What does it take to build a high-performing new home sales team in today’s changing market? For Cassie Smith, Director of Sales and Design for Chesapeake Homes, success begins with a combination of strong relationships, consistent sales habits, creative leadership, accountability, and genuine commitment to developing people.
I was thrilled to have my great friend Cassie join me on my EXCIA Podcast to discuss her journey from the restaurant business to leading sales strategy, design, team development, and customer experience across Chesapeake Homes’ four divisions. Ranked among the nation’s top homebuilders and generating more than $300 million in annual sales, Chesapeake Homes has created a culture in which people are encouraged to learn, grow, and succeed together.
Cassie grew up in Virginia Beach and began her career in the restaurant industry. She progressed from hostess to busser, server, line cook, and eventually manager. She also earned a degree in education and originally intended to become a middle school mathematics teacher. Although her career ultimately took a different path, both experiences gave Cassie skills that would prove invaluable in new home sales.
Restaurant professionals learn to remain composed under pressure, ask good questions, solve problems quickly, and create an enjoyable experience for every guest. Teachers learn how to communicate ideas clearly, understand different learning styles, and help people improve. These abilities transfer naturally into both sales and leadership. Cassie joined Chesapeake Homes without a real estate license or previous new home sales experience. She began selling on-site, advanced into sales management, and eventually moved into her current company-wide leadership role. Her story demonstrates an important truth: Industry experience can be helpful, but curiosity, energy, resilience, and coachability are often better predictors of long-term success.
Cassie’s leadership philosophy is heavily influenced by sports. Championship teams do not succeed through individual talent alone. Their members trust one another, understand their roles, and want to work hard for each other. That is the type of culture Cassie has intentionally cultivated at Chesapeake Homes.
She believes team members should be able to enjoy themselves while remaining focused on serious goals. Team-building activities, friendly competitions, and public recognition help salespeople stay engaged while reinforcing the behaviors that drive performance. As Cassie explained, “We’re going to be in the trenches together, and we’re going to rise together.” That statement captures her leadership style perfectly. She does not simply establish expectations from a distance. She stays involved, supports her managers, and demonstrates that leadership is a shared commitment to the team’s success.
Many sales contests only reward the final result. The salesperson with the most sales wins, even though community traffic, inventory, pricing and absorption can vary dramatically from one location to another. Cassie and Roland took a different approach by introducing the SALT Race—Sales Activities Leading to Transformation.
Rather than focusing exclusively on sales, the competition rewards the repeatable behaviors that eventually produce them. These include:
This makes the competition fairer and helps salespeople build productive habits. When Chesapeake Homes launched a 90-day SALT challenge near the end of the year, the team received points, gift cards, traveling trophies, and ultimately a cash prize. More importantly, the activities created momentum that continued into January and February, helping previously slower communities improve their results. The lasting value was not the contest itself. It was the confidence and consistency the salespeople developed along the way.
One of the most valuable lessons from the conversation concerned aged leads. New home salespeople naturally focus on their newest and most active prospects. However, many buyers take months—or even years—to make a decision, particularly when relocating, retiring, or purchasing in a lifestyle community. Cassie compared cleaning a database to organizing a closet. Some things no longer belong there, but valuable opportunities are often hidden among the clutter.
The SALT Race therefore gave additional recognition to salespeople who brought an aged lead back for another appointment—and even more points when that renewed relationship resulted in a sale. The lesson is simple: A database is only valuable when salespeople consistently and thoughtfully use it.
Cassie also encourages her team to incorporate personalized video into their customer communication. During discovery, a buyer may mention loving a particular kitchen, view, backyard, screened porch or breakfast area. A salesperson can return to that location after the visit and record a short message reminding the buyer of the moment. This is not simply another generic follow-up touch. It demonstrates that the salesperson listened.
In one memorable example, two Chesapeake Homes salespeople recorded a playful fall video, tossed leaves into the air, and wished their prospects a “Happy Fall, y’all!” The message generated numerous responses, three appointments and one sale from a database of approximately 150 people. The production did not need to be elaborate. Its power came from being personal, memorable, and authentic. We must remember that new home sales is still about human beings connecting with other human beings.
