"It's About Raising Good Humans" - LodeStar S1 E24 - Bryan Elsesser

In this episode, Cliff sits down with Bryan Elsesser, VP of Corporate Sales and Partnerships at Pavilion, to talk about AI's limits inside legacy companies, the return of in-person relationships in a GTM motion, and why buyers are done paying for tools. Bryan opens up on how AI compliance and data security are becoming real sticking points as companies bring new tools into their workflows. Publicly traded, legacy corporations feel this the most. Their size and their processes make them slow to move, and the gap between what AI can do and what a big company can actually adopt keeps growing. From there the conversation turns to in-person events. Sponsor spending in the field is accelerating, and Bryan makes the case that as AI takes over the daily grind work, real human relationships become the actual differentiator for growth. The conversation closes on family. Bryan is raising five kids while in law school and running a demanding executive role, and he walks through what makes it work: shared responsibilities between the kids, clear boundaries with his partner, and carving out the late night hours nobody else is using. The discussion also explores: → Why young executives need an AI education to have a future in GTM → Bryan's story about hiking Big Slide with three of his kids during a thunderstorm → What his son Ira learned from the experience About Bryan Elsesser Bryan Elsesser is VP of Corporate Sales and Partnerships at Pavilion, where he works at the intersection of GTM, community, and revenue growth. Alongside his work at Pavilion, he advises companies like Winning by Design on sponsorship strategy. Bryan is also currently in law school while raising five kids, bringing the same operator discipline to his family life that he brings to his work. About Cliff Cliff Simon has spent nearly two decades building and scaling revenue engines, from Fortune 20 enterprises to venture-backed startups navigating the chaos of hypergrowth. He specializes in GTM strategy, revenue operations architecture, and fractional leadership for SaaS companies that need operator-grade execution. HubSpot recognized him as a 2024 Modern Sales Leader, and Pavilion named him a Top 50 CRO to Watch. Before founding Polaris, Cliff served as CRO of Carabiner Group, where he led the company's rapid expansion and successful acquisition by SBI in mid-2024. Today, Cliff advises and serves as fractional executive for multiple high-growth startups, bringing deep expertise in GTM orchestration, RevOps systems design, and AI-ready infrastructure. He's an active leader in the GTM community and hosts The LodeStar Podcast, where he explores the operator realities behind revenue growth with leaders who've been in the fire. About Polaris Polaris is an AI-First RevOps consultancy. We empower the companies that partner with us to drive maximum efficiency in their current processes and technology while augmenting with vetted AI solutions in scalable and repeatable ways. About Lodestar For GTM leaders who refuse to navigate alone. LodeStar cuts through the noise to show you what's working in the industry. Through podcast conversations, newsletters, videos, blogs, and more, you'll get tactical insights grounded in real operator experience.