There’s no way to sugarcoat this: Adopting AI inside your organization can be so dang hard. Teams need to change how they work, leaders need to prove the investment is paying off, and someone has to own what happens after launch.
That’s why we’re excited to cultivate more honest, intimate conversations, whether around a dinner table or one-on-one. Hearing how peers are working through those challenges can make your own path clearer.
At our AI Executive Dinner in Scottsdale this October, five executives shared what builds their AI confidence to move forward: visibility, a clear plan, accountability, and measurable ROI.
AI Headlines Change Every Week and Operators Need Answers
Nurture Boss hosted the AI Executive Dinner to help multifamily leaders make sense of recent AI headlines and connect them to decisions inside their organizations.
We brought our expertise, but the conversation started with their concerns. We asked each executive the same question: What would make you feel comfortable rolling out AI across your organization?
Their answers outlined what it takes to move forward with confidence. For Natalie Cariola, Chief Revenue Officer at SmartRent, confidence starts with knowing when something goes wrong.
“How do I know if my AI agent has gone rogue, and how do I learn about it before I learn the hard way?”
Operators would never ask a new leasing agent to handle every prospect conversation without reviewing their work. AI deserves the same scrutiny. That means access to the conversations AI handles, clear alerts when a person needs to step in, and a straightforward way to take over. An operator should be able to spot an issue and address it before a resident has to escalate it.
Visibility makes oversight possible. It also gives leaders evidence that their AI is doing the job they expect.
What Is the Right Order for an AI Rollout?
Patrick Antrim, Chairman of the Multifamily Innovation® Council and Founder and CEO of nectarflow®, laid out a five-step sequence.
“First, I need to know: Do I have the right team together? With the right people in place, we can identify the right problem to solve. From there, I want to understand the data. Once those pieces are clear, I’m ready to pick a tool. The final step is executive execution.”
His order is important:
- Build the right team
- Identify the right problem to solve
- Understand the data
- Pick the tool
- Drive executive execution
The tool comes fourth.
Starting with software leaves teams trying to fit their operations around a purchase. Starting with people, a defined problem, and an understanding of the data gives the technology a clear purpose.
Executive execution then turns that plan into an operating commitment: someone owns the rollout, teams know what success looks like, and leadership stays involved after launch.
How Should AI Support Onsite Teams’ Judgment?
Kyle Shipp, Managing Director of Digital Products and Services at RPM Living, drew a clear line between helping people work and letting technology think for them.
“I would want to see more people leveraging the power of AI to amplify their skills. I don’t want people to outsource their taste or critical thinking.”
Speed alone is an incomplete measure of success. Teams also need to recognize when an answer misses the context, when a resident needs a more personal response, and when an exception requires human judgment.
AI can handle routine questions, draft follow-ups, schedule tours, answer ledger balance questions, and keep conversations moving after hours. Leasing professionals bring the expert knowledge of their communities and build stronger resident relationships.
That reflects Nurture Boss’s approach: human-led first, AI-powered second.
Who Is Accountable for AI after Launch?
Windell Mollenido, VP of Marketing and Technology at The REMM Group, challenged the assumption that implementation ends at activation.
“It’s important for me to see a level of accountability folks give to AI. We assume it’s a set it and forget it tool and that it’ll take the job and run with it. There needs to be a level of AI governance.”
Governance needs to answer practical questions. Who reviews AI conversations? When should AI hand off to a person? Who updates its instructions when policies change? Who is responsible when performance falls short?
Those responsibilities need named owners and a regular review process. Teams also need control over follow-up timing, escalation rules, and when to pause AI so a person can lead.
A successful launch establishes those expectations. Ongoing accountability keeps them relevant as the portfolio changes.
How Should Operators Measure the ROI of AI?
We also asked: What about AI do you wish you could get a straight answer to?
Robert Hicks, Jr., Division President, West at Asset Living, brought the conversation back to financial value:
“How much money will it save me?”
The answer needs more substance than message volume or a list of automated tasks. Operators need to understand which outcomes AI supports, what those outcomes are worth, and how that value compares with the investment.
AI should prove its value through higher net operating income, influenced leases, fewer vacancy days, reduced delinquency, and stronger renewal rates. Establishing a baseline before launch helps separate AI’s contribution from changes in market conditions and portfolio performance.
What Gives Multifamily Leaders Confidence to Move Forward?
Across the conversation, five requirements emerged:
- Visibility: Access to AI conversations and a clear way to intervene.
- A clear plan: The right people, a defined problem, and an understanding of the data before selecting software.
- Human judgment: Teams that use AI while continuing to think critically.
- Accountability: Named owners, operating rules, and ongoing review.
- Measurable ROI: Results tied to business outcomes, with clear attribution.
These intimate conversations are important because they turn broad concerns about AI into specific requirements operators can act on. That can happen around a dinner table or in a one-on-one conversation about a challenge inside a single community.
Nurture Boss will host more AI Executive Dinners in 2027 to keep those conversations moving. Our role is to bring expertise, listen closely, and help operators turn what they learn into a clear next step.
