The Cheap and Cheerful way to find a Great Sales Leader

Don Rainey
Landing on your feet
6 min readJun 25, 2020

Finding a strong leader for a sales effort is one of the hardest things to do. There’s adverse selection in the candidate pool and endless competition for suitable candidates. Most of the candidate pool is people who failed in their previous position. Poor candidates are usually not employed for good reasons. You’ll find them quickly when you start looking. Ignore them. The reliable producers are highly compensated and often in secure jobs. That doesn’t always mean they’re happy there. It certainly doesn’t mean they can’t be more pleased with your organization.

Photo by Austin Distel on Unsplash

Regardless of satisfaction, most successful individuals have invested themselves in their position. It would be best if you enticed them to walk away from reaping rewards of their previous hard work. A strong candidate has to factor the value and effort of starting over with you vs. the expected rewards of their current position. The better they are at their work, the harder it will be for you to entice them away, unless you highlight the opportunity to assess the potential upside for switching teams.

It isn’t solely about the money. Strong sales leaders will need more than income to make a switch. Remember — they are already succeeding and making a good income. You have to get them to see how succeeding with YOUR company is in their best interest — not just yours.

The two-step process to identify and recruit a successful sales leader will take some leg work. First, you have to find them. Then establish bona fides (remembering they’re good at selling, especially themselves), and finally, you have to convince them to leave their secure position. This article will cover how to identify a suitable target and some tips for recruiting successful sales leaders away from a stable job.

Identify the Target

A great sales leader has 1. A track record (duh), 2. a defined sales process, and 3. devoted salespeople. The target’s track record must be verified with independent sources, ideally previous CFO’s. When you are checking out a candidate’s track record, ask for names of other sales leaders the contact has worked with to compare your target to. (This can potentially give you a future target.)

I can’t understate the value of a well-defined sales process. Every successful sales leader has one. The process should include recruiting and training salespeople as well as prospecting, qualifying, and managing predictable production. A strong sales leader will always have a repeatable process. Always. While the specific details of a sales process the target uses is a topic for the interview discussion,( as you will learn a lot from discussing it), the absence of a process is a nonstarter if the target cannot or does not describe a process, pass on them.

The presence of devoted salespeople means there are successful team members who will readily follow the leader into a new company. Of the three identity characteristics, this is the most valuable and reliable reflection of a sales leader. Check if your target has ever successfully recruited team members from previous positions. People won’t follow a weak leader, bad manager, or an ineffective executive.

Strong salespeople, like their leaders, can be tough to find. Finding a leader with followers is doubly beneficial. It confirms the skills of the Target, and it may also be a source of salespeople for the team.

Once you have identified targets, you need to dig a little deeper. You can’t call the current employers of your targets. But you can reach out to their previous employers. Reach out to your target’s former salespeople, which are easier to find and less disruptive. LinkedIn can be a great way to find these connections. Search the applicable companies and correlate timelines. When you reach out to a link of your target, don’t seek a personnel reference. For discretion purposes, you do not want to expose your target, so instead declare an admiration for the company’s sales process, for example, and ask your contact about it. Everyone has an opinion of current and former managers — and they will usually offer it on your target. How a salesperson describes their experience with your target will enable you to determine if you should take the next step.

Recruit the Target

Identifying sales leader targets is much harder than reaching them. It is easy to reach them. Sales professionals are in the business of being accessible. You can reach out to them for a call or request a casual meeting about their sales process (which you’ve researched, after all). State your desire to tap their expertise and seek insights. Pride of authorship and ownership of a successful effort is human nature. They’ll be inclined to share it with you — which means they will talk or meet with you. Now you can start recruiting.

It is a valuable stage of the recruitment process, whether or not your target is advanced to the next step of recruitment. You will receive incidental data on compensation plans and quotas when you speak with your target — which is a valuable byproduct of these conversations. Additionally, since successful sales leaders maintain a network of people who adhere to the same processes and principles, your initial target might make useful referrals of salespeople or peers. Ideally, they self identify as a candidate during this conversation.

To recruit effectively, pitch your opportunity first and close with compensation. People leave jobs because they don’t like their boss, don’t see opportunities for growth, or seek higher pay. In that order. Be prepared to share your vision, its’ importance, and tout the working environment. Sell the opportunity for growth. Yes, the compensation is key, which will create your new highest-paid employee (sorry, their package will be more than yours), but it won’t generate desire in the target.

The opportunity you are presenting — with the company and for the prospective hire — have to be at the forefront of the discussion. You must differentiate how and why your company is a better, more fulfilling, more pleasant place to apply their skills.

One of the compelling offers you can make to a desirable sales leader is sitting at the decision table — the table where decisions are made by management influencing the target’s success in your company. Discussion of product, pricing, marketing, support, and service are examples. All too often, sales input in these areas, is undervalued or ignored. If you can genuinely offer a role in which your sales leader is involved in executive decisions, you may be offering a truly compelling position.

You might note that I haven’t mentioned hiring a professional recruiter for this process. That’s deliberate. They’re expensive, and good ones are rarer than good sales leaders. The headhunter industry’s typical guarantee of finding another candidate if the first fails is small compensation. Consider telling them that you only want to recruit currently employed candidates to avoid adverse selection. I’m not saying they’ll like this (it is a lot more work to find those candidates), but their response to the request will be enlightening. Require interviews with former salespeople, especially ones fired by the sales leader. If you can afford a recruiter, make sure they follow this process on your behalf. If you do, you’ll get your money’s worth.

Initially, most small company sales efforts are by the CEO. Supplementing yourself with a substantial addition will free you to do more for the company. It is worth the effort and the money to make this move to enhance yourself. Find and recruit a strong sales leader. Look for these key attributes to identify your Targets, avoid negative selection bias in the candidate pool by avoiding unemployed or “between opportunities” sales professionals, and pitch the position on more than money.

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Don Rainey
Landing on your feet

Veteran venture capitalist and father of six. Love life and the startup experience. I write to pass along what I’ve learned.