Skip to main content

Success Story

Optimizing Lead Follow Up in Real Estate with AI

Jeffrey Chubb

How one Realtor increased conversions without increasing headcount

Jeffrey Chubb of Chubb Homes Team leads a team of six. The agency structure is strategic, having scaled back from a 25-person headcount a few years ago to allow for more agility in the competitive Boston metropolitan market. The sixth member of the team is not, in fact, a person at all. She’s a virtual assistant powered by artificial intelligence (AI), and she has the highest lead engagement rates on the team.

While the agency Chubb operates has consistently ranked as one of the top real estate teams in the state of Massachusetts, he saw a need for improving lead follow up, so he implemented a conversational AI tool in 2017.

“As we worked with Sierra Interactive’s lead generation platform, we became so effective at pulling in quality leads that, as a small team, I knew we couldn’t sustain a response time that met my agency’s high standards,” he said.

Knowing quality leads have a higher potential to convert to revenue, Chubb wanted to find a solution to keep leads from falling through the cracks.

“Generally speaking, there were only two options: increasing agency headcount to absorb the responsibilities of follow up, or finding a technology solution that could take on the follow up for us,” Chubb explained. “While either solution could have worked, only one would give my agents more time to do what they do best while still supporting our goal of agility.”

A fix for lead follow-up on a small, agile team.

“In any market, follow up is a demanding requirement for even the most engaged agents,” said Chubb. “For agents to be able to focus their time on high-value activities and close deals, they need to be able to let go of some of the lower value tasks. While general lead follow-up is necessary, it can too often bog agents down in non-revenue-driving efforts.”

As his business grew, it became increasingly difficult for Chubb’s team to spend their time on the countless hours that effective follow up required.

“It takes several contacts with a prospect to convert them in any way,” said Chubb. “Multiply that across all lead volume, and that level of lead engagement amounts to manual follow up and, quite possibly, burnout,” said Chubb. “Realistically, a team as busy as mine couldn’t be expected to manage all aspects of their work and continue to respond quickly to new leads as we generated them. I wanted to empower my agents to refocus their priorities towards the high value aspects of their work: the open houses, the showings, the touchpoints with transaction-ready leads and clients. Still, I didn’t want our quality of service or response times to lag as a result of shifting priorities.”

It was a challenge Chubb needed to solve, preferably without adding headcount (and overhead) to his team as he strategically scaled down.

“I needed a system in place that could fill the cracks in follow up before we could even identify a gap,” said Chubb.

Chubb turned to a conversational AI tool that could respond to and qualify leads through consistent engagement.

Introducing Valerie, the sixth member of the team.

While Chubb saw the potential in launching AI as a part of his business strategy, he didn’t want his clients to feel like they were losing the human relationships his team valued so highly. After Chubb launched the automated assistant, he quickly validated the authenticity of each conversation, and connection, fostered using Sierra AI.

“The AI tool Sierra offers is so realistic, we named ours ‘Valerie Miller’ and even created an email address for her. If and when our agents jump in midway through follow up, they refer to Valerie as their assistant.

“Our leads often don’t realize they’re not interacting with an actual person.”

“Valerie can communicate with empathy to our leads. She can handle objections as they come up, answer questions, and automatically route the right lead to the right agent at the right time.”

Another Introduction: Sierra AI

Back in 2017, Chubb was a very early adopter of AI technology in real estate. Now, AI is much more mainstream and demand for it has increased. Real estate pros like Chubb recognize the useful, practical ways AI can bring value to their business from speed to lead to higher conversions to reducing the need for additional headcount. One drawback, though, has been that often the AI tool is only very loosely integrated, if at all, with the operations hub of a real estate business – the CRM.

With Sierra AI, the conversational AI tool is fully integrated with Sierra’s CRM, so agents get a full picture of lead conversations and activities. Not to mention features like lead routing can be used alongside and as part of a holistic lead follow up system. In this way, Sierra AI can truly become a part of the team, like an agent working out of the CRM. “At Sierra Interactive, we’re always looking for ways to help our clients maximize efficiencies and close more deals,” said David Short, Head of Product at Sierra. “Sierra AI is a prime example of that goal. By aligning AI with our powerful lead routing logic, our clients can nurture and qualify new leads until an agent chooses to – or is able to – step into the conversation.”

Industry research reports half of all sales efforts require at least five or more touch points before closing a sale. Multiplied across all leads (and all agents) that kind of dedication to follow up amounts to a huge investment of resources.

Sierra AI helps in two ways:

1. By automatically attempting to re-engage dormant leads over a period of time.
2. Reducing response time on hot leads to engage and qualify them immediately.

For older leads, Sierra AI maintains a consistent cadence of follow up, providing an average of 25 touchpoints over a year to ensure you’re there at just the right time when a lead is ready to engage. When a lead engages in conversation, Sierra AI can adapt to context and evolve the conversation using compassion and integrity, just as your agents would, using data gathered from millions of conversations.

“Relationships are so important in the real estate business,” Short agreed. “We’ve all interacted with a chatbot in some way, shape or form before, and we know how frustrating it can be when it feels like you’re only talking to a computer. It was really important that our clients never felt like they were losing the human connection with their clients and prospective clients. Using an empathetic and tailored approach to every conversation, Sierra AI fosters human connections, in most cases to the point that the audience doesn’t even realize they’re talking to AI.”

Real relationships. Real results.

Within five months of ‘onboarding’ Valerie, Chubb’s agency engaged and qualified over 500 leads. Now, Valerie has been a part of his team for more than six years, and as the AI becomes more seamlessly integrated with Sierra’s real estate CRM and lead generation solutions, he couldn’t imagine it any other way.

“The consistency of Valerie [our AI virtual assistant] is of immense value to my agents and our team. Often, even when a lead is initially silent, Valerie can solicit a response. Even if they hadn’t responded to any of the first follow up efforts and three months have gone by, Valerie can deliver a response. That kind of consistency is something we couldn’t scale without the help of AI.”

Today, Valerie offers the highest lead engagement rates on the team, and Chubb has seen a significant number of conversions lead to closed deals.

“It’s really an invaluable tool regardless of agency size,” Chubb explained. “If I chose to operate a larger team, lead flow can improve and increase conversions just as effectively as how we use it to support our smaller team. Whether you’re working through ten leads a month or a thousand, AI is a tangible solution for bettering follow up, qualifying leads and increasing conversions.”


Sierra Interactive develops residential real estate software and services for agents, teams and brokers in the U.S. and Canada. Sierra’s proven lead generation and management solutions are trusted by top-performing teams and influential coaches in the real estate industry. Founded in 2007, Sierra is headquartered in Louisville, KY, but has a remote-first workforce across the U.S.

Care to share? Download the free PDF file and send to your network today.

Download Now

Schedule a Demo

Thoughtfully designed features, intuitive workflows and stunning UX. You’re about to find out why top-performing real estate teams pick Sierra.

Sign Up