KEY POINTS
- From Grit to Growth: Mike's journey from a college summer job to a multi-million-dollar sales career reveals that adaptability is the key to longevity in sales.
- The New Rules of Engagement: In the age of internet transparency, success comes not from hiding information but from providing it instantly to earn a customer's trust.
- Collaboration is Currency: You can hit your minimums on your own, but explosive, record-breaking growth is only possible when you move from a "lone wolf" to a collaborative team player.
What if your commission didn’t even start until you sold $75,000,000 this year?
That was Mike Goldenstein’s reality!
In this D2D Podcast episode, Hunter Lee sits down with Mike (now CRO at Roofle Technologies) and a seasoned B2B sales veteran with over 30 years of roofing industry experience to unpack how he scaled from $1M dreams to nine-figure targets without burning out.
The lesson: Today’s wins don’t come from hiding price or muscling through alone; they come from speed, transparency, and collaboration.
Mike also shares his powerful journey from installer to corporate leader and offers a playbook that can help teams thrive in a sales culture defined by transparency and trust.
If your prospects seem to be a step ahead of your team’s script, this conversation will show how to turn their tech-savviness into your edge—earning trust fast, getting to the kitchen table quicker, and compounding results with a team that complements your strengths.
Watch the full breakdown on the D2D Experts YouTube channel, or keep reading for Mike’s field-tested system.
Watch / Listen
Guest: Mike Goldenstein, CRO of Roofle Technologies.
The New Rules of Sales: Creativity, Collaboration, and Long-Term Vision
Mike’s career began with him hand-nailing shingles in 1992 and evolved into a B2B role with GAF, North America’s largest roofing manufacturer. His targets climbed from $1 million to over $75 million annually, a transition he credits to a mindset shift from a solo operator to a collaborative leader.
1. A New Philosophy: Always Be Creating
Mike believes the old sales mantra of “always be closing” is obsolete. He’s a proponent of “always be creating”. He emphasizes that high performers are motivated not by money, but by creativity, preparation, and attention to detail. This approach helped him move past price wars and start winning with solutions. For example, he figured out that his storm-restoration competitors weren’t winning on price but by creatively providing solutions his customers actually needed.
2. The Power of Collaboration
When Mike’s team was stuck, they shifted from individual “lone wolf” tactics to a collaborative “three-leg stool” approach. By having one person focus on storm restoration, another on multi-family projects, and a third on retail, they leaned on each other’s strengths and ended up tripling their market share. This proves that while you can hit your minimums on your own, explosive growth comes from teamwork.
3. The Long-Term Mindset
When a rep is in a slump, it’s easy to panic. Mike’s advice: “have a long-term vision”. He compares it to pushing a boulder; when the terrain changes, you can’t just push harder. You have to change your approach and understand that future, explosive growth is the result of a “long obedience in a long direction”.
Adapting to the Modern Buyer
The internet has fundamentally changed customer behavior. Today’s buyer is tech-savvy and expects transparency. Refusing to give an instant quote, for example, can be seen as a sign that you’re hiding something, which immediately breaks trust.
Mike highlights this with a story about his nine-year-old son, who, after being told who the greatest NFL running back was, immediately pulled out his phone to verify the information with Siri. This simple interaction is a powerful lesson: modern buyers can, and will, verify everything you say. The instant you leave their door, they’re looking you up.
This is where Roofle comes in. It’s a “bolt-on” technology that helps you earn the right to get to the kitchen table. Instead of refusing to provide a quote, you can put the homeowner’s address into the app and get instant, detailed, and accurate estimates on a variety of products. This transparency builds trust and equips you to sell to modern buyers.
A Checklist for the Modern Sales Rep
- Become a problem-solver. Stop asking about a customer’s pain points—you already know what they are. Instead, start the conversation by asking how they are resolving those problems.
- Embrace transparency. The “always be closing” era is over. Give the customer the information they need when they need it, even if that feels like a loss of control.
- Build trust with data. Leverage technology to provide instant, verifiable information. Your expertise is validated when you can back up your claims with transparent data.
- Don’t rely on solo heroics. Learn your weaknesses and lean on your team’s strengths. Collaboration is the key to scaling past your own limitations.
Hire fewer trainers, ship more wins
Build a sales machine that runs without you hovering
Albert Brand boasts over a decade of expertise in the telecommunications industry, with a particular emphasis on fiber optics sales. His rich career spans both corporate roles and entrepreneurial ventures in sales fulfillment. With a proven track record in door-to-door sales, especially in the fiber optics domain, Albert has seamlessly bridged the gap between corporate leadership and hands-on sales, showcasing his versatility and commitment to excellence in this specialized field.
