Ep. 50: Bottom up and top down 6-figure deal and career learnings featuring Chris Orlob

Episode 50. Thank you for listening this far. More to come!In this episode we welcome Chris Orlob who shares his boomerang journey from seller to startup founder to SaaS sales leader and now back to startup founder. For the deal we cover a recent $110,000 win for his current startup Pclub.io
Background:​Chris identifies more as an entrepreneur than a sales leader, having started his career at InsideSales.com and later founding startups like Conversature and Pclub.io​The deal involved selling Pclub's skill transformation platform to a marketing automation company for $110,000, spanning multiple departments and requiring extensive multithreading.Challenges:​Procurement demanded a significant discount, initially offering a budget far below the quoted price.​Ensuring differentiation and building a strong business case to justify the higher price point against competitors.Key learnings:​The importance of undeniable defensibility, including quantified value, differentiation, and powerful champions.​The value of a multithreaded network and having a compelling event to anchor the negotiation timeline.Timestamps:01:02 – Chris's career journey split across being a seller, leader, and entrepreneur.03:41 – Founding Conversature and its challenges.06:24 – Overview of Pclub's skill transformation platform.08:37 – How the deal started with individual subscriptions leading to enterprise interest similar to PLG model11:03 – Challenges with procurement and the negotiation process.18:48 – Key strategy for successful negotiation: undeniable defensibility.
Resources:Find Chris Orlob on LinkedInThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: Andrew Kappel