Brad Hargreaves knows how to build and sell. As an entrepreneur at the intersection of real estate and technology, he launched and sold two major companies—General Assembly and Common. Now, through his company, ThesisDriven, he helps real estate and proptech founders refine their value propositions to close deals faster and win bigger. His insights into selling to real estate owners help sales teams move beyond "maybe" to a definitive "Hell Yes!"Brad’s background gives him a unique perspective on selling innovative solutions in real estate. From founding and scaling businesses to selling them successfully, he understands what it takes to articulate value in a way that resonates with skeptical and conservative buyers.Selling to real estate owners, operators, and managers isn’t straightforward. The industry has long decision cycles and deeply ingrained processes. Brad points out that the biggest roadblock isn’t competition—it’s inertia. Many buyers resist change simply because they’ve “always done it this way.” Add in veto holders, lender skepticism, and a failure to articulate value clearly, and sales stall quickly.Many proptech companies make the mistake of targeting big players—REITs, large institutional owners, and well-funded developers. These organizations may talk about industry trends, but they have long sales cycles and complex decision-making processes. Instead, Brad emphasizes the importance of identifying Hell Yes buyers—those who see the problem and actively seek a solution.To succeed in selling to real estate owners, founders and sales teams must understand their ecosystem. Multiple decision-makers exist, each with different priorities. The financial structure of real estate ownership also presents challenges. Investors, lenders, and property managers all influence whether a company adopts a new technology or solution.The key to getting to “Hell Yes” isn’t about pushing harder; it’s about understanding the buyer. Brad teaches a few critical strategies for breaking through:
Listen to the “Getting to Hell Yes!” podcast on apple or spotify here:https://open.spotify.com/show/4TY87ToVuLK7eqkZZvZA5Thttps://podcasts.apple.com/gm/podcast/getting-to-hell-yes/id1772602174
1. Speak the Language of Real Estate
One of the biggest barriers to selling proptech solutions is a disconnect in language. Tech founders focus on features, but real estate owners care about NOI (Net Operating Income), risk mitigation, and operational efficiency. If a seller can’t articulate value in these terms, they won’t gain traction.“If you can’t speak their language, you can’t sell to them,” Brad advises. Understanding how different asset classes operate, how deals work, and what financing mechanisms exist makes the difference between a compelling pitch and a confusing one.2. Find the Right Champion
In complex sales cycles, the person experiencing the problem isn’t always the decision-maker. The VP of Asset Management might struggle with operational inefficiencies, but the Managing Director or Principal holds the budget. Successful sales teams find their internal champion—the person motivated to solve the problem—and equip them with tools to advocate internally.“You’re not just selling to the buyer—you’re equipping them to sell for you,” Brad highlights. Real estate decision-makers rely on numbers, so providing concrete proof of value is crucial.3. Discover (Not Create) Time Walls
Unlike in consumer sales, where urgency tactics like limited-time discounts work, real estate follows its own cycles. “Real estate operates on its own cycles. Find them and align your pitch accordingly,” Brad explains.For example, upcoming refinancing events, budget planning cycles, or lease-up periods create natural decision points where decision-makers act. Understanding these cycles allows sellers to position their offering at the right time.By shifting their approach, proptech founders can avoid “pilot hell” and close deals with the right buyers. Brad’s approach helps sellers align their efforts with decision-makers ready to say yes. His Selling into Real Estate Owners course builds on these lessons, ensuring participants learn how to:- Identify the right prospects—not just the most visible ones.
- Structure sales conversations around real estate priorities, not just tech features.
- Generate leads and scale sales using tested frameworks.
- Empathy is Everything – Successful sales start by understanding the buyer’s world, pressures, and goals. Real estate professionals don’t just buy technology; they solve operational challenges, manage risk, and optimize investments. Sales teams who approach conversations with curiosity and empathy go further.
- The Right Buyer is Key – Don’t waste time chasing prospects who show interest but move slowly. Instead, find scrappy, growing owner-operators who need a solution now and can make quick decisions. These buyers drive adoption and advocate for new solutions.
- Sales is a Process, Not a Pitch – Many PropTech companies struggle because they treat sales as a one-time pitch. In reality, selling to real estate owners requires discovery, iteration, and alignment. The best sales teams engage in ongoing dialogue, refining their approach based on buyer feedback.
Listen to the “Getting to Hell Yes!” podcast on apple or spotify here:https://open.spotify.com/show/4TY87ToVuLK7eqkZZvZA5Thttps://podcasts.apple.com/gm/podcast/getting-to-hell-yes/id1772602174
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