So, You Want to Make a Midcareer Shift Into Sales

We have a lot of conversations about starting out in sales. The implication in many of these conversations is that we’re talking about young people launching their first careers. But they are not the only cohort entering the sales world. For some folks, job changes are so frequent, they’re basically the norm. Take, for example, this particular economic news release from the US Bureau of Labor Statistics, which focuses on elder millennials (try saying those words to my face). It looks at the average number of jobs that 18 to 36-year-olds worked between 1998 and 2021. Nine. Nine jobs on average.

The BSL clarifies that it does not report on number of career changes, because it’s tough to actually define what a career change is. That’s a separate conversation. But I think it’s fair to say that we should be including people of all ages in conversations about those who are new to the sales field.

Go online, and you’ll find differing opinions on whether and how to make sales your second career. I got front-row seats to a particular perspective; I went to Adam Rosa, who, in addition to being part of Maestro’s own training team, does recruiting for our clients to great success.

THE NORM

Anecdotally, Adam doesn’t see a ton of people getting into sales as a second career, “but they tend to be be the people who stand out more.” Why? “Because they tend to know what they want. They tend to be hungrier. They tend to feel like they have to prove themselves.” As you might have suspected, that can be a great thing in sales.

YOU SHOULDN’T, BUT THERE’S A GOOD CHANCE YOU WILL…

Unfortunately, it wouldn’t be surprising if you were to encounter biases upon trying to enter the field as someone who has been in the workforce for some time. “Ageism is a thing,” says Adam. “It’s illegal, but it’s a thing. People will look at you and go, ‘Oh, if I’m going to go with someone who’s new, I’ll find someone who’s young.’ They are wrong for doing it, but that doesn’t stop it from happening. Knowing how to get in front of it is vital to breaking their bias.”

Adam says that part of hirers’ skepticism stems less from a distaste for someone’s age than from a different question: “why didn’t you do this earlier?” People may wonder about what you were doing before making this decision—and why you chose to stop doing it.  A less close-minded way of asking this question is, “why now?” It would behoove you to be prepared to answer one or both of these questions, which may be asked explicitly or implicitly.

Personally, Adam is “content with people just giving the honest reason, whatever it is. So I think sincerity is the best answer to that…And the reason why I say sincerity is if someone says to me, ‘because I realize I can make more money,’ awesome. I love that. I can motivate people with money—easy. If they say, ‘because I realize it’s challenging, and I am feeling bored, and sales is a challenge,’ that’s great.” What he likes to see projected is drive.

THE ANSWER INSIDE YOUR ANSWER

Regardless of what specific circumstances brought a candidate to sales, there are certain things Adam is looking for in the way that candidate answers this question. “Is your response indicative of the fact that you will remain in this field, and you’re not testing the waters?”

When talking to a candidate, he wants to know that they know, are certain of the fact that, they want this. This, by the way, also ties back to another concern that can breed ageism in hirers: career longevity. The same way they want to know that this profession is not just a passing interest of yours that you may abandon after a year or two, they may also (whether they say so or not) wonder if you plan to retire in the near future. If you know you are nowhere near retirement and see yourself in this field for many years, you can be explicit about this. The later in your career you decide to enter sales, “the more you have to really be able to answer the why and show me that you’re still hungry.”

YOUR SALES BACKGROUND

“If you had any sort of experience in sales, even if it’s retail, even if it was a sandwich shop…having some sort of anecdote of ‘I’m familiar with the sales world’” is relevant.

Remember that you are not just talking about what you have done and experienced, but how you are able to understand and use that experience toward success in a sales position. “You have to show the experience you have and how that’s going to relate and give you a leg up.”

YOUR TRAITS AND SKILLS

For Adam, it often boils down to these two words: traits and skills. “Are they competitive? Are they self-motivated? Are they organized?” It can be useful to draw on your accomplishments and experiences in whatever field you’re coming from to illustrate “ways that you’ve pushed yourself in other roles—things that are tangible.”

Another thing he looks for? People skills. “One of my favorite things to look for when searching for a BDR is, ‘Hey, were you ever a bartender, or were you ever a waiter or waitress?’ These are really exciting for me, because they show that you have people skills. Tangible skills.”

An additional way to demonstrate that you are serious about taking on a career in sales is showing that you have already invested time and effort into it. “Have you done sales training on your own? If you’re coming into sales late and you haven’t told me that you’ve looked up the Maestro DRIVE training, the Challenger Method, Sandler training, if you haven’t done research on your own, I’m almost always going to disqualify you. Because it shows me that you’re testing the waters, and I don’t want someone to test the waters. I want someone who’s going to put in effort into a career and go, ‘Yeah, no, I looked all this up. I did all this training. I’m ready.’ Because it’s the investment. Are you making an investment into yourself? If you can’t make an investment into yourself, I won’t make an investment into you [for] the company I’m supporting.”

YOUR SENSE OF DIRECTION

Here’s another bias latecomers to the industry can face: according to Adam, people may see them as “without direction, without maybe a vision. That bias is wrong. You can be very motivated and recognize that there are better opportunities as you’re open to more experiences…That is a very common bias, and I think that that’s wrong. I think people who move into sales later can be great. You just have to know what to look for.” But not everyone is like Adam. If this line of thought is one shared by various people in hiring positions, it behooves you to be aware of that bias.

WHAT’S NEXT… OR FIRST?

• As Adam says, it can never hurt to take steps that show you are serious about your prospective sales career. This can mean getting certified via various programs and trainings (though be wary of dropping money before you’ve done your research into which ones are considered valuable and respectable).
• Get acquainted with the ins and outs of the sales profession—“learn the industry,” says Adam. He recommends leaning on a mentor, if you can find one, to identify what you should be learning. You’d be surprised how many of the sales world’s leaders are willing to share advice if you reach out earnestly, even if they don’t have time for a full mentoring relationship.
• Understand that sales is not always lucrative—but it can be—but it isn’t always out of the gate.  “I think sometimes people who are hopping in are like, ‘I want to go make a hundred K,’ and I’m like, ‘You’re not gonna do that, because you don’t have any experience and you’re not qualified. But the first year, you can go do really well, and then and then win a significant pay raise in your second year.” Long-term planning can help with this, says Adam.

SO, SHOULD YOU?

We’re not presumptuous enough to answer that one on your behalf. But here are some words of wisdom as you litmus test yourself. “If you’re someone who doesn’t mind failure, I would say I think sales is an awesome career for people who can continue to go after a no. I think if you’re someone who is looking for something that is secure, and that you won’t fail at, sales is not for you.”

It’s a hustle, to be sure, and it’s often a really hard one. It has no guarantees. Just know that, if you choose to take it on, we’ll be rooting for you!

Accelerate your sales with DRIVE! Maestro’s information-gathering lessons are available online for FREE. Go to this link and click the “Enroll Free” button.