122: Fun, Focus, and No Duds: Life as a CMO + CRO - with Amanda McGuckin Hager, CMO/CRO at TrueDialog

Recorded IRL at Pavilion’s GTM2025, Washington DC! Amanda McGuckin Hager has worn many hats in her career—sales, marketing, fractional consulting—and today she holds two big ones: CMO and CRO at TrueDialog. After starting out in sales and quickly realizing her heart was in marketing, Amanda built a path through Austin’s B2B tech community, leading teams, experimenting with growth plays, and eventually taking on dual leadership of sales and marketing. In this episode, we unpack Amanda’s journey, her approach to building strong cultures without “duds,” why she’s protective of her CMO title, and how she’s testing AI and search in practical, creative ways. Here’s what we cover:Amanda’s early pivot from sales into marketing (and why it stuck)What it really looks like to be both CMO and CRO at the same timeResetting a sales org from comp plans to quotas to team structureWhy fewer silos and more shared accountability reduce finger pointingHow to spot (and avoid) “duds” when building teamsThe role of fun and positivity in high-performing leadershipFractional marketing lessons: variety, freedom, and choosing clientsWhy Amanda protects the CMO title (even while running sales)Experiments with LLM optimization, long-tail queries, and AI toolsGuarding deep work time with “no meeting” blocks and shitty first drafts Key Links: Guest: Amanda McGuckin Hager: https://www.linkedin.com/in/amanda/ Host: Jane Serra: https://www.linkedin.com/in/janeserra/ Recorded live from Pavilion's GTM2025: https://attendgtm.com/ –– Like WIB2BM? Show us some love with a rating or review. It helps us reach more