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, they dig into why cold calling is more defensible than ever (hint: it's not just about volume), KD's problem-based versus value-based call frameworks and how to know which to use for which persona, the exact opener structure that earns a 65–70% yes rate, and the counterintuitive meeting-booking tactics, including why asking for tomorrow's meeting kills more deals than it books.

Check out KD's Courses on pclub

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 lead enablement, run a revenue org, or sit on a board asking why your enablement spend isn't showing up in the P&L, this one's a gut-check.

Chris explains how AI is finally making skill and capability measurable, why that single shift rebuilds the entire power structure of the function, and what it sounds like when an enablement leader walks into a QBR speaking the language of dollarized skill gaps instead of training completion rates.

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 consequences that follow each problem you solve or persona you sell to, then lead with those consequences as a point of view.

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 stop scrolling and actually reply.

Kyle walks through the exact 5-step framework he's used to train SDR teams on POV-led outbound, why "signal monitoring" without interpretation is just dressed-up spam, and how he scaled this approach at Clary to triple qualified pipeline while sending 25-30 emails a day instead of thousands.

If you're a sales leader watching your team's reply rates collapse under the weight of AI-generated noise, this episode is the antidote.

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, and unpredictable pipeline generation no matter how much tech you stack on top.

In this episode, Chris walks through the 2026 State of SDR Skills Report - the 10 skills defining the new standard of SDR performance - built with input from an industry council including Kevin Dorsey, Kyle Coleman, Kyle Norton, and Emily Worrell.

If you lead an SDR or pipeline gen function, this is the diagnostic lens you've been missing.

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 performance system (not an HR exercise) is the missing piece behind every great sales process.

A practical breakdown for revenue leaders, founders, and frontline managers who want to operationalize excellence.

Chris Orlob breaks down seven lessons from personally closing a multi-six-figure deal with the CEO of a $1B+ company - in under 30 days.

From positioning that made the CEO come to him, to leading the buying process, diagnosing instead of discovering, and why opinionated proposals win at the top.

A tactical playbook for anyone selling complex deals to senior executives

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 "just hire a rainmaker" strategies produce a few big deals and then stall.

Chris organizes the 11 skills into three pillars: unlocking, navigating, and closing the enterprise deal and turns the episode into a diagnostic you can run against yourself or your team.

Identify four-plus gaps and your upmarket motion is already at risk; six or more and it'll break before it gets off the ground.Timestamps

• (00:50) Why most upmarket attempts make the business worse
• (04:43) The acid test: what "going upmarket" actually means
• (07:30) The 3 pillars and how to use this episode as a diagnostic
• (08:30) Skills 1 & 2 - Multi-threaded and multi-channel prospecting
• (13:00) Skill 3 - POV formation (with the HubSpot inbound example)
• (17:30) Skill 4 - Discovery that creates value, not just takes it
• (22:00) Skills 5 & 6 - Champion development and access to power
• (27:00) Skill 7 - Economic buyer alignment (not approval)
• (31:30) Skill 8 - Mutual action plan orchestration
• (35:45) Skill 9 - CFO-worthy business cases
• (39:45) Skill 10 - Navigating enterprise closing motions
• (43:00) Skill 11 - Negotiating with business acumen
• (45:30) Why you can't hire your way into the enterprise

Welcome to the Caliber Show, a reset and a rebrand.

In this opening episode, Chris Orlob unpacks why 84% of sales training initiatives fail to produce lasting behavior change, and walks through the 15-step operating system elite revenue teams use to durably upskill sellers, install reinforcement, and reduce performance variance across the org.

Tune in every Monday and Friday morning for the latest Caliber Show!

Welcome to Revenue Rewired!

The conversation delves into the shift in demand from positive to negative, impacting the sales environment and requiring upskilling of sales reps and leaders. It explores the importance of building sales skills and systems, selling against the competition, and providing consistent and daily reinforcement. The traits of elite sales reps, the use of volume, signal data, and outbound strategies, the art of discovery, and the screening of traits in sales reps are also discussed.

Takeaways

• Demand has shifted from positive to negative, requiring sales reps to upskill and leaders to be more cognizant of their teams.

• Top 1% of reps control the deal, set the agenda, define next steps, and force clarity on the decision process.

• The best sales reps ignore internal and deal noise, focus on high-value selling conversations, and qualify opportunities ruthlessly.

Chapters

• 00:00 The Shift in Demand and Upskilling

• 05:07 Selling Against the Competition

• 10:46 Traits of Elite Sales Reps

• 22:15 The Art of Discovery