Selling in today’s multifamily market is tough. The old tactics? They don’t work anymore. Buyers expect more, budgets are tight, and there are more decision-makers at the table than ever before.

But for sales leaders like Mike Wolber, Chief Revenue Officer at Apartment List, this challenge is an opportunity. His secret? It’s not just about selling. It’s about getting customers to say: “Hell Yes!”

Here’s how Mike does it.

A career built on bold moves

Mike didn’t start in real estate. His career began at Nike, where he worked on product creation. But even at a company like Nike, he felt like a number—a cog in a giant machine. So, he made a bold move: he left.

He and his wife packed up and moved to Bend, Oregon, choosing happiness over corporate hierarchy. That decision set the stage for an incredible journey. In Bend, Mike discovered the multifamily world, joined G5, and fell in love with the fast-paced, high-growth world of PropTech.

From there, he helped scale Rent Dynamics, sold it to Entrada, and eventually became Chief Revenue Officer at Apartment List, where he leads sales today.

Apartment List isn’t your typical Internet Listing Service (ILS). Instead of charging a flat fee to list properties, it operates like a two-sided marketplace—connecting renters with properties and charging only when leases are signed. Think Airbnb for apartments.

For Mike, this is the perfect arena. He’s not just hitting sales goals—he’s teaching his team to think big, visualize big, and play to win every single day.

The rules of selling have changed

Selling used to feel easy. Demand was high, deals flowed in, and sales cycles felt fast. If you had a building, you could lease it. Buyers said yes to almost everything.

Not anymore.

Today, the market demands more:

• Budgets are tight
• Decision-making committees are bigger and more complex
• Status quo is the biggest competitor in the room

Mike puts it plainly:

“If you can’t define the Cost of Inaction (COI), you’re not selling. You’re just talking.”

The real challenge? Most customers don’t know how to buy. They’re overwhelmed, unsure of the process, and need a guide. The salespeople who win aren’t just pitching—they’re teaching.

The ‘Getting to Hell Yes!’ playbook

Breaking through the noise and landing a “Hell Yes!” requires a clear, disciplined approach. Mike lays it out like this:

Teach customers how to buy

Don’t assume buyers know the process. They probably don’t.

“Your buyer likely doesn’t know how to navigate today’s complex sales process. Be their guide.”

Mike’s team walks customers through every step:

• Who needs to be in the room?
• What’s the process from pilot to full rollout?
• How do approvals work?

Helping customers navigate the buying journey builds trust, removes friction, and speeds up deals.

Capture and create urgency

Great discovery calls aren’t one-and-done. Mike calls it discernment—listening deeply, understanding priorities, and using that knowledge to move deals forward.

His team spends 80% of discovery calls listening and just 20% talking. They anchor every conversation in real pain points.

“No urgency? No deal. That’s the truth in today’s sales landscape.”

If a buyer says, “We don’t have budget,” Mike’s team brings it back to what they heard earlier:

“You told us you have 12 open maintenance roles. That’s budget. Let’s talk about how we can help.”

Sell top-down and bottom-up

You need both.

Top-down selling gets executive buy-in. Ask the big questions:

• What does your board care about?
• How are you measuring success?
• What’s the plan for the next 12 months?

Bottom-up selling uncovers insights from the front lines. Ask property teams:

• How’s foot traffic?
• What’s your tour-to-lease conversion rate?
• Why are renters walking away?

Connect those insights back to the C-suite. Build alignment across every level. That’s how you drive deals forward.

“The best salespeople don’t just sell. They teach customers how to buy.”

“Status quo is the enemy of action. If you don’t challenge it, you’ll never win.”

“Great salespeople think in terms of problem solving, not product pitching.”

Think big. Play to win.

Quota is the job. 200% of quota is the goal.

Mike helps his team dream bigger and execute smarter.

• Manifest big deals. Reps list their top five dream accounts every week and talk about them as if they’re already in the bag.
• Slow down to speed up. Bigger deals take time. Mike’s team takes extra steps to build relationships and bring in the right decision-makers.
• Seek feedback, act fast. It’s not enough to say you’re coachable—go after feedback, act on it, and get better every day.

“Don’t just play for quota—play to win.”

“Dream bigger, execute sharper, and think like a 1-percenter.”

“Manifesting big deals isn’t magic. It’s strategy, action, and belief.”

3 key takeaways for ‘Getting to Hell Yes!’

• ✅ Teach buyers how to buy Customers don’t always know the process. Help them navigate, map the journey, and guide them to a decision.
• ✅ Anchor every deal to the Cost of Inaction No COI? No deal. Find the pain, quantify it, and make it crystal clear why doing nothing isn’t an option.
• ✅ Think bigger than quota Quota is the floor, not the ceiling. Visualize success, aim high, and play to win.

Ready to get your customers to say “Hell Yes”?

Think bigger. Listen harder. Solve the real problems.

The market has changed—have you?

If you’re ready to learn more about sales leadership, selling in multifamily, or “getting to Hell Yes,” let’s connect. And if you found these insights helpful, share this with your team and start the conversation:

What’s holding you back from getting your own “Hell Yes” moment?

Let’s make it happen.