Hey, I’ve built a billion dollar company, I cashed out, and now I’m sitting on ten million dollars. Would you like to hire me for a 9-5. All I need is a 150K base salary. If you’re expecting someone to say that to you, you’re wildly out of touch with reality.

You’ve taken your company as far as you can. You have a few sales people, revenue feels stable, but you know you can impact the market in a big way. The only thing you’re missing is that right hand man who will come in and capitalize on the market potential. Now it can’t just be anybody, you want someone that’s already been there before. You want somebody that took an early stage company from 5 to 500 salespeople, multiple rounds of funding, and ultimately either an acquisition or an IPO. Now, your desires aren’t unwarranted, however, they are unrealistic. I want you to think this through logically, what is so special about your organization that somebody at that level would want to join you? Don’t tell me it’s your culture, don’t tell me it’s your solution, don’t tell me it’s the market. The truth is, nobody believes their kid is ugly. Everyone thinks their kid is the cutest kid in the world, as they should. But this person, as rare as they are, is not on the open market. If you truly had an organization that was worthy of a unicorn, you wouldn’t be looking for one. You would already have one. The truth is, you’re just like everyone else and you’re going to need to put in the hard work of developing your sales leader. First, you need to figure out what type of sales leader your organization needs. Second, you have to figure out what objective qualities this person will display if they’re the right person. And finally, you need a process to be able to attract and hire them.


Point 1

 What kind of leader do you need?

First let’s break down how you determine what type of sales leader you need. There is a difference between a wartime and a peacetime general. Is your organization at a point where it is stable, trending upwards, there is no market uncertainty, opportunities are plentiful, and you just need someone to maintain and steer the ship forward? If so, you need a peacetime sales leader. Now, if you have a market incumbent you’re looking to overtake or someone else is making serious noise and you need to destroy their momentum before it gets out of hand, what you need is a wartime sales leader. Another thing to consider, is this a person who is responsible for building the systems, processes, and onboarding sales people to ensure success? Because if so, you’re going to need someone who is operationally minded. However, if you’re still looking to find your differentiator and separate yourself from the market, you’re going to need somebody who can develop a creative strategy. Finally, what support are you giving this person? What are your expectations of what they will do? Are you looking for somebody to build a proper management structure with sales managers, sales operations, and all the other roles required to support salespeople? Or are you looking for somebody to simply help you take the next step by covering all the above in one role? Because that person will be more junior and scrappy vs. the individual, who is more senior, and will build the sales management from top down. This is the first thing you need to correct. If you don’t understand this, you will be barking up the wrong tree.

Point 2

Identifying the individual who fits the role.

Now assuming you’ve come to an understanding as to what type of sales leader you need, you need to be able to identify this individual. Again, there are many different types of sales leaders, and depending on your situation, their attributes will vary significantly. What I will say is, the type of sales leader that is needed in most organizations is a wartime sales leader who needs to be scrappy, and be held accountable for revenue and developing sales team culture. In order to identify this individual, you need to understand the characteristics they will portray. This person will not call themselves servant leader. They may come across slightly egotistical, but there is a difference between ego and confidence. Ego is someone who is looking for glory. Confidence is someone who is looking for a challenge. Is this person talking about what they can do or what they have done? I am always wary of people that talk about their past. I don’t care what you have done, I care about what you are going to do for me now. In the interview, are they telling you about how they would execute certain initiatives? If so, does it make sense? Do you like the idea? Does it feel aggressive and as if this person is putting their neck on the line by making bold claims? If so, there’s your wartime sales leader. Somebody who is egotistical and has no intention of delivering any results will talk a lot about what they’ve done in the past, will offer more questions than solutions and their go to line will be “well, we just have to test and see what the outcome is.” My friend, I’m not asking you to test, I’m asking you to execute with precision. Do you know what you’re supposed to do? Do you know what will bring me results? If so, great. If not, stop wasting my time.

Point 3

You want someone with a chip on their shoulder.

Now that you know who you’re looking for and what they look like, you just gotta find them. One place they most certainly are not, is on the open market. This person is not unemployed. This person is gainfully employed, making a serious amount of money, but is restricted with what they can do based on their current leadership structure. I would work with a sales recruiter and focus on organizations that have recently passed on promoting a sales leader from within, and brought in someone from the outside. In there, you may find your diamond in the rough. Now understand, these are people that have been passed up for promotion. This likely means they are not ready to lead at that level. However, many organizations pass up the right person, just to bring in someone from the outside. So while most that have been passed up rightfully so, there is a person on that list that should not have been, and is pissed off they were passed up. This is the person that will come in with a chip on their shoulder, looking for a new challenge, looking to prove what they can do. That is the person I would put my money on.

Conclusion

So while you feel an ideal situation would be a unicorn walking in the door, and taking your business to the next level. The reality is this, in order to get there you need your wartime general. Your diamond in the rough. This person may be a little harder to find, but will pay off in the end. Your effort on the front end will dictate your success for the long term. Hiring the right sales leader is tricky when you don’t know what it is you’re looking for. Sit down, be disciplined, understand it will not be an easy process. But when you find the right person, you will understand why you waited so long.

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