085 – Enterprise Sales: Painting the Picture of What’s Possible | Doug Landis

085 – Enterprise Sales: Painting the Picture of What’s Possible | Doug Landis

Doug Landis (@douglandis) spent more than 12 years driving sales productivity and efficiency inside some of the world’s top technology companies such as Google and Salesforce. Doug has carried numerous titles most notably Chief Storyteller at Box where he helped transform the way sales reps talked to their customers leading to sales of more than $300M annually. Another title worth googling is his stint as a reality tv star.

Now a venture capitalist at Emergence Capital, Doug still finds he’s a salesperson at heart. He’s inspired to elevate the sales profession and teach reps how to sell to an executive at an enterprise level. In his current role, he focuses on consulting companies to go from 10 million to 100 million by honing in on three key things: focus, hiring, and customer success.

Doug shares that to sell to a CEO, you have to be able to have a business implication conversation, not a product or capability conversation. The role of the salesperson is to articulate a vision of what is possible using the stories of their customer’s successes.


  1. Raise Your Business Acumen: Selling into the C-Suite of enterprise companies is more education than pain-based. They know the problems they have and they’re looking for salespeople to rethink what’s possible. This has nothing to do with your product features and benefits and everything to do with their business. You need to be able to quickly identify your value and show a direct correlation to their pressing issues.
  2. Define the Trigger Moments of Custom Success: When it comes to customer success, it’s not enough to just get your customer to the point of that they can’t live without your product. What you need to really dig into is why they can’t live without it. What are those trigger moments that get them to go from exploring to needing to not being able to live without it?
  3. Have the Conviction to Say “No”: Lose the happy ears. Not everything is a good opportunity for you or your company. Could you potentially lose a deal with this approach? Damn right, you might, but the level of respect you’ll gain will trump the potential loss. Knowing your value and the impact it can have on an organization will help you build that confidence.

Book Recommendation


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

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