In 2008, when Ryan Longfield took a contracted account executive position at LinkedIn without any prior sales experience, he knew he had to be “all-in.” “‘I’ll sleep under my desk if I have to,’” Ryan remembers telling a recruiter who asked if he was worried he won’t be able to hit $50,000 in sales in only three months. Now, after an almost 10-year run at LinkedIn where he worked in five different sales positions, Ryan serves as Chief Revenue Officer of Gong, a revenue intelligence platform for B2B sales teams. On this episode of Go to Market Grit, Joubin and Ryan have a wide-ranging discussion about the importance of pushing boundaries as well as failure.In this episode, we cover:'I was all-in': Ryan's experience as a contracted account executive at LinkedIn in 2008 having never previously done sales — and what motivates him. (2:52)The importance of setting boundaries and creating a healthy work-life balance. (9:46)Why Ryan believes that 'constantly remaining uncomfortable’ is key to career acceleration. (17:10)Learning from the process that led to failure versus focusing solely on the failure itself. (20:43)Imposter syndrome, insecurity, and the benefits of having diversity of perspective. (27:16)Why Ryan believes that quotas should "represent a minimum bar for effectiveness" in sales roles. (37:03)How Ryan's current company, Gong, gives leaders insight into the sales conversations reps have with buyers. (39:17)Coachability; previous history of success; intelligence and business acumen; grit; and curiosity: Attributes of a great sales rep. (48:01)How Ryan defines grit. (51:35)Guest: Ryan Longfield, Chief Revenue Officer of GongLinks:Connect with Ryan LongfieldLinkedInConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins