Strong salespeople fail all the time in new roles.  Good reps, really good reps, that could otherwise do well, and have in the past.

And it feels like it’s happening more often these days, when in tech at least, frictional unemployment approaches 0%.

Why do good reps fail at a new role? Often, they simply pick wrong. And the faster people jump to new roles, and jump around, the higher the odds they may mis-jump.

So here’s a quick 9 point checklist to help you as a sales exec pick better:

  • It’s important first to understand, do you need to be in an environment with lots of training, systems, process, and micromanagement? Big Companies, at least some of them, are generally very good at this. Larger, fast-growing start-ups often become excellent at it. Small start-ups are almost always terrible at it. Don’t join a company of less than 100 or maybe even 200 employees if you need this infrastructure. Most of us do.
  • Pick a price point you know how to sell at. I’ve seen sales reps great at $20k deals join a start-up with tons of leads but at a $2k price point and fail. And vice-versa.
  • Pick a sales process you are comfortable with. Are you good at in-bound? Out-bound? Farming? Account management?
  • Can you do truly competitive sales? Many sales professionals can win in an environment like Salesforce or Twilio where you have a dominant — not sole, but dominant — brand, but melt in an environmesnt that is hyper-competitive. One is not harder than the other. It’s just different.
  • Can you sell without a brand backing you? Related to the prior point. Selling a product without an established brand, at least a mini-brand in its niche, is different. It can be fun because you get to interact with early adopters — but it’s different.
  • Do you or at least can you believe in the product? If you don’t truly believe, it will be really tough to hit quota.
  • Do you or at least can you understand the buyer?  Not everyone is ready for highly technical or highly verticalized sales in the early days of a start-up’s life.  Later, once a company has 30, 50, 100 reps … they have to figure out how the product can be sold without domain expertise, or a technical background, or experience in the industry.  But make sure you can really sell to the buyer.
  • Can you self-organize? It can be very tough to excel in almost any smaller environment if you can’t self-organize. But larger sales organizations put sales operations processes in place that keep you more organized. This may be the #1 reason AEs fail joining very early start-ups.
  • Don’t skip too many steps of development. These days, so many sales professionals skip too many steps. From 60 days as an SDR straight to a quota-carrying AE. From a good AE without ever having hired anyone, straight to a VP of Sales. Push hard, grow faster for sure. But when I see folks skip 2+ stages of development, I’ve almost never seen that work out.
  • Pick a great boss. This doesn’t control for everything, but it sure does control for a lot. A great boss will find ways to backfill your weaknesses, get you trained one way or another, get you into the right role with the right leads. This is #1.  Joining someone who’s never managed a team is always risky (although sometimes worth the risk).  Joining someone that doesn’t have a good sense of why you would join and how the role would help you grow is even riskier.

(note: an updated SaaStr Classic post) and wrong decision image from here

Related Posts

Pin It on Pinterest

Share This