“Success is a menace. It fools smart people into thinking they can’t lose.” ­­

— Bill Gates


How can a sales professional best choose their next employer? There is a cliché that a good salesperson can sell anything, but it isn’t really so.

In the real world, even great salespeople can fail in the wrong environment, even selling products they have had great success with in the past. How can a salesperson best position themselves for success when job hunting?

Here is specialized advice for four categories of sales performers — high performers, medium performers, low performers and newcomers — in positioning themselves for success:

High performers

Selling yourself as a high performer is the easiest job search there is. If you sell more than your quota year after year for a large stable company, you probably won’t be on the market much — why should you be? Sometimes large-company super reps look for roles elsewhere when their employer gets penny foolish and starts lowering compensation escalators for those handful of reps who hit the ball out of the park. This rarely ends well for the employer.

First-tier reps who specialize in early-stage companies are more likely to move around. In my experience, they are ruthless in assessing whether a potential employer has potential for them to make their numbers and will reject any that are not a fit or not well-funded.

This ruthless quality in assessing firms is sometimes all that separates superstars from above-average performers who listen to the siren songs of entrepreneurs who are better at promoting than executing their vision.

Medium performers

A medium sales performer makes quota some years, misses it in others. Often, they are first-rate account managers who aren’t quite as aggressive as the high performers. They may be more distracted intellectually, as opposed to the top performers whose self-worth is directly dependent on making and exceeding their quota.

For medium performers, be aware of your strengths and limitations and don’t put yourself in roles that are exciting but ultimately unstable platforms for successfully selling.

Low performers

If you have had results ranging from mediocre to bad, you might have the makings of a successful account manager. What is the difference between sales and account management? In both cases, you are responsible for corporate revenue, but account managers are farming, not hunting.


It is difficult and somewhat rare to step directly into a blue-chip key account sales role with no selling experience.

The path to a B2B key account sales role tends to have these steps:

Inside sales: Phone salespeople who respond to warm leads collected digitally or cold call to set up appointments with targeted prospects for key account reps. Often add-on products to a major product sale are sold exclusively by phone, creating a path to the key account rep role.

Pre-sales engineer/account management: If you have depth of experience in the product or service, you may be added to the sales team and given the opportunity to learn to hunt. It is less likely to happen in a new company.

“Minor leagues”: It is difficult to get a first job calling on clients for a tier one company. Fortunately, the economy is full of second- and third-tier companies. They often have products with mediocre value propositions. Taking a job with one and trying to make quota for a year or two will often be enough experience to be hired into a better company.

For all experienced people, it is prudent to be leery of companies that have the following attributes:

• 1. Companies that do not have a clear product set.

• 2. Small companies that have never had a successful salesperson aside from their founder or a partner rainmaker.

• 3. Companies that do not support the sales team in the same way your past successes did.

In my consulting, I often work with early-stage companies with products that are innovative and still being refined. Salespeople are hired and fired one after another when they do not match the productivity of the founder. Then those same individuals are hired by first-tier companies like Oracle or Microsoft where they are productive employees over a long period of time.

Why are they successful in the larger company framework? The individual didn’t change — rather the new employer has a process and organizational framework that asks the salesperson to do a couple of things well, rather than compensate for product ambiguity, lack of sales support, or unrealistic expectations by an expert founder who is a rainmaking unicorn.


Isaac Cheifetz is an executive search consultant focused on leadership roles in analytics and digital transformation. Go to catalytic1.com to read past columns or to contact him.