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Articles, podcast, and events, organized by topic so you can find what you need instead of scrolling for it. No recycled LinkedIn takes. Every claim here gets tested in a live deal first.

Break the Cycle

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Roundtables and workshops for people who want to do the work.

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2026 Field Guide

The State of Sales Careers

Read where we stand, build our next 30 days, and prepare for what changes next.

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Sales Talent & Careers

Hiring, Building A Career, And Why We Exist.

8 articles

How to Hire Our Own Boss in Our First or Second Sales Position

We are never only accepting a job. We are choosing the manager who will shape how we learn, work, and grow.

Career Change Into Sales: How We Hire Our Next Boss Without Starting Over

A practical guide for changing careers into sales by translating our experience, proving our skills, and hiring our next boss inside a durable company.

After a Sales Layoff: How We Choose Our Next Boss and Rebuild

A practical 30-day plan after a sales layoff to stabilize our search, rebuild proof, and choose our next boss with more clarity.

Our First Sales Job After College: How We Hire the Manager

A guide for recent college graduates hiring a first sales manager by evaluating the customers, training, quota math, and durability of the business.

Hire Slow, Fire Fast: The Company’s Side of Hiring Our Own Boss

A hire-slow, fire-fast framework for profitable sales teams with clear role math, structured evaluation, strong onboarding, and humane decisions.

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Sales Leadership

Reinforcing And Diagnosing The Team.

19 articles

Stop Promoting Your Best Sales Reps Into Management

A study of 1,500 promoted sellers found team sales fell 7.5% on average under former top performers turned managers. What to promote on instead.

Why Your Best Sales Rep Is About to Quit (And It's Not About Money)

New 2026 data: leadership and culture outrank pay 2-to-1 as the reason top performers leave, and the warning signs show up months early.

Sales Culture Doesn't Show Up in the Good Quarter

What eight episodes of Break the Cycle prove about accountability, forecasting, and the pressure test culture actually has to pass.

How to Reduce Sales Team Turnover Without Lowering Expectations

Fix the operating conditions that push capable sellers out.

Why Sales Managers Need a Coaching System, Not More Pipeline Meetings

A weekly method for turning observation and practice into better seller behavior.

The Forever Churn

The labor market went quiet. Sales turnover didn't. Why 35% annual churn is a quota design problem, not a talent problem.

What Should Sales Enablement Actually Own?

Enablement is not a junk drawer for every problem nobody else wants. Six areas it should own, and the ones it shouldn't.

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Sales Coaching

The Fundamentals That Don't Go Out Of Style.

30 articles

Three Sales Non-Negotiables for Every Call

No exceptions, no matter how the call is going. Three of the five non-negotiables from Break the Cycle Episode 13, before the full list drops.

Five Sales Questions That Actually Move a Deal

The Columbo Close, the pocket full of yes, and the question that makes buyers do the ROI math themselves.

Three Sports Rules That Can Transform Your Sales Performance

Effort, teamwork, and fun competing. The same three rules I teach my kids in sports work in sales too.

Let's Make Average Impossible: Your Deal Isn't Stuck, It's Single-Threaded

Stalled deals are usually a multi-threading problem, not a ghosting problem. How to fix it before quarter-end.

Why I Don't Trust Sales Reps Who Never Struggled

Struggle builds the resilience great reps need. Why I hire and coach for it instead of avoiding it.

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Selling With AI

Using AI Tools Without Outsourcing Judgment.

7 articles

How to Run AI as a Sales Team Without Creating Automated Chaos

A framework for deploying AI across a sales team with approved data, human review, and measurable outcomes instead of automated chaos.

What Does It Cost to Run Claude as an AI Sales Rep?

A token-level cost model for running Claude as a sales rep, built on current API pricing and the costs most companies miss until the invoice arrives.

Gemini for Sales: Turn Google Workspace Into a Better Selling System

How to turn Gmail, Docs, Sheets, and Drive into a working sales system with Gemini, without losing the seller's judgment in the process.

ChatGPT for Sales: Ten Workflows That Save Time Without Outsourcing Judgment

Ten ChatGPT workflows for account research, discovery, call review, follow-up, and coaching that save real time without handing over the judgment calls.

You Are Probably Evaluating the Wrong Vendor

Most AI vendors solve step one and call it the whole job. How to evaluate for the hard tier, not the demo, across every seat at the table.

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AI & The Workforce

What's Actually Changing, Beyond The Hype.

22 articles

AI Agents Are Running Your Law Firm

A federal judge just ruled that a consumer AI tool destroyed attorney-client privilege. What every firm needs to change now.

The Great Decoupling: Why the Era of Seat-Based Software Is Ending

Seat-based SaaS pricing is collapsing as AI agents replace licensed users. What the shift means for vendors and buyers.

Software Is Human, Part 2

Enterprise architecture is being rewritten as software starts performing labor instead of just supporting it.

AI Is Not a Feature. It Is a Workforce Shift.

Most executive teams are not confused about AI. The problem is not awareness. The problem is framing.

The Death of the Phone Tree

The economics behind IVR's slow death, and the 24-month roadmap most call centers are already on.

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Sales Training & Process

Choosing, Measuring, And Running The System.

15 articles

How Much Does B2B Sales Training Cost?

A real breakdown by team size and deal complexity, and why the real number is bigger than the invoice.

A 30-60-90 Day Sales Onboarding Plan That Builds Real Performance

Turn product information into skill, judgment, and increasing independence.

How to Run a Win-Loss Analysis That Produces Better Decisions

A closed-lost report full of labels is not an answer. A real win-loss process using buyer interviews is.

How to Negotiate B2B Sales Deals Without Giving Away the Deal

A discount is not a negotiation. How to trade concessions, protect value, and know when to walk.

What Makes a Sales Workshop Actually Work

A good workshop fixes one problem in one room in one day, and it only sticks if someone reinforces it after the room empties.

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"Sales is still a numbers game. But the prospect on the other end isn't just a number."
Phill Keene

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