From “Eating Your Veggies” to “Getting to Hell Yes!” — How Data Unlocks Real Momentum in Property Management

Why the Path to AI-Powered Property Management Starts with the Unsexy Work of Data Integrity—and How Kevin Shtofman Gets Operators to Say “Hell Yes” Anyway

A Veteran Voice in a Data-Challenged Industry

Meet Kevin Shtofman, Head of Innovation at Cherre, a real estate data integration platform that solves one of the industry’s most persistent and costly challenges: bad data. With 21 years of experience across consulting, financial analysis, and proptech leadership, Kevin understands the complexities of real estate operations.

He’s worked on both sides of the table, helping institutional investors visualize portfolios and guiding property managers toward smarter workflows. What drew him to Cherre? A deceptively simple problem: no one trusts their data.

“How do I know this unit count is accurate?” “Can I trust this occupancy rate?” These weren’t fringe cases—they were daily frustrations. Dashboards looked sleek, but under the hood? Garbage in, garbage out.

“If property owners, managers, and their systems speak different languages, you’re going to misfire every time,” Kevin says.

Kevin knew the solution meant starting at the source. Property owners, managers, and their tech tools often speak different languages. If they can’t align, nothing meaningful follows. Cherre stepped in to translate, bringing disparate systems into one standardized model.

The ‘Veggies Problem’ of Data Harmonization

Everyone knows data hygiene matters. But investing in it? That feels like “eating your Veggies”—a healthy habit everyone skips for more urgent tasks.

Data harmonization rarely makes the top-three priority list for the quarter. It’s not flashy. It lacks direct consumer-facing ROI. And it’s hard to quantify. But ignore it, and the pain piles up fast.

“Data quality isn’t an immediate fire, which is why people let it smolder,” Kevin points out.

Kevin spells it out:

  • Acquisitions teams miss reliable comps and fail to submit bids on time.
  • Property managers struggle to report to multiple owners using different systems.
  • Maintenance teams stay reactive because the data doesn’t help them act proactively.
  • Teams burn out from repetitive manual tasks, leading to high turnover.

The problem compounds. As companies grow from 2,000 to 5,000 units, manageable chaos turns unmanageable. That final 20% of bad data causes 80% of operational drag.

Company culture often amplifies the problem. Teams that don’t prioritize clean, accurate data find themselves stuck in a reactive loop. And innovation doesn’t thrive in reactive mode.

The F1 Metaphor, AI, and the Moment of Realization

Then came AI.

In early 2023, the industry discovered the power of generative tools like ChatGPT. Initially, people marveled at the speed of answers. But quickly, they realized speed didn’t equal accuracy.

“I got speed, but I didn’t get accuracy or security,” Kevin says. That’s when the real value of clean, trustworthy data clicked. AI without good data? It’s like strapping a jet engine to a tricycle.

Kevin uses a vivid metaphor:

  • The data warehouse is your engine
  • Validation rules are your steering wheel
  • Governance and access control act as your brake pedal
  • When the entire team pushes the gas together, you win the race

“Without proper data, AI just gets you lost faster,” he adds.

Winning in proptech requires speed, safety, and direction. That balance allows companies to scale without breaking.

At Cherre, that insight led to a strategic pivot. Instead of competing with internal tech teams, they partnered with them. Cherre enabled the teams to unify their data and supported executives in making strategic decisions.

Trust, Growth, and Getting to Hell Yes!

Selling data tools takes patience. It’s not about clever pitches. It’s about trust.

As head of innovation, Kevin doesn’t carry a sales quota. He doesn’t cold-call or push demos. Instead, he helps. He shows up as a partner, an advisor, and often, a friend. When buyers get ready, they turn to him.

“Helping always sells,” Kevin says. He knows most Cherre customers didn’t sign up after a first conversation. Often, it took years of advice, conference meetings, and helpful nudges before a deal emerged.

“If you show up to help before you’re asked to sell, the trust builds naturally,” he explains.

So when do people buy?

  1. They’re growing and realize their systems can’t scale.
  2. They hit a wall, like a loan refi or insurance audit.
  3. Leadership demands clarity, and no one has the answers.

In those moments, Cherre isn’t just another vendor. It’s the partner that already earned trust.

Kevin emphasizes what every buyer wants:

  • Increase revenue
  • Reduce cost
  • Reduce risk

Ideally, a solution does all three. But it must at least do one.

And here’s the hidden gold: speed. If Cherre cuts decision time from 72 hours to 5 minutes, companies speed up month-end closes, make decisions faster, and gain confidence.

“Speed without accuracy is chaos. Speed with control? That’s how you scale,” Kevin says.

Imagine making 220 decisions a year instead of 12. That kind of transformation creates “Hell Yes” moments in the C-suite.

Getting to Hell Yes! in Selling

  1. Be the F1 Crew Chief, Not the Engine Salesman Show how your solution makes the entire machine run faster and smarter. It’s not about features—it’s about results.
  2. Slow is Smooth, Smooth is Fast Kevin learned to listen more, multitask less, and stay present. When you focus fully, you understand what buyers truly need.
  3. Trust Is the Real Close The sale happens long before the contract. Build a reputation as a helpful, trusted partner.

What Real Estate Needs Now

Kevin’s insights reflect a bigger shift. Real estate is moving beyond siloed data, manual tasks, and reactive choices. It’s heading toward standardization, automation, and smart strategies.

But adoption depends on culture. And culture needs champions like Kevin—people who face tough data challenges, eat their Veggies, and guide companies toward meaningful growth.

“Doing nothing is the most expensive option of all,” Kevin notes.

Because doing nothing? That costs real money. Missed deals. Wasted hours. Broken trust.

In today’s economy, where speed and efficiency rule, those who build a strong data foundation today win the race tomorrow.

So what’s stopping you from reaching your “Hell Yes” moment?

Need help getting to ‘Hell Yes’? Start by asking better questions, showing up as a guide, and focusing on outcomes that matter. Kevin’s playbook may not be flashy—but it’s what makes the best sellers unstoppable.

And maybe, just maybe, it’s time we all ate our Veggies.

Want regular insight & stories on how to Get to Hell Yes? Follow us on LinkedIn here: https://www.linkedin.com/in/1guillermosalazar

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