Practical AI Strategies for B2B Sellers and Sales Leaders with Jason Tsai

AI has moved past the “is this real?” phase—and entered the “who’s actually adopting it well?” phase. In this episode of the My Sales Day podcast, Michael Hess sits down with Jason Tsai (joining from London) to break down what AI is actually doing inside modern sales orgs, where teams are still stuck, and how B2B sellers can use AI to sell more—not just produce more “work.”Jason shares the career path that led him from media planning to digital transformation roles, and ultimately into AI enablement at Pivotal, a growth studio that doesn’t stop at strategy decks—Pivotal embeds with teams to implement change and drive adoption.From there, the conversation gets practical:Why AI tools are mature, but adoption is unevenHow sellers go beyond basic “write my email” prompts into scalable prospecting and enrichmentHow AI helps verticalize value propositions without breaking brand governanceWhere AI is useful for role-play, objection handling, and pressure-testing messagingThe difference between using AI to produce “work slop” vs. using AI to sharpen performanceWhy the transformation is only half tools—and mostly human motivation, training, and habitsIf you’re a seller, manager, or sales leader trying to figure out what to do next—this is a grounded, non-hype roadmap for using AI to reclaim selling time and raise the bar on how you prepare, message, and execute.Featuring: Jason TsaiHost: Michael Hess, MySalesDay PodcastTimestamps00:18 Welcome + first MySalesDay episode of 202600:40 Jason joins from London: “neither sunny nor dry”01:23 The mission: tangible AI action items for sellers and leaders02:10 Jason’s career arc: agency → publisher → Visa → ad tech → AI04:03 Falling down the AI rabbit hole + the “no time to learn AI” insight05:49 What Pivotal does: operator-led growth studio, implementation not slides06:02 Jason’s team: AI enablement, workflow mapping, “robots” that speed up real work08:32 Agenda: state of AI, skills impacted, adoption resistance11:04 Where AI is today: beyond experiments, now “uneven adoption”12:09 Sales AI example: Gong and what call data reveals13:35 The 30% problem: sellers spend too little time actually selling15:27 Leveling up prospecting: from ChatGPT searches to scale tools16:19 Scaling research + enrichment: Clay/Apollo-style workflows18:05 AI and value proposition: customization at the account/segment level21:37 Governance: using AI to grade/pressure-test messaging before it ships25:01 Negotiation prep: scripts, simulations, and objection handling practice30:28 In-meeting AI: awkward live, powerful for preparation and post-call learning48:13 Adoption resistance: tools are half the equation—humans are the rest49:30 How to drive adoption: make it role-specific + prove time savings51:24 Close: better habits equal better sellingHosted on Ausha. See ausha.co/privacy-policy for more information.