A Selling CEO

One of the most valuable species of CEO is that they are “a selling CEO.”  The coveted selling CEO. Pretty much every early-stage company possesses a selling CEO. 

There are a lot of reasons for this but we see three main demands of a selling CEO:

  1. CEO must identify product: market fit
  2. Gain first-hand feedback from potential customers
  3. Begin to formulate the dynamics of the sales cycle

Ultimately a business must generate revenue traction, even if in a small way,  in order to prove its viability and potential sustainability.  And besides, most of the time, there is no one else to perform these tasks but the CEO.

Sooner or later though, if the business takes root the CEO must crystallize the sales function. And that is generally one of the most difficult tasks for any CEO, newbie or experienced.

Interviewing Salespeople: Reduce the risk

You’ll consider a lot of factors when interviewing salespeople:

  • Is the candidate a hunter or a catcher?
  • What compensation will most effectively motivate that salesperson that will fit in the budget?
  • Will they respond positively to what may become the highest-stress job in a company?

Even the most mediocre salesperson is typically good at one thing – selling themselves.  Unfortunately, that doesn’t generally translate into an ability to sell your products or services. This unfortunately renders your normal interview process ineffective. This is further complicated by the experiential fit with the stage of your company.

The only way we’ve found to increase the probability of hiring is to more deeply engage with the candidate to better understand how they approach the sales process and fit with your company culture. So, after you’ve narrowed your candidate list down to the most promising, here are some things that you can try to reduce the risk of making the wrong choice:

Request a 30/60/90 day plan

This isn’t intended to be a full sales plan; rather, a view into how the candidate approaches new challenges and their sense of urgency, and when the company can expect to see results.  If this plan is heavy on preparing-to-sell activities vs. actually selling, your antennae should go up.

Drill down on compensation

You’ll have a budget number for on-target compensation.  Once you and the candidate agree on total compensation, ask them what mix of salary and commission they would deem acceptable.  If their response is biased towards base salary, your antennae should go up.

Discuss how to define success on a timeline

A quota, sales qualified leads (SQLs) and closing rates are all valid key performance indicators (KPIs). For instance, if you’re hiring a killer and the candidate defines success too tangential to quantifiable top-line impact or don’t square the company’s timeline, your antennae should go up.

Be sure to scrub their LinkedIn and weave what you learned into the conversation.  Ask questions like:

So, when you were selling for Black Ice what was your quota?” 

“How much did sales increase during your tenure?” 

“What marketing budget other resources supported your sales efforts?” 

“What was the culture like at Black Ice when you worked there?” 

“Why did you leave?” 

This info could help you determine cultural fit. If there is a stage mismatch or if you simply cannot afford to support the candidate to the extent that is required for success, your antennae should go up.

Look, there is no surefire to hire the right salesperson that gels with the stage of your company. But the thoughts above will help you reduce the risk of making a costly hiring decision.