be a perfect match with their background that they’ve been successful. That shows a willingness to learn and to take risks.”

An iconic American brand, a valuable lesson learned

Before founding Chairish, Brockway worked at Levi Strauss & Co. as the vice president of worldwide marketing. At Levi’s, Brockway focused on hiring candidates who were passionate about the product. “The thing I looked for at Levi’s was fanatics—people who were fanatics about fashion and denim,” she says.

Brockway has carried that mindset to Chairish. She seeks out people who genuinely care about design.

“The people we hire need to have a passion for the business we are in,” she says. “Hiring an analytics person who loves home design can be tricky, but it’s important.”

Brockway has found that people who have a passion for the design industry are the ones who will stay committed and strive to grow the business, even when the going gets tough.

“Like all businesses, we deal with stuff that’s not fun,” she says. “There’s a lot of grind. But if you’re working on something you love, it helps you get through the harder stuff and keeps you inspired.”

Brockway recognizes that specialized knowledge is important in hiring, but it’s not necessarily the most essential criteria in filling a role. “You can’t really hire tech and commerce experts right now because the landscape is changing so quickly,” she explains. “Whatever you’re an expert in now will mostly be irrelevant within the next 14 months.”

This changing landscape makes the ability to adapt and grow a crucial skill for new hires.

“While expertise is nice and certainly useful, the ability to learn is equally, if not more, important,” she says. “The one thing we know for sure is that we don’t know what is coming next.”

Learn more about how to create a people-centric company that will not only attract but keep your best talent, driving business growth.


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