Cassie wants her salespeople to be viewed as trusted advisors rather than transactional representatives. A trusted advisor listens carefully, understands the buyer’s fears, and helps that person make a decision that genuinely supports their needs. This is especially important for buyers who are “right-sizing,” relocating or beginning a new chapter of life.
The same philosophy applies to Realtor relationships. Chesapeake Homes does not treat Realtor outreach as a temporary initiative. Its salespeople are encouraged to build consistent relationships through office visits, presentations, lunches, coffee meetings, and valuable communication. The goal is to become the Realtor’s first call when a buyer needs new home guidance—even before the Realtor knows which community or available home might be the best fit.
When Cassie entered her first full year as Director of Sales and Design, she wanted every department to understand how it contributed to the company’s sales goals. Her solution was beautifully appropriate for a homebuilder: Build the annual goal brick by brick.
Cassie created a visual house in which every new sale added another colored brick. Each of Chesapeake Homes’ divisions could be represented by a different color, allowing the entire company to watch the house take shape throughout the year. The idea quickly grew. Sales managers introduced physical LEGO houses at their meetings, adding pieces as their divisions made progress. A numerical target can sometimes feel distant or abstract. A house gradually being built creates a visible story of momentum. It reminds employees that every sale represents both a home and a family—and that every department contributes to the result.
Positive leadership does not mean avoiding accountability. Cassie introduced an accountability agreement outlining the company’s goals, standards, and expectations. Each salesperson signed it at the beginning of the year, creating a shared understanding of what success requires. When coaching is needed, managers can return to the agreement and ask, “This is what we agreed upon. How are we going to get there?” Chesapeake Homes also uses video shops and technology-assisted call evaluation as game footage. Just as an athletic coach reviews film, managers and salespeople can examine real customer interactions, recognize what went well, and identify missing steps in the sales process. This makes coaching timely, specific, and objective. It allows leaders to address a behavior before it becomes a deeply established habit.
Cassie does not believe every new hire needs years of real estate experience. With the right training systems in place, an energetic, coachable person can develop into an exceptional new home sales professional.
She shared the example of Sam Barkin, who joined Chesapeake Homes as a 19-year-old intern, entered the company’s agent-in-training program, and later earned national Rookie of the Year recognition from the National Association of Home Builders. His success illustrates what can happen when a company recognizes potential and a new professional embraces coaching, asks questions, and willingly tries new ideas. Experienced candidates can also thrive, provided they possess an open mindset. Previous success is valuable, but “This is how I have always done it” can become a barrier when the market, customer, and sales process have changed.
Chesapeake Homes’ structured recruiting process includes a written questionnaire, interviews, a behavioral assessment, and additional third-party evaluation. The questionnaire is more than paperwork. It reveals whether a candidate follows instructions, communicates effectively, responds promptly, and takes the opportunity seriously.
Changing an established sales culture is a little like turning a cruise ship: It requires patience, direction, and a series of deliberate adjustments. Cassie recommends testing major initiatives with a small group of enthusiastic, coachable team members. These early adopters can help work through challenges, demonstrate results, and become credible champions when the program expands across the organization.
She also recognizes that not every talented person is the right fit for every team. Like sports, a successful sales organization needs a mix of players who complement one another, understand their responsibilities, and support a shared standard. Culture is not built through one announcement. It is created through the behaviors leaders consistently model, coach, recognize, and protect.
Cassie closed the conversation with a message that applies to every salesperson and leader:
“Things will become difficult. There will be disappointing days, unexpected changes and moments when results do not go according to plan. What matters is learning how to reset, stand back up and continue moving forward with the right attitude.”
Cassie Smith’s journey proves that great sales leadership is not about having all the answers. It is about creating an environment where people can learn, be accountable, enjoy working together, and become better than they believed they could be. That is how sustainable success is built—one person, one habit, one relationship, and one brick at a time.
Roland Nairnsey is a highly sought-after new home sales coach and consultant and is coaching sales teams across North America with monthly sales in the billions. Roland is the author of Mastery of Selling for New Homes and Mastery of Negotiation. Roland would love to chat with you and help you with your needs.
He can be reached at Roland@newhomesaleplus.com or 561-236-2400.