The Journey to Leadership and Selling with Purpose
David Shaw, President and COO of Lively, didn’t follow a traditional career path into multifamily or proptech. He started in Minneapolis, where he worked at Best Buy and Starbucks, gaining experience in customer experience and business strategy. His time at these companies shaped his leadership and sales approach.Shaw learned that selling isn’t about offering a product—it’s about solving real problems. When he moved into the startup world, particularly in real estate and proptech, he saw a gap in how resident experience was managed. Property managers used multiple tools, but many solutions weren’t fully adopted. As a result, site teams wasted time, employees grew frustrated, and operations remained inefficient.At Lively, Shaw saw a chance to change the game. By focusing on efficiency, engagement, and resident experience, Lively provided a technology-driven solution that streamlined operations and improved the overall experience for both property teams and tenants. But convincing decision-makers to embrace change posed a challenge.The Common Challenges in Selling Change
Selling in multifamily presents unique obstacles. Even when a product delivers value, getting buy-in from property management companies, operators, and stakeholders is another challenge. Shaw and his team faced three primary hurdles:1. Fear of Change Management
Property managers and site teams already juggle multiple responsibilities. Adding another platform—even one that simplifies their work—feels overwhelming. They worry about learning new systems, onboarding staff, and whether employees will actually use it.2. Market Confusion
With countless proptech solutions available, decision-makers feel lost in a sea of options. Every software promises efficiency and better resident engagement, but many fail to deliver real ROI. Operators hesitate, unsure of which solution truly fits their needs.3. Lack of Urgency
Unlike urgent repairs or high-priority vacancies, improving resident experience doesn’t always seem pressing. Operators put it off, not realizing its long-term impact on retention, revenue, and efficiency.To close deals, Shaw had to help prospects see the problem differently.The 'Hell Yes!' Moment
So, how does a hesitant “maybe” turn into an enthusiastic “Hell Yes!”?Shaw and his team developed a simple but powerful framework: Connect, Discover, Respond.1. Connect – Build Real Relationships
Traditional sales tactics—generic cold emails and scripted pitches—don’t work. Instead, the key lies in genuine relationships.“Humans want to do business with humans,” Shaw says. Instead of mass-emailing prospects, his team engages decision-makers in real conversations by reaching out personally, attending industry events, and using LinkedIn to foster connections.2. Discover – Ask the Right Questions
Many salespeople assume they know the customer’s problem before asking. Instead, Shaw’s team lets the customer tell them.They ask questions like:- What are your site teams’ biggest frustrations?
- How do you measure resident satisfaction?
- What tools have you tried before, and why didn’t they work?
3. Respond – Offer Tailored Solutions
Once they uncover the real problems, Lively doesn’t push a one-size-fits-all solution. Instead, they deliver a customized response that directly addresses the client’s pain points.For example, if employee burnout is the issue, Lively highlights automation features that free up site teams. If low resident engagement is the concern, they showcase tools that build community and boost retention.This approach moves prospects from skepticism to conviction—leading to their “Hell Yes!” moment.Scaling Sales the Right Way
Winning a customer is just the beginning. Lively doesn’t just sell a product; they partner with customers for long-term success.Commitment to Change Management
Many prospects worry about implementing a new system. To ease this transition, Lively provides white-glove onboarding, dedicated customer success managers, and ongoing support.“We don’t just sell a product—we help customers implement and maximize it,” Shaw explains. By offering hands-on training, regular check-ins, and strategic guidance, Lively ensures that customers adopt the platform and see real results.A Revenue-Driven Approach to Customer Experience
One of the biggest takeaways from Shaw’s sales approach is the idea that resident experience is revenue experience.Operators often see resident engagement initiatives—events, communication tools, and community-building efforts—as extras. In reality, they directly impact retention and profitability.Shaw explains that retaining a resident is far more profitable than acquiring a new one. High turnover leads to increased vacancy loss, higher marketing costs, and more strain on site teams. A seamless and enjoyable resident experience reduces churn and increases profits.Key Takeaways on ‘Getting to Hell Yes!’**
1. Selling isn’t about pushing—it’s about guiding.
Great salespeople don’t force products on customers. Instead, they lead prospects toward realization by asking the right questions and offering relevant solutions.2. Customer experience drives revenue.
Retention directly impacts profitability. Investing in resident experience isn’t just a feel-good initiative—it’s a smart business move that reduces turnover and increases asset value.3. Technology should simplify, not complicate.
The best solutions make life easier for site teams and residents. Selling a new system means focusing on how it removes friction, saves time, and delivers measurable ROI.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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