Episode 172: The Sales Leadership Gap in the Era of AI with Kristie Jones

Kristie K. Jones works with founders, owners, and sales leaders to build sales playbooks, hire sellers, and scale beyond founder-led selling. She came to B2B software after eight years as a retail buyer for a major department store, took over her first sales team four months later, and has since led teams through the move from on-premise software to the cloud. She is the author of Selling Your Way In: The Playbook for Setting Your Income and Owning Your Life. Her second book, The Sales Leadership Gap: Leading Humans in an AI-Augmented World, releases in late October 2026. Kristie returns to the show two years after her first appearance. She starts with what happened to her first book after it left her hands. She wrote it for individual sellers and hoped it would land in university sales programs. Professors showed little interest, and readers found it anyway, often writing to tell her they had realized they were in the wrong sales role. Her second book began at a crossroads. In June of last year, with business slowing and clients in what she calls freeze mode, she attended six conferences and sat in on every session. Nearly every conversation was about tools. What she did not hear was any discussion of how leadership changes when a sales leader is no longer managing a team of people but a system that includes agents, automations, and humans together. She and Bill talk through what that shift asks of leaders, what she is hearing from senior sellers in interviews, a story from her son about being told to use Copilot, and why the next sales playbook will be written by small groups of practitioners rather than handed down. Connect with Kristie • LinkedIn: linkedin.com/in/kristiekjones/ • Website: kristiekjones.com • The Sales Leadership Gap: available from major book retailers in late October 2026