How strong systems helped a five-agent team close $130M

Cynthia Krebs Lee, Director of Operations at The Carlisle Group
  • 5 full-time agents 
  • Incorporated in 2022
  • $130M volume 2022
  • Most homes sold in Boston in 2022
  • Top 5 real estate teams in Boston
  • Top 10 real estate teams in Massachusetts

What do the catering and real estate industries have in common? Turns out, it’s a lot more than you might think.

In 2021, self-proclaimed logistics queen Cynthia Krebs Lee needed to pivot her career path. Realizing her background in food and beverage (F&B) gave her a work ethic perfect for real estate, she stepped into the role of Director of Operations at The Carlisle Group.

Today, she’s busy implementing systems for one of the top five teams in Boston — doing approximately $130 million in volume, and having a whole lot of fun in the process.

The Challenge

Too much growth, not enough systems

The Carlisle Group is a family-run business led by Amy Carlisle and her wife Casey Carlisle. Amy serves as the face of the company, while Casey runs things behind the scenes.

“They built the business from the ground up — blood, sweat, and tears — and they made smart choices,” Cynthia says.

This hard work has led The Carlisle Group to grow faster than they could keep up with. Before they knew it, Amy and Casey looked up and realized it was time to hire a Director of Operations.

When Cynthia joined in 2021, there were just two agents under Amy’s leadership. Today, the team has five rockstar agents and is growing! By focusing on building a strong systems-based foundation from the beginning, the team has more than doubled in just one year, while increasing sales momentum.

But a team that’s double the size also means double the transactions, leads, and double (or maybe triple) the need for strong systems to support current and future growth.

That’s where Cynthia’s operational expertise as a fast-moving F&B professional has come into play, with a little help from her trusty lead management platform, Follow Up Boss.

"We have now grown since I joined the team by twice as much. That means more transactions, more sales volume, more systems that need to be in place to make sure the growing pains smooth out."

The Solution

A CRM that evolves with your team

With five agents at all different levels of experience — plus assistants and a marketing team — The Carlisle Group needed a system that would unify all key players.

The team had already adopted Follow Up Boss for lead management prior to Cynthia joining. But with a dedicated team member to lean in and own the operations, The Carlisle Group has now kicked its systems into high gear.

One of the biggest growth challenges for Cynthia and the leadership team has been working with established agents, who already have their own preferred operating norms, and getting them acclimated to new lead management processes. 

Cynthia has successfully brought all agents up to speed while discovering new ways to get even more out of the system.

“I think the fascinating thing about Follow Up Boss is that you could probably dedicate somebody to completely embedding themselves into that and still have things to learn about it. It's constantly changing and evolving.”

Lead generation

For now, the team uses Zillow as a primary lead source, focused on the South Boston zip code in addition to their strong referrals and repeat clients. But they also see leads come in via Redfin and their brokerage, Compass. 

As with most areas, prospects tend to ebb and flow with the local market. Cynthia and the team see greater urgency when the market is active, and less at times when folks are “just looking.”

She and her team have developed robust workflows allowing them to heavily nurture both new leads and past clients, while generating referrals and reviews on sites like Zillow and Google.

“We want to make sure we're top of mind for any opportunity that we can, so we work our sphere pretty significantly,” she explains.

Each and every day, The Carlisle Group agents are pounding the pavement, making calls, and staying busy. But this can get tough, especially on days when it’s difficult to gain traction. For Cynthia, it’s moments like these when collaboration is key to jumpstarting team energy and getting the leads flowing again.

“Sometimes if everyone's having a hard week, we'll just all hit the phones for the day,” Cynthia explains. “Doing something side by side is always easier than sitting in your own cube and wondering how you're going to find a ready client.”

Automations and integrations

When a lead comes in, a Follow Up Boss action plan ensures they’re followed up with immediately.

An organic response gets sent directly to the lead, and the lead gets sent directly to the agent’s inbox to respond right away. “It’s as if you were the one who had been responding to them all along,” Cynthia explains.

Training helps the team sort through the discomfort of following up via phone multiple times and ensures agents don’t feel like they’re “nagging.”

In addition to connecting leads to agents’ inboxes, Cynthia and the team use integrations to streamline communications with their audience. For example, the Mailchimp integration handles the weekly newsletter, helping the marketing team keep in touch with everyone in their database.

Cynthia can easily see who unsubscribed or opened messages, and seamlessly share that info with the team. For example, when a nurture lead clicks a link about open houses, this signals valuable information about their interest level and place in the buying journey.

Reporting and training

For teams of any size, staying on top of leads and agent follow-up is essential.

The Carlisle Group is no exception. Cynthia can quickly pull at-a-glance reports from Follow Up Boss to review team performance at the individual agent or group level.

For her, customizable reporting has been especially useful in gaining buy-in from the team. “Agents aren’t lacking for busyness,” she says. “The last thing they have time for is to sit down and look at a system — they’re salespeople, so that’s not fascinating to them.”

With simple, visual reporting, Cynthia can clearly demonstrate — to senior agents in particular — how the new system can benefit their day-to-day workflows. Seeing the “why” first hand also helps drive agent motivation.

For other Directors of Operations, Cynthia’s advice is to work on your systems in a series of steps. 

"There's so many systems to put in place as a Director of Operations. But when we started by getting into Follow Up Boss, even a little bit at a time, was the best strategy we had."

Client loyalty

Showing appreciation for clients is a core value for the team.

“Appreciation is paramount to The Carlisle Group,” Cynthia says. “We celebrate our clients at every opportunity.” The team hosts highly attended parties in the fall and spring, and even offers a program that awards clients for their appreciation. 

“We really do stay very connected, and it has helped us hugely.” 

The marketing team designs invitations for the events, which are distributed through Follow Up Boss to make sure everything stays connected and gets tracked.

But the personalization doesn’t stop at customized mailers. 

The Carlisle Group pays close attention to past clients’ major life events — from kids going back to school, to marriages and growing families. “Our clients really are part of our family,” Cynthia says. “They become a part of an even bigger system that we make sure we care for and stay top of mind with.” 

Follow Up Boss helps Cynthia and the team keep track of these key details and events to ensure they never miss a milestone. With everything logged into one central system, it’s easy for the team to reach out to each client at the right time and keep those core relationships strong.

The Result

Building a top team in Boston (and beyond)

Today, Cynthia and the team at The Carlisle Group have created a culture that is passionate about clients and agents. 

The team spends time together in person, motivating each other, cheering each other on, and sharing inspirational content from one another, their Compass coaches, and team coaches like Tom Ferry.

“Having that closeness has created an accountability that is second to none,” Cynthia says.

A firm focus on exceptional client service has driven volume to the tune of $130M in sales and recognition for most homes sold in all of Boston for 2022. 

With success this sweet, what’s next for Cynthia and the team at The Carlisle Group? 

In the short term, they have a sales goal of reaching 200 transactions. So far, the team has leaned into a targeted focus in South Boston, which has cemented their reputation as specialists in the area.

But they've also done business in the Boston suburbs, and now that they’ve got a solid team system to grow on, they hope to do even more moving forward.

“We're looking to grow that business as we continue to have more strength organizationally underneath us. We'll be able to take on additional agents that can specialize in the South Shore, the North Shore, and Metro West, and represent us there.”

Of course, Cynthia’s priorities — both short- and long-term — are clear: lining up the team’s systems and making sure they’re running smoothly.

From team hiring and training to high-conversion lead management with Follow Up Boss — she’s here to help The Carlisle Group operate like a well-oiled machine at every step of the journey.

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