When it comes to your sales career, it’s important to always keep your options open without being reckless. At one point, I actually had eight sales jobs over the course of 12 years. Some would see this as a hit to my resume and take a negative view of it. “What’s wrong with her?” “Why is she always switching jobs?” “Is she unreliable?” But for me, these moves ultimately made the difference in growing my career, my network, and my personal development.
Throughout all of these experiences, I learned a thing or two about when it’s time to move to your next sales job.
I’m a firm believer in always giving your existing employer a chance to keep you, especially if you really like working there. I switched jobs often because I knew I wanted to challenge myself with more accounts, more people to manage, and more responsibility. If I didn’t see these opportunities available to me, and I had a proven track record, then I always took the opportunity to speak to my manager. I’d say, “I feel like I want to challenge myself more. I love working here, but how can we build a plan to help advance my career and increase my responsibilities?”
I often swung for the fences in my requests. You know the saying, “Never walk in with a problem without a solution.” Don't bring up career moves without an idea of what you might want to do. It might not end up that way right out of the gate, but at least your employer knows you have given it some thought and it's not an emotionally charged “I want more” request. At one point, I wanted to go from managing no one to a team of 50. I realized I might not be ready to manage that many people people at that point in time, but that maybe I could take on a team or two. And after I proved myself, perhaps I could take on a little more responsibility.
However, there was always a method to my process. After I asked for new opportunities, I typically gave 60–90 days for my boss to come back with something that might work. Seven of the eight employers I had said, “We really value you, but we don’t have anything for you right now. We still want you to stay, and hope you know if something opens up which we feel would be a fit, we will let you know right away.” At that point in my career, I felt I had nothing to lose. I was confident in my capabilities, I just needed the opportunity to challenge myself in new ways. Because of this, I would make the difficult decision to move on.
It isn’t just the sales managers who need to take responsibility in keeping you engaged and employed. The company must also have a philosophy of how to keep and develop strong talent. Otherwise, you have no choice but to take the leap to a new place. Think about it this way: Sales managers should be cultivating leaders, and identifying and cultivating their own replacement so they can move up as well. Are they investing in you and your potential career opportunities? Do you feel like you have the freedom to apply to different roles in the company if an opportunity presents itself?
Managers must be committed to you and your career — this is the key to retention. Having been a manager myself, I know not everyone is created equal and I had to manage, mentor, and coach people based on what was right for them, even it it meant developing them to ultimately move on to another role or company. But the bottom line is your boss should run through fire for you and be a supporter of your career, not just the job you are doing today. If that is not the case, it may be another sign it’s time to move on.
Going back to how you should first try to stay, I’ve had managers tell me they couldn’t get me what I wanted but that we should “get creative.” I really appreciated that and the value they placed on keeping me. But I also had to make a decision about whether this was best for me in the long run. And it wasn't always easy. My emotional decision would be, “Oh, they've done great things for me. I should stay." My professional mind told me, "You've got to go.”
It’s always important that you give the process a chance. For me, there weren’t acrimonious splits or just deserting a team or a company. I never wanted any of my former employers to say in the future, “Well, she just bailed on this job and went to another one. It seems that’s what she is like.” Instead, I wanted them to say, “It was really tough losing her. We tried to keep her, but we just couldn’t.”
You need to look out for yourself and your career growth. Follow what is right for you. A sales career is a long game, a marathon and not a sprint, and you must maintain a good reputation. We might think that the sales industry is large, but the truth is there is the reality of “six degrees of separation.” How often do you meet someone and they say, “Oh, I used to work there. Do you know this person?” It happens so often. You never want to burn bridges along the way, since you never know when you may need to lean on your network.
Change can be hard. Heading out to an entirely new organization and team will take some work, so you need to be prepared once you make that leap. In your first 90 days, take an inventory of where you were at your last job, and what you want to accomplish in this new role. This is an entirely clean slate for you; take advantage of it to map your career destiny and your future professional self.
I often say that sales is a team sport. Take the time in your first 90 days to get to know not just your own group, but other departments, from product teams and customer service, to billing, logistics, and marketing. For example, you want to have that friendly relationship with finance when you have a last-minute deal needing a quick turnaround on pricing approval. Sales isn’t just external — it’s internal, too.
And, finally, you’ve hopefully built great relationships with clients at former jobs. Treat them with respect, and don’t make the assumption that their business will follow you to your new role. Don’t abuse or lose the trust you have spent so much time creating and nurturing. As a trusted advisor, leverage those relationships thoughtfully. Use your relationships wisely, as they will ultimately support you as you move throughout your sales career and onto the next opportunity.
“Don’t abuse or lose the trust you have spent so much time creating and nurturing.”