043 – The Danger of Just Winging It | Scott Cramer

043 – The Danger of Just Winging It | Scott Cramer

Sometimes it takes something as seemingly small as a post-it note to make the biggest sale of your career.

That is the basis for the belief system adopted by sales veteran, Greenlight Guru’s VP of Sales, Scott Cramer, who has literally done everything you can in sales.

From opening new markets, being a sales trainer and managing both channel as well as insight sales to being a VP of sales in multiple companies (including Angie’s List, Delivra and now Greenlight Guru, Scott draws success from being a self-described introvert and extrovert.

His motivation comes down to his family and helping his kids succeed, which circles back to his training and experience as a sales coach.

The time he’s spent helping train reps all over the country can be summed up in one simple concept: winging it doesn’t work. What began with an aspiration to manage country clubs evolved into a flourishing sales career because he could talk to and get along with people.

How? Scott’s sales success has been built around practice, process and post-it notes.

In the past if he’s been prospecting a company and is nervous about picking up the phone to call the CEO, Scott’s strategy is to write a post-it note with the CEO’s name and phone number, grab a cup of coffee and come back to find the note. It’s a method that has helped get him in the right mindset to make the calls that matter.


  • Stop Trying to Wing It: Just because salespeople fall under the category of “influencers” doesn’t mean they’ve earned the right to wing it. Buyers will let you own the process if you’re willing to. Meaning if you have a structured process, if you’re working someone through a pain funnel and articulating your next step, your audience will typically let you work. It’s when you try to just ‘wing it,’ that the system breaks down and you ultimately lose control over the sales process.
  • Know Your Weaknesses: Scott mentioned there being five major weaknesses that every salesperson has in some capacity. Need for approval, fear of rejection, low money tolerance, non-supported buy cycle and record collection. Knowing where you sit in each of these allows you to seek the coaching or mentorship needed for growth.
  • Understand Your Identity vs Your Role: All of us have a unique identity comprised of our beliefs, values, principles, desires and emotions. We also have a plethora of roles that we play such as son or daughter, mother or father, friend, co-worker, salesperson, etc. If we confuse the performances in our roles with our identity, our self image can and will go up and down with each success or failure.

Book Recommendations


  • Costello – What if every sales rep inherited the habits of your best rep? With Costello, they do.

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