Jeff Alexander

The J|A Team: Jeff Alexander, Christie O'Connor and Michael Askjaer

In 2018, Jeff Alexander asked himself a pivotal question: How do I get out of the rat race?

Having moved to Hingham from California for his husband’s job in 2004, Jeff felt stuck in a rut. They loved the South Shore, the people, and the seasons—Jeff had fond memories of his college years in New England, too—but the couple’s high-power corporate jobs took a toll. 

For starters, Jeff’s husband traveled to work in Manhattan, leaving Monday mornings and returning Thursday evenings. Jeff, on the other hand, had worked his way up through some of the nation’s top retail brands. Starting in stores at Nordstrom, then to the corporate headquarters at Gap Inc. – first in finance and then moving into merchandising.  Jeff spent more than 20 years in leadership roles at Banana Republic, Pottery Barn and Wolverine Worldwide. 

Upon moving to the South Shore, Jeff founded and ran a pet supply brand called Mascot, which earned him guest appearances on Martha Stewart and brand collaborations with Vineyard Vines and Tommy Hilfiger. He then went back to corporate retail, working as Senior Vice President of Merchandising for Wolverine Worldwide (parent company for Sperry, Merrill, and more). 

“Our son was getting older and we needed a change of pace,” Jeff said. “I thought to myself, if I’m not in corporate retail, what would I do?”

In the background, through all of this, Jeff had always maintained a love for real estate and home design.

“So in 2018, I got my Realtors license and jumped in with both feet.”

Jeff's corporate experience in finance, negotiation, and customer service, teed him up for success.

“It’s always been crystal clear to me that customer service is the key to success,” he said. “Understanding customer needs, listening to the client, and keeping them at the center has been the focus of my career—from retail to real estate.”

Jeff credits his background in understanding clients to his ability to take a 30,000-foot view of a problem, but also being able to dive right into the details at a moment’s notice. His ability to understand, relate to, and communicate with clients has been a throughline in his career; advanced largely by instinct, but his Psychology major and English minor haven’t hurt. 

He’s also always found himself at home working with disruptive, innovative brands.

“That’s why I’ve enjoyed Compass,” he said. “We’re embracing technology with an eye on the client, but we’re supporting the agent and giving them the tools to succeed.”

At Compass, Jeff heads a team with Christie O’Connor and Michael Askjaer. While they all maintain a sharp focus on the client, each of the three real estate powerhouses brings different skills to the table. 

“My background is in merchandising and marketing. Christie and Michael come from finance.  In addition to our sharp customer focus, we each have deep connections in the community.”

“We’re all sincerely looking for what is best for our clients, Jeff said.  “We are genuine, and we treat people the way we expect to be treated.”

They’ve represented $600,000 first-time home buyers, as well as sophisticated sellers with $8 million properties. With each transaction, the team delivers the same experience rooted in their dedication to quality and professionalism. 

Together, the team is producing between 25 and 40 transactions each year, totaling upwards of more than $50 million in annual sales.

The team’s expertise hasn’t gone unnoticed. Every year, Jeff earns himself a spot in Boston Magazine’s Top Producers.  He has also been recognized by the Wall Street Journal as being among the top 1.5% of realtors in the country. 

Despite his sweeping success, Jeff remains grounded in his family, his relationships, and his exercise and yoga practice. 

And when he thinks about his greatest real estate achievement, it’s not the recognition, or the tens of millions in sales.

“For me though, the best award is referrals,” Jeff said. “We get a lot of referral business.  When clients come back, or their friends come to us, that’s the best feeling—it tells me that we’ve grown the business in the best way possible.”




PULLQUOTE: “It’s always been crystal clear to me that customer service is the key to success,” he said. “Understanding customer needs, listening to the client, and keeping them at the center has been the focus of my career—from retail to real estate.”