"Fair" territory doesn't exist

Published: Wed, 01/28/26

Updated: Sat, 01/31/26

January 28, 2026

TOGETHER WITH

Welcome back to another snow-blasted edition of The Quota. We’ve dug ourselves out of the storm, and are ready to bring you the latest in sales goodies. In this week’s issue, we’ll look at why territory fairness doesn’t actually exist. Otherwise, it’s business as usual. Let’s go.

NUMBER OF THE WEEK

Companies spend around $20 billion a year on sales training.

Source: ADT

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

Software giant Autodesk has announced they’re cutting 1,000 employees, or 7% of their workforce, mostly from customer-facing sales roles. Autodesk employees were informed of the cuts in a message from CEO Andrew Anagnost on Thursday, January 22. Anagnost stated the enterprise-wide organizational changes come as Autodesk enters the next phase of its multi-year GTM transformation and reflects a decision by leadership to align the organization with its long-term strategy. You can read more about it here.
A Queens man is accused of pretending he was a car salesman to scam a man out of thousands of dollars. According to detectives, Navendra Balisingh, 22, met the victim at a place that wasn't the dealership but identified himself as an employee at Advantage Toyota of Valley Stream. Balisingh is accused of driving the victim to a nearby Chase bank, where the man took out $4,700 for what he was told was a deposit on the car. The next day, Balisