The Pro: Mark Kosoglow
Title: Head of North American Sales
Company: Outreach

Various Age Groups Have Different Motivations
“In the same way that we segment companies out by size, employee happiness needs to be similarly assessed. Millennials want to be valued. They want to know that their company is investing in them, and they want to see a path to advancement that’s like a video game with different levels, so they know if they keep doing what they’re doing, they’ll advance to the next level. Meanwhile, veteran employees want influence and to be heard, and they want to know companies won’t get in their way. Money isn’t always the answer.”

Know What Makes Individuals Tick
“Company leadership still treats everyone the same. They don’t take the individual’s needs into consideration. The days of Mad Men are over, when employees’ personal lives were a secret. Sometimes sales managers are too busy being professional that they’re not personal enough. And then they tend to look at hiring as a plug-and-play process and just try to fill the positions. But then managers start to say, ‘Well, if we have to go through four people to fill this position, then we’ll go through four people.’ And they will!”

Retention Isn’t Always About Compensation
“Money is a big reason sales reps decide to stay or leave, but the key factor is if they’re being challenged. A rep might even make good money but move on because they’re not being challenged. That was my experience; I was on cruise control and I wasn’t engaged. I think even with my pay staying the same, just having another responsibility or two would’ve convinced me to stay. It doesn’t always have to be a promotion – just expand reps’ responsibilities. Recognize sales reps for their great performance and ask them to build a training curriculum for other employees to help them perform just as well.”

Watch for Warning Signs
“I think the majority of the time management knows when a rep is going to leave. Occasionally, it comes out of nowhere. But usually, when they think about it more, they realize they had been hoping there wasn’t actually an issue. Managers need to have difficult conversations with their reps if they’re seeing warning signs, but they hesitate because it’s awkward and uncomfortable. We’re not trained to have those conversations, so we just avoid them. But these talks are a way to really get to know someone and that’s why I now love having them.”

Make Sure Reps Are Heard
“If reps know they’re genuinely valued, that’s a huge hook. They want to feel they’re contributing. Does the manager have a personal relationship with the reps? Because then the manager and the sales team can have difficult conversations and hold them accountable. Keeping and retaining talent is a company’s biggest competitive edge. But there’s often a take-it-or-leave-it attitude among managers toward their reps, and those companies will always be behind the firms looking to get better. Management has to be focused on retention, which makes them more intentional, and in turn more successful. It doesn’t just happen.”

Mark Kosoglow is the Head of North American Sales at sales engagement platform Outreach, where he’s responsible for building the sales team. Mark joined Outreach in 2014 as a 100%-commissioned contractor, with a personal mission of helping more sales professionals win. He is also co-author of The New Rules of Sales Engagement.