On this episode of Oh Frac!, host Adir Ron sits down with Jack Oliphant—endurance athlete, former CBSi/Vox/Acast rain-maker, and self-proclaimed “fractional generalist.” From finishing an Ironman to shepherding multimillion-dollar ad products, Jack now blends RevOps, sales leadership, and operational strategy for seed-to-Series D startups. Tune in for a candid look at why CRM is a fractional’s best friend, how LinkedIn can both fuel and fool your pipeline, and the drama of a cap-table recap gone sideways. Whether you’re a founder weighing fractional talent or an exec eyeing the leap yourself, Jack’s hard-earned lessons on pacing for the long game will leave you ready to race.   Key Takeaways: * Endurance training parallels fractional life: dream → train → race mindset * “Fractional generalist” = RevOps glue across sales, marketing & CS * CRM first, always—start tracking relationships on day one * HubSpot is now a legit enterprise rival to Salesforce for many scale-ups * Weekly Loom video updates keep clients aligned & personal * Partnerships (e.g., Domestique) expand reach without sacrificing solo freedom * Cap-table recaps: emotionally charged but rich in board-level lessons * Retainer-based scopes beat hourly billing for strategic work * Build your ICP early to filter ideal clients and engagements * Fractional market likely to grow beyond 10 % of U.S. workforce in 5 years   Chapters: 00:00 Welcome & Jack’s intro 03:30 Ironman mindset meets fractional work 08:00 From CBSi → Vox → Acast → solo founder 12:30 Million-dollar ad product & risk tolerance 16:30 “Fractional generalist” explained + LinkedIn hacks 21:00 CRM deep-dive: HubSpot vs Salesforce 25:30 Partnering with Domestique for bigger wins 29:30 Frac’d-Up Moment: recapitalization drama 34:00 Quickfire round: myths, tools, dream clients 38:30 Final advice & where to find Jack   Jack Oliphant’s LinkedIn: https://www.linkedin.com/in/jackoliphant/ Jack's website: https://www.oliphantstrategies.com  Adir Ron’s LinkedIn: https://www.linkedin.com/in/adir-ron/   Keywords fractional leadership, RevOps, CRM, HubSpot, Salesforce, startup growth, endurance mindset, Ironman, LinkedIn strategy, cap-table recap, revenue operations, podcasting, fractional CMO, fractional executive