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

I recently found out that our win rates jump from 42% to 68% when we are multi-threaded across THREE or more people. 

Access from one to two people makes no difference. 3-4 is where we make our money.

This led us to codify five multi-threading "plays" we now use based on the situation. Here they are for you to steal or experiment with.

Register for the 2025 Skill Stacker Awards contest and ceremony here: https://www.pclub.io/skill-stacker-awards

In this episode, Chris Orlob announces the first annual SkillStacker Awards, a contest designed for B2B sales professionals. The awards will recognize top sellers, transformational stories, and various categories within the sales profession. The event will kick off on February 13, 2025, with opportunities for participants to win prizes, including a trip to Fiji. Chris encourages listeners to join the live event and highlights the importance of recognition in the sales industry.

Takeaways

The SkillStacker Awards are open to all B2B sales professionals.

The contest will run throughout 2025, culminating in an awards ceremony.

Categories include top sellers, rookie of the year, and mentor of the year.

Participants can win a trip for two to Fiji for the best success story.

Recognition can enhance a sales professional's resume and career.

The event will feature success stories from 2024.

Chris emphasizes the fun and competitive nature of the awards.

Joining the email list is crucial for updates and participation.

The awards aim to celebrate skill transformation in sales.

This initiative will be an annual event, building on its success each year.

In this episode, Chris Orlob discusses the importance of setting clear revenue goals for 2025 and the math behind achieving those goals. He emphasizes the need for sales professionals to calculate their required opportunities and contacts to reach their desired income, while also highlighting the significance of clarity in motivation and success in sales.

Takeaways

People are feeling cautiously optimistic in the sales world.

Setting clear revenue goals is crucial for success.

Calculate how much revenue you want to close.

Understand your average deal size to determine the number of deals needed.

Identify your close rate to calculate required opportunities.

Break down annual goals into monthly and weekly targets.

Reach out to a specific number of contacts to generate opportunities.

Improving sales skills can positively impact conversion rates.

Clarity in goals enhances motivation and performance.

Sales success is a simple math equation when broken down.