HeyJaredGetting to Club
The podcast that will help you become or stay a President's Club winner in tech sales by stealing the playbooks and skills of the top 0.01% of tech sales practitioners and earners. New episodes Monday, Wednesday, and Friday.
- Indexed episodes, last 90 days
- 4
- Latest publication
- Sep 25, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 31, 2026
Latest episodes
The "Questions That Sell" Summit (opens the original)
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Why do some sellers get executives talking openly while others hit discovery fatigue in the first five minutes? In this summit session, Chris Orlob, CEO of Caliber, shares new Caliber Index data from about 300,000 AI-analyzed calls across 1,592 AEs. It points to one overlooked skill: strategic synthesis, which means handing buyers their problem back sharper and clearer than they gave it to you. Top sellers are 69% stronger at it than average reps, yet only 17% score strong or higher.
Issue 001 - The Caliber Index (opens the original)
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Download the first issue of The Caliber Index HERE! https://drive.google.com/file/d/1K8f2nyv7wFWFKFLUgtt8FkgUvZ9TGS1X/view?usp=sharing
LIVE Insider Deal Strategy On An Eight Figure SaaS Deal (opens the original)
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Listen to Chris Orlob advise and strategize on an 8-figure SaaS deal - live coaching call!
Three Non Negotiable to Become So Good They Can't Ignore You (opens the original)
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What do you do when your buyer's economic buyer alignment is rock solid but one gatekeeper has quietly torpedoed three prior deals? On this episode of The Caliber Show, Chris Orlob works live through real rep deals: managing scope creep when a prospect's vision suddenly expands using the PAPR framework to map stakeholder resistance, and knowing when "enough discovery" becomes overkill. A masterclass in reading the room and asking the uncomfortable question before it costs you the deal.
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