How Kyle Healy Sells: It Comes Down to Treating People Like People

Here’s a first: Kyle Healy got into sales because of longtime New York Knicks play-by-play announcer Mike Breen.

Kyle went to Ithaca College to become a sports broadcaster. After graduating, he managed to land a job for the MSG Network, working in Midtown Manhattan’s historic Madison Square Garden.

There, Kyle met one of his heroes – Breen. Given this golden opportunity, Kyle asked the broadcasting legend what his advice was for breaking into the business.

Breen’s answer – think twice about doing so.

“He was a great guy, although he was honest with me,” Kyle said. “He said it’s a tough, long road, and very few people make it. And even if you do make it, it means working on weekends, working on holidays, traveling always.”

Kyle couldn’t ignore the advice. So, he went home, where his dad had his own insurance brokerage. Kyle started selling for him, and he proved to be good at it.

Success has followed. Today, Kyle is the Vice President of Sales Enablement at NFP, one of the world’s seventh-largest benefits brokers by global revenue.

What has Kyle learned as he’s climbed up the ranks in sales? How is he coaching his team to sell in this confounding time? What’s a habit he has outside of work that helps him perform better at work?

We asked him all of that and more in our latest edition of How I Sell:

1. What motivates you each day, even when you aren't feeling it?

I think it's ego. I'm a people pleaser, so I want everyone to be proud of me and to think I work hard, right?

I don't want anybody to be disappointed in me, whether it's my boss, son, or colleagues.

So a lot of it is wanting to set a good example, but I think it's a little ego. I don’t want to fail, I don’t want anybody else to think I failed, I don’t want to mess up, I want to do my best for as long as I can and make everybody close to me proud. So a little pride-driven too.

2. What's your sales philosophy, in 3 sentences or less??

Do the right thing. Put your customer first.?

I know it’s not revolutionary and I’m not the first person to say it, but that’s just always how I’ve done it. Do the right thing and put your buyer first.

A quick story. When I was first starting out with my dad, for renewals, he would not propose the most expensive plan. Of course, when you sell insurance, you get paid commission. So the bigger the plan, the bigger the commission.

I was very confused. So I asked him why he wouldn’t propose the most expensive plan.

He told me that he proposed what was best for the customer and their budget. Even if you were able to convince the customer to buy the more expensive plan, someone's going to come in behind you and show them the right one. And so you're going to make more money but only for a short period of time, versus a good amount of money over a very long period of time.?

He told me, it’s not about how much money you can make right now, you are 22 years old. You want these people to be your clients for the next 40-50 years, so don’t screw it up and build a good book of business.

Eventually, we sold our brokerage to NFP, and they interviewed me to sell for them. The interview was probably 15 minutes, and the managing partner for NFP told me that if you’re going to be successful here, our clients always need to come first and we always do the right thing.

And I was like, “Well, that's what my dad told me too. I respect him quite a bit. And so if that's how you run your business, I guess I can work here too.”

That's where it comes from and it hasn't failed me yet. Just do the right thing and put your buyer first.

3. In today's noisy times, how are you encouraging your sales team to make their prospecting stand out?

We focus a lot on research and understanding.

I use a sports analogy. Once you reach out, what we like to say is that's the game. That's under the lights, you're in the arena now.

But, if you study the best athletes, what you find is that they spend 90% of their time on preparation, and 10% of their time actually playing in games.

And so that's what we try to instill in our salespeople, right? We want our reps, before they reach out to someone, to feel like they really understand who that person is, the role they have, and the company they work for.

We do B2B sales. So we try to help our sellers understand how people buy and why people buy. And, oftentimes in a B2B motion, it's not even about the person. The person takes on the personality of the organization, so it’s understanding the personification of organization-buying behaviors.

We want to come at them right off-the-bat, having them feel like, “Wow, it’s like we’ve already spoken.”

To make this programmatic, we've invested in a buyer research division. So we put programmatic qualitative and quantitative research-based studies out to the field on an ongoing basis across a number of different topics.

Because if we want to be buyer-centric, we need to understand our buyers. And if we're really gonna understand our buyer, we need to do this scientifically. We need to do it programmatically. We need to be disciplined about it. There needs to be a trend to it. We need to run the same programs year after year so we can see how buyer behavior and decision-making has changed. And that research has to be delivered to the field in a way so that a seller can absorb it and adapt to it quickly.

So yeah, that's how we do it.

4. Buying committees are getting larger — and more cautious. What's the key to overcoming that?

We’ve always said, as buying groups get bigger, our selling groups get larger as well.

That’s because the problems are becoming more and more complex. By the time the customer decides they’ve got a big enough problem to fix, we need to bring multiple recommendations and solutions to them. And a rep can’t do that all on their own.

So, sales becomes more of a leadership position, where the rep is bringing in the right people at the right time and matching needs with expertise.

Also, there’s a couple of different ways we think about more effectively engaging with larger buying groups.

One is starting early. We know the roles and personas that are often involved in the buying process. Even if you, as a seller, don't have any engagement with them at first, you need to know them, right?

So we won't let our sellers qualify an opportunity and move it into full pipe unless they can tick off the people that fit all of these roles.

We know all of those people are going to be involved in the buying decision, so at a very early level at least our reps have identified them. Then, there needs to be some form of engaging with them. Even if you aren’t meeting with everyone face-to-face, our reps need to ensure that the first time the members of the buying committee see their name isn’t in the final decision.

So, send those who you haven’t engaged with something of value. Maybe an article or research that would be interesting to someone with their position. Something, so they at least know who you are.

And then when you get to the final decision, it’s ensuring everybody is in the room. Make sure you are asking the right questions along the way so everyone who needs to weigh in on it is in that meeting.?

Otherwise, if you don’t, then you are relying on your champion to make that final pitch for you to someone who might’ve never heard of you.

5. What's the best piece of sales advice you've ever received?

One of my original sales managers said, “Treat people like people.” Which seems so simple, but when you start treating your buyers like targets or numbers as part of quota, you miss what’s inherently good about sales, right? Which is aligning whatever product or solution you have to a problem someone else has.

Ultimately, you're connecting your buyer to a solution that they maybe didn't even know existed and fixing a problem for them. There's a warm, fuzzy feeling that comes when that happens.

When you start to debase the profession by seeing people as numbers and “big game hunting,” you miss all the warmth and fuzziness that comes from realizing that you helped someone and made a difference.?

If you put the buyer at the root of it all and treat people like people, you'll be alright. It'll all work out for you in sales.

6. What Sales Navigator feature do you find to be the most useful?

The new Buyer Intent features are very helpful. I love being able to see which companies are interested in our company.

We're doing a lot more targeted advertising on LinkedIn. And then seeing different people and companies engaging with that advertising through their Buyer Intent Score, which is very helpful.

So I think Buyer Intent has been game-changing.

I also like the Book of Business feature, where you can upload your book and then keep track of your key leads and accounts. Especially the last few years, with the Great Reshuffle, that feature was game-changing because people were moving at such a high volume it was impossible to keep track of them without that.

Honestly, there's so many good features. We use Smart Links a ton. But Buyer Intent has been top-of-mind recently, as it’s been helping us prioritize who to focus on.?

7. Is there any habit you have outside of work that you believe helps you perform better?

Resistance training and fitness competitions.

I was diagnosed with Stage 3 cancer six years ago. I went through chemo radiation and fortunately survived it.

But how I sold prior to that and how I sell now is light-years different.?

Before that, I was out five times a week gladhanding and doing dinners, all sorts of stuff, and not treating myself well. Now, I’m really into putting the right stuff in my body, taking the right supplements, taking care of myself first, and making sure I’m not overworking.

And that also means getting in an exercise every day, no matter what.?

Really, it’s been game-changing in terms of my ability to focus, my cognitive function, my energy throughout the day, on and on. I’m not getting those 2 p.m. crashes anymore where I need to chug Starbucks to make it through the day.

Also, any kind of regular health pursuit builds discipline. And that correlates really well with being successful in sales.

8. What has been your biggest failure in sales and how did that experience transform you?

There are two.

When I was 26, I fell flat on my face over-promising to a large customer. I wasn’t focused on my buyer, I didn’t care what they were saying to me, I just wanted to sell to them because they were big and I had a shot.

And it was super embarrassing, I did everything wrong.

I got into the finalist meeting and I had my boss with me, who I had convinced we had a good shot when we didn't. We were sitting in a room with the CEO of a 5000-person company and the CEO undressed me pretty good.

I was completely unprepared. Nothing we were talking about aligned with what they were looking for.?

But I had come to the point where I thought I could tap dance around anything, right? Because I had been pretty successful for two years and so I thought it doesn't matter what they think they want, I'm going to convince them that they want me.?

And that was pretty humiliating because that was supposed to be an hour-long meeting and it lasted 15 minutes. The CEO of that company asked me and my boss and our whole team to leave and it was all my fault.

So that was crushing.

And then, in my current role in sales leadership, I have learned that much like in sales, the buyer needs to be at the center of everything we do. And, in this case, my buyers are now my salespeople.

When I started, I tried to assemble early on what I thought would make all of our salespeople better. But I wasn't listening to our salespeople enough. And I was trying to make them things they weren't.

I just felt like I had done the research, I had done the due diligence. I know what's best. Just do it my way.

And not everybody needs to do it my way, right?

Just like I don't know what's good for every buyer, I need to listen to my sellers and hear what their biggest problems are before I recommend a solution for them, right? I found myself doing the exact opposite with my salespeople and that was hard, too, taking some harsh feedback. And not having us grow the way I thought we would.

Stepping back, I realized I didn’t listen to my salespeople enough.?I didn't identify the points of friction in their motion that I could help them eliminate. I just tried to give them a whole bunch of cool stuff thinking that would immediately make them sell more.

So I'll say those both were learning moments. It goes back to the beginning of this conversation — I didn't spend enough time listening. I didn't put the buyer or the ultimate customer first. I thought I knew best.

I got too cocky and went in and learned a tough lesson.?

Unfortunately, I had to learn it twice in two different roles. Bottom line, if you put your customer first and do the right thing, things tend to work out. And in those instances I didn’t.

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