098 – Developing a Game Face for Sales | Kara Gilbert

098 – Developing a Game Face for Sales | Kara Gilbert

Kara Gilbert is the Chief People Person at Turbonomic, a software company specializing in workload automation for hybrid cloud environments, delivering enterprise organizations with automation tools. She has spent nearly 20 years in sales, with experience building high performing teams in rapidly growing tech companies, most recently leading Rapid7 from $20M in sales to more than $100M and an IPO.

Growing up, sports were everything for Kara. Her father, a former professional football player, and coach played a big part in instilling upon her the values of positive attitude, commitment, drive, passion, and training. These all funneled together to create, what she calls, her “game face,” an incredible ability to focus, step up, and be a leader.

Kara believes effort without focus is time wasted. For her, focus requires constant studying and learning. It’s not simply about understanding what is being sold to a customer but learning about who the customer is. By preparing in advance, Kara fosters credibility and authenticity with clients and prospects alike.


  1. Don’t Be Afraid to Work Hard: Just like the quote at the beginning said, winners embrace the need to work hard, where losers see it as punishment. If you want to be great at something, you have to be willing to sacrifice. Just showing up and running through the motions is not going to make you better. Sure, you may have some short-term success, but it’s one of those things where in 10 years, you won’t have 10 years of experience; you’ll have one year of experience 10 times.
  2. It’s Okay to Ask for Help: You don’t have to know everything. Today’s culture seems to be one of needing to memorize answers instead of developing a perpetual curiosity. Don’t fall into that trap. Ask your peers how they do things. Invite colleagues who aren’t in sales to lunch to understand how they impact the business. Ask your customers what really matters to them. Get the notion of “I know” out of your head and start asking others.
  3. Know What Customers Say: Once a company has bought your offering, whether from you or someone else on your team, dive in to understand their perspective. Why did they buy any solution? Why did they decide on your product? What are they hoping to solve? Don’t conflate this with what you do, find out in their words what was important to them.

Book Recommendation


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

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