Lessons from a VP: You Can't Turn a D Player Into an A Player | Craig Holbrook (nCino)

In this episode, I sit down with Craig Holbrook, Vice President of New Client Acquisition Sales at nCino, to talk about what sales leaders actually look for when hiring, coaching, and developing reps. Craig shares lessons from more than a decade in mortgage sales and leadership, including why some qualities simply cannot be coached, why you cannot turn a D player into an A player, and how strong sales leadership starts with understanding what motivates each rep differently. He also breaks down the intangibles he looks for in account executives, including work ethic, curiosity, assertiveness, and attention to detail, and explains why those traits matter more than surface-level interview polish.We also get into coaching, management, and what it really takes for a rep to grow into a leadership role. Craig explains how he evaluates a team in the first 90 days, why he believes in giving reps freedom within a framework, and how he coaches strong performers who are still leaving money on the table because of bad habits. He also talks through how nCino is using AI in its hiring process to analyze assessments, generate probing interview questions, and help identify candidates with the right underlying traits to succeed in sales.TOPICS WE COVER Why some sales traits, like work ethic, curiosity, and assertiveness, are hard or impossible to coach  Why you cannot turn a D player into an A player, and how Craig thinks about developing talent more realistically  How Craig evaluates a new team in his first 90 days and sets expectations with a freedom-within-a-framework approach  How to coach reps who are hitting quota but still have bad habits that are limiting their upside  What separates a strong individual contributor from someone who is actually ready to lead a team  How nCino is using AI in hiring to analyze assessments, generate better interview questions, and improve candidate evaluation ABOUT THE GUESTCraig Holbrook is the Vice President of New Client Acquisition Sales at nCino, where he focuses primarily on the IMB side of the business. He has more than a decade of sales experience in the mortgage industry and has led teams ranging from small startups to large enterprise environments. Earlier in his career, he was a top-producing individual contributor for eight of his nine years in sales and has also led large business development teams across multiple industries.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about nCino: https://www.ncino.com/