Joseph Monahan on Developing Sales Talent

Joseph Monahan runs sales at Ylopo, a 200 person company that helps real estate agents and teams scale their lead gen through AI voice calling + text outreach. Before that, he ran a build-your-sales-team-from-scratch agency where he built over 10 killer sales orgs that have closed 10s of millions of dollars.

Joseph sat down with Luke to discuss building authentic rapport, the human side of sales leadership, and why the best coaches aren't help desks.

On building genuine rapport in emotional sales

The space I operate in has a lot of B2C aspects to it. Every single person we sell to pays directly out of their pocket—it's their debit card from their kitchen table office. When someone's business expenses come straight from their personal finances, the decision-making becomes deeply emotional.

So confirming they're on the right path and showing them they're not alone makes a huge difference. It's not always an ROI-based decision. So when you get them to feel how we will improve their day to day, it influences buying behavior in a meaningful way.

On systematizing authenticity across teams

After three months, most of my reps have examples for 90% of the scenarios they'll encounter.

I tell them to hold onto specific customer stories—remember this one because you're going to see it again. When you help people build these references, they can naturally relate to prospects without sounding scripted.

The key is reminding reps they've helped people in the same situation.

On proactive coaching vs. playing help desk

Too many leaders operate like a help desk—"I'm here when you need me." But if your reps are struggling, they won't tell you until it's the end of the quarter and you're looking at failed numbers.

It's like parenting. If your kids are doing shady stuff, they're not going to tell you about it. You have to keep your eyes and ears open.

So I spend time listening to calls and joining demos with my team. Most of my AEs are surprised I like to join—"This hasn't happened before." But we should be the experts bringing them insights, not waiting for them to ask.

On focusing your coaching efforts

I used to jump around KPIs too much—talk time's low one week, pricing issues the next. I'd have ten different coaching points in a month.

Now I pick three North Stars for the quarter and hit them repetitively.

On hiring for team balance

It's good to have all personality types on your team. If everyone's the same, nobody learns from anybody.

I want one high-activity person, one who's more process-oriented, maybe one who's loose around the edges. When people see someone being successful doing it differently, they're naturally pulled to try that approach.