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