In the world of selling, closing a deal isn’t just about persuading—it’s about connecting, understanding, and providing solutions that truly matter to your customers. This drive defines Dennis Bron, a seasoned professional whose career spans McKinsey, Better.com, and now Roofstock. Dennis wears many hats: growth leader, operations expert, and innovator in the property management space. His unique perspective shows how sales dynamics evolve and what it takes to achieve the coveted "Hell Yes!" from customers.Dennis offers invaluable lessons about navigating today’s sales landscape. Here, we unpack his insights through four themes: setting, complication, turning point, and resolution.
Dennis Bron’s journey offers a powerful blueprint for navigating modern sales. By focusing on problem-solving, personalization, and continuous innovation, sellers move beyond transactional interactions to build meaningful, trust-driven relationships.In an era where buyers are more informed and discerning than ever, the “Hell Yes!” approach isn’t just a strategy—it’s a necessity. By embracing Dennis’ principles, you can exceed customer expectations and create lasting partnerships that drive success for everyone involved.Next time you’re working to close a deal, ask yourself: Are you selling, or are you solving? The answer could make all the difference in getting to “Hell Yes!”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
Setting: A Career Rooted in Growth and Change
Dennis started at McKinsey, sharpening his problem-solving and strategic thinking skills. Over the years, he took on roles in tech-enabled ventures like Better.com and Shift.com, gaining firsthand experience in industries such as online mortgages and used car sales. These roles solidified his expertise in growth strategies and emphasized the importance of adapting to changing markets.In his current role at Roofstock, a platform for property management and single-family rental (SFR) investments, Dennis leads the charge in delivering high-quality, tech-driven services. He focuses on data transparency and customer-centric solutions, bridging the gap between institutional investors and everyday property owners.“We’re selling trust,” Dennis explains. In industries where trust is currency—whether managing investment properties or building customer relationships—this principle drives his approach.The Shift from Persuasion to Problem-Solving
The sales landscape has transformed dramatically. “We’ve moved from a world of persuasion to a world of problem-solving,” Dennis says. Today’s buyers are savvy, informed, and discerning. They don’t just want products or services; they want partners who understand their challenges and offer tailored solutions.In property management, this shift is particularly pronounced. Economic fluctuations have changed investor priorities. “We went from an industry that was growing super fast to one where the market is shrinking. Investors are net sellers, and we’re competing for a smaller group of buyers with evolving needs,” Dennis shares.This reality demands a new sales mindset. Sellers must move beyond pushing products to becoming advisors who help buyers identify their problems and align on solutions that deliver real value. For Dennis, this means prioritizing consistency, professionalism, and a deep understanding of the customer journey.Getting to “Hell Yes!”
At the heart of Dennis’ philosophy is a fundamental shift in how sales teams work. To get to “Hell Yes!” with customers, you master three critical phases:- Needs Discovery Understand what your customer truly needs. This means actively listening and asking the right questions to uncover pain points.
“You can’t sell a solution if you don’t know the problem,” Dennis says. Whether it’s an institutional investor managing a property portfolio or a landlord with two rental homes, success starts with meeting them where they are. - Building Value: Once you understand the needs, show how your product or service addresses them. For Dennis, simplicity is key.
“Early in the process, you pique people’s interest with simple, clear messaging. As they move further along, you build on that foundation with more detailed information,” he says. - Closing the Deal: This phase turns trust and value alignment into action. Dennis rejects the traditional “always be closing” mantra. “There’s a lot of courtship that should come before closing,” he notes. When you focus on understanding and value, closing becomes a natural conclusion rather than a forced transaction.
Innovating and Iterating for Success
The solution to modern sales challenges lies in innovation and iteration. Dennis likens Roofstock’s approach to “flying the plane while building it.”“You can’t incubate an idea in isolation and hope it lands in the market. You iterate in real time, learn from customer feedback, and refine as you go,” he explains.This approach ensures Roofstock’s offerings align with customer needs. By combining tech-driven solutions with a focus on human connection, the company sets a new standard for property management and SFR investments. Through AI-powered chatbots, real-time data analytics, and robust maintenance platforms, Dennis and his team redefine exceptional service.The goal is to make every customer interaction a “Hell Yes!” moment. For Dennis, that means building trust, offering value, and always centering the customer.Key Takeaways: Lessons for Getting to Hell Yes!
Here are three actionable takeaways from Dennis’ insights for sellers across industries:- Understand Before Selling: Needs discovery is the foundation of effective selling. Listening and adapting to customer challenges make it easier to build trust and show value.
- Simplicity Drives Interest: Clear, simple messaging cuts through the noise. Whether it’s an ad, a sales pitch, or a follow-up email, keep communication concise and focused on solving the buyer’s problem.
- Embrace Personalization: Treat every customer as unique. Adaptive marketing and sales strategies that cater to individual preferences outperform one-size-fits-all approaches. Use technology to deliver tailored experiences and build lasting relationships.
Dennis Bron’s journey offers a powerful blueprint for navigating modern sales. By focusing on problem-solving, personalization, and continuous innovation, sellers move beyond transactional interactions to build meaningful, trust-driven relationships.In an era where buyers are more informed and discerning than ever, the “Hell Yes!” approach isn’t just a strategy—it’s a necessity. By embracing Dennis’ principles, you can exceed customer expectations and create lasting partnerships that drive success for everyone involved.Next time you’re working to close a deal, ask yourself: Are you selling, or are you solving? The answer could make all the difference in getting to “Hell Yes!”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
Our mission is to simplify the homeowners & home builders customer experience. Let Iris do the work.
Up next
Getting to Hell Yes! in Selling: Insights from Dennis Steigerwalt
By: Guillermo Salazar • 12 January 2025
Dennis Steigerwalt: Driving Housing Innovation with Vision, Collaboration, and 'Hell Yes!' Solutions
The importance of online product reviews [+3 ways to get more]
By: IrisCX • 19 September 2022
Online reviews are impactful because they reach people with purchasing intent – a total of 93% of new customers consult reviews before purchasing a product or service. With virtual CX, your team can start receiving and leveraging better quality reviews.
Building Value: How New Home Builders Save Big with a Stellar Customer Experience Strategy
By: Guillermo Salazar • 08 January 2024
7 ways to measure your CX program in New Home building