The Caliber Show

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 ask...

Only 9% of executives say a sales call was worth their time and yet 70% of B2B sellers believe they're better than average. In this episode, we break down the DEPTH Enterprise-Grade Discovery System: a five-part framework for generating real urgency, surfacing business pain that money follows, and closing bigger deals faster.

We cover how to read a buyer's psychological stage in the first minutes of a call, the "Go Back in Time" tec...

A VP of sales at one of the hottest AI companies on the planet did $400M last quarter with 100 reps. Then a $5M account walked, because the rep who closed it couldn't name a single champion or the economic buyer.

Chris Orlob unpacks "skill debt": the liability that compounds quietly while tailwinds blow, then gets exposed the moment the market stops selling for you. We saw it in 2021.

AI is setting up the same trap now, bigger. The m...

You've done the work, built the champion, run a great demo — and then the deal dies at the finish line when a boss you never met says no. This episode breaks down a repeatable, engineered path from champion to economic buyer: a five-step motion for getting to power on purpose instead of hoping it happens.

You'll get the framework for teaching your champion how to actually evaluate (and why you never say the words "economic buy...

Chris Orlob sits down with Nate Nasralla, CEO of Fluent and one of the most-followed voices on enterprise champion development, to dig into the skill that separates reps who close complex deals from those who perpetually await verdicts.

They unpack what actually makes someone a champion, Nate's three I's framework (Incentive, Intel, Influence) and why most sellers are fooling themselves by mistaking advocates for champions.

The conve...

Chris Orlob unveils PClub's newest flagship framework, the Economic Buyer Selling System, in its first-ever public debut.

This isn't a collection of tips; it's a four-stage repeatable system (Activate, Access, Align, Approve) built for AEs and account managers who are tired of running long sales cycles only to watch deals disintegrate at the end because they never had real executive alignment.

Chris opens with a sobering benchmark: a...

Chris Orlob sits down with Kevin Gaither (known in the industry as KG) an eight-time startup operator with three successful exits, including a run as one of ZipRecruiter's first 50 employees as the company scaled to $400M in revenue.

Over 25+ years, KG has built sales teams ranging from zero to 550 people across inside sales, SDR/BDR, account management, and enterprise and he'll be the first to tell you he made a lot of mistakes al...

In this solo episode, Chris Orlob breaks down one of the highest-leverage moves a revenue professional can make: reframing the budget narrative before it gets anchored to the wrong problem.

He walks through a real deal where his AE expanded a $15,000 SKO speaking inquiry into a $50,000 platform partnership in two calls, not through negotiation, but through deliberately reframing the conversation from vendor selection to revenue outc...

Chris Orlob sits down with KD, widely known as the godfather of SaaS sales and modern sales leadership, for a masterclass on the one prospecting skill AI can't touch: cold calling.

KD has helped build multiple companies from zero to eight and nine figures across entirely different industries with zero vertical overlap, and he's developed a cold calling methodology backed by analysis of thousands of real conversations.

In this episode...

Most revenue enablement teams are guilty until proven revenue positive and right now, most can't prove it.

In this solo episode, Chris Orlob breaks down why "vanity enablement" is about to go the way of vanity marketing, shares two real stories of CROs and CEOs taking a hacksaw to their enablement orgs (17 people cut to 4, 6 cut to 1), and lays out the only path forward: re-positioning enablement as revenue risk management.

If you le...

Most sellers were taught to surface a problem and then ask some version of "so how is that impacting the business?"

Chris Orlob argues that question is the fastest way to sound generic, cheesy, and a little manipulative, even when the theory behind it (SPIN's implication questions, building urgency) is right.

In this solo episode, Chris breaks down consequence mapping: a discovery skill where you pre-map the two to three predictable ...

Kyle Coleman has spent 15 years architecting outbound motions that don't rely on volume - first as the founding SDR at Looker, then building Clary's outbound engine from $15M to nearly $150M in revenue, and now as Global VP of Marketing at ClickUp.

In this conversation, Chris and Kyle unpack the difference between personalization (which is now table stakes and largely useless) and a real point of view - the kind that makes a CRO sto...

The SDR role has changed more in the last 24 months than in the previous decade.

AI flooded the market with outbound noise, buyers stopped responding, and an entire generation of SDRs got "developed" through remote work, a pandemic, and almost zero coaching.

The result is a skills crisis most teams haven't named yet - pipeline that looks healthy on the dashboard but doesn't convert, a handful of star performers carrying everyone else...

Chris Orlob shares five patterns he's observed across the most elite revenue organizations after working with thousands of sales teams at InsideSales.com, Gong, and now Caliber.

From maniacally focusing on where you win, to obsessing over narrative, to building rock-solid sales stages with binary exit criteria - these are the habits that separate top-performing teams from mediocre ones.

Plus, why treating skill development like a per...

Going upmarket is the single biggest valuation lever most B2B tech companies have at their disposal and most of them blow it.

In this episode, Chris Orlob walks through the 11 non-negotiable AE skills that separate companies who successfully break into the enterprise from those stuck in mid-market prison.

His core argument: upmarket success is determined by the capability floor of your revenue team, not your best rep, which is why "j...