“Step Out of Your Own Silo:” Ryan Lahey’s Approach to Sales

When Ryan Lahey thinks back to the jobs he worked as a kid, he says, “There’s definitely a flavor of sales, in all of them.” At twelve, he was a caddy. Then, he sold newspapers outside of a breakfast shop. He sold shoes. Ryan’s dad was also a salesman. He owned a gutter company when Ryan was young. “As I got older, my dad worked for Pella Windows, a big national window reseller, and that’s what brought us to Massachusetts. And then he started his own company about 15 years ago, where he sells custom windows and doors in the Cape and Islands area.”

Ryan stayed in Massachusetts. Black Kite, the cyber-risk platform company he works for, is located in Boston. He lives nearby. But his Bruins paraphernalia is tucked just out of shot on Zoom; New York is his territory, and he has a Rangers flag right behind his chair. (It’s not really insincere; his family roots for the Rangers.) “So, it’s a talking piece. Everybody asks about it.”

DISRUPTING THE GRID

Ryan’s more obvious foray into the world of sales came after college, when he got a job as a door-to-door salesman. “We were basically a little shop that would get hired by some Fortune 500 companies to do door-to-door marketing and advertising.” The company Ryan’s employers were supporting when he started was an energy company trying to break into the North Boston area. So Ryan would approach prospective customers and say, “Hey, we can keep your rate flat throughout the year.”

Door-to-door wasn’t Ryan’s favorite thing to do in the world—“I actually hated it”—but there were nuggets that he did like: being creative, conversing with new people, and helping them solve problems.

This makes sense, given the way he thinks about his profession. To Ryan’s mind, the number-one characteristic of a true salesperson is intellectual curiosity. This, he says, is something he learned about when working with Maestro in the context of learning how to ask the right questions at the right time. “But also, just generally being curious about the way [prospects] do things, why they’re doing it that way, and what they’re trying to accomplish as they look at a new solution or a new company like mine to work with.”

The other two top traits for Ryan are grit and competitiveness. “It’s not necessarily competing against your own team, because I think there’s enough of an addressable market within every industry that everybody on your team could hit their numbers easily. I think it’s more so a competitive desire to be a better version of yourself every day, to continue to learn, as a sales professional.”

As is the case with many of the salespeople we’ve spoken to, Ryan has a history of competing in sports. In high school, he played hockey, golf, and tennis. It’s not just the competitiveness he took away from the experience, though. “I think in sales, it’s such a team sport.” He thinks a lot about the dangers of residing in a “silo” as opposed to operating together with other professionals. A supportive infrastructure is one of the things Ryan likes most about Black Kite, where he is currently an account executive. “You have that executive level of support, and you have access to training, to tools, to all these different things.”

NOT THE 80-YARD LINE

What surprised Ryan most about sales were the almosts. “Just as you think you’re like, ‘Hey, I got this, everything’s going incredibly well,’ then you may hit a valley, and that goes back to the importance of continuing to learn, leveraging your peers in the industry, hopefully having a mentor that you can bounce things off outside of your own leadership. So, I think that’s part of also taking a step out of your own silo and talking to somebody in a different industry, or that targets different companies.”

One of the things Ryan learned from Maestro during his training with them in 2021 was that a prospect saying yes is not the finish line. Not even close. “It’s almost like the 50-yard line. People think it’s the 80-yard line. You’re in the red zone,; they tell you they’re ready to move forward. No. Procurement, legal, sourcing. All of that is maybe the most strenuous and difficult to manage, especially because so much of it is out of our control.”

And the funnel has stretched out considerably since Ryan started, with the number of decision-makers increasing. “I think the stat is like 10 to 12…I think that can honestly double at some of these Fortune 500, maybe Fortune 200, companies.”

It’s hard. “What’s that saying? If you love what you do, you don’t work a day in your life? I love sales, but I’m definitely working a day in my life.” This is one reason the wins mean so much. When Ryan thinks about his best sales experience to date, he zeros in on a recent food-and beverage-industry sale. “It was a 60-day process where we ran these very tailored specific workshops throughout the duration of that engagement. And basically, we would parachute in our executives to host these workshops to walk them through… And we really segmented off the parts of the platform that applied directly to their use case and to the outcomes they were looking for.” The result? The client said it was the best buying experience they’d ever had.

This is the type of experience that makes the hard work worthwhile for Ryan. So, did he see his profession coming a mile away? We asked if he’d always known what he was going to be. According to Ryan—former caddy, former newspaper salesman, former shoe salesman—if he didn’t realize he was going into sales, he should have.

Ryan is currently an Enterprise Account Executive at Black Kite, a cyber risk-detection-and-response platform. You can learn more about Ryan here. Be sure to congratulate her while you’re there!