Jennifer Fly

The Dynamic Force Behind One of Boulder’s Hottest Brokerages

Sitting down with the managing broker of milehimodern’s Boulder office made one thing clear: sitting down is not how she spends much of her time.  

While so many in top management positions spent the past two years fighting to keep staff onboard or handing out proverbial pink layoff slips, this local maven built a team of over 40 agents and established a flourishing hub of mentorship, personal business growth, and luxury home transactions in the Front Range. 

As Jennifer Fly’s track record, energy, and even her name imply, she doesn’t see an opportunity and sit on it. She takes it and soars.

From Assistant to Expert Advisor
Jen’s real estate journey began in high school as an assistant to a local agent in her hometown of Evergreen. But it wasn’t part of the long-term plan — she dreamed of going to law school.  Then life threw some curveballs. The sudden loss of her mother during her senior year was followed shortly by Jen becoming a mother herself. 

“I was 19 and my daughter, Mary, was a baby. I was working and going to school and doing a little bit of everything to just pay the bills,” Jen recounted. “I had to pivot. I thought ‘Well, maybe I should try to work in real estate since I already know a little bit about that.’”

Balancing single motherhood, full-time work as an assistant to an agent in Boulder, and school, Jen earned her real estate license and graduated at the top of her class with a degree in finance and business administration at the University of Colorado. In the twenty-some years since, Jen's experience and her highly attuned way of sharing it with the real estate community continue to garner her recognition as a Boulder County real estate stand-out. 

Embracing Luxury Real Estate and Management
Moving on to work with a local developer allowed Jen to learn the intricacies of luxury real estate from the development side of the business, something she said gave her perspective and a leg up when she made the shift back to sales. Later, Jen joined Colorado Landmark Realtors in downtown Boulder as an assistant to the firm’s owner. She rose to Vice President, a role that made her comfortable with the complexities of contracts and supporting other agents, their deals, and their growth. 

“I found that really rewarding,” she said. 

milehimodern: A Platform for Success
An opportunity for change came two years ago when the owners of Denver’s milehimodern (mhm), Carmelo Paglialunga and Carla Thompson, asked Jen to build its Boulder-area presence. Since then, the brokerage has evolved to include two Boulder offices and welcomed a roster of highly-respected and experienced agents to the team.

Jen still maintains her own client base — something she said she feels lucky to do since not all firms allow or encourage it of their managing brokers. “I’m a more effective managing broker because I still sell. I'm in the trenches with my agents. Especially given the past few years, I think that brings something extra to the table.”

What makes mhm so special, according to Jen, is its “better together” mindset and incredible agent support. “Typically, agents have to look outside their brokerages to find the kind of coaching and business development they get at milehimodern. I was so excited to find a company so invested in the growth of its people.”

Agents at mhm receive one-on-one coaching from on-staff business coaches, as well as continuous learning and development through small-group mastermind sessions, panels, and training. A spirit of collaboration between agents and a culture of support for each other makes for a welcoming vibe that Jen said flows positively into client interactions and deals. 

milehimodern’s approach helps an agent focus on who they are in order to find what works best for them. “There are so many different ways to be successful in real estate. We offer resources for the agent to develop a business that feels true to them,” she explained. “When business growth comes from a place of authenticity, that's what makes someone really love what they do.”

On the tactical side, each agent is assigned a robust team to support their transactions. Specialized pros handle things like visual artistry, listing copy, and more.

Forming a solid support team around agents has led to growth for them individually, Jen assured. Working together works, despite that agents are technically in competition with each other in a housing market with low inventory, a limited supply of clients, and a LOT of other agents.

Social Media That Sells AND Serves
Jen's online presence, most notably her blog and Instagram profile, presents the calm, confident energy you get from Jen herself. But beyond stunning aesthetics and catchy hashtags (Jen is known for her #dreamtubtuesday series), she presents stories with insight, heart, and relevant data. Regularly featuring local businesses, Jen reaches an audience of thousands with everything from favorite local photographers to cultural honors and recognitions to (of course) the incredible luxury homes she and her colleagues at mhm are so adept at selling.

Jen's perspective on social media is that it doesn’t have to be strictly business. It’s an opportunity to share some of who you are so as to not get lost in a sea of real estate sameness. It’s also important to support the local business ecosystem in which one’s clients — whether they already do or simply dream to someday — live, work, and play. 

When Real Estate Runs in the Family
Jen's husband, Dierk, is the COO and General Counsel for Denver-based Kentwood Real Estate, which leads to a friendly and engaging rivalry as well as a collective understanding of the business and its demands. She noted that boundaries can help to keep work from overtaking the conversation at the dinner table.

“When my son Jack was little, he coined the term ‘realting.’ He would be like ‘No realting at dinner!’” she recalled, laughing. “This job is a lifestyle. You don't clock out at five o'clock and you're done. It can be a little tricky to navigate.”

While Jen says she can’t pretend she’s figured it all out perfectly, she thinks they’ve done a good job at mhm helping agents find balance and joy in their work — and in doing it better together. 
Jen prioritizes spending time with her family. They love to travel and explore Colorado with their dogs, Bodie and Cali.  “And,” she added, “we still have a pretty strict rule of no realting at dinner.”

Find Jen on Instagram (@jenniferfly_realtor), Facebook, and, and see what milehimodern is up to in Boulder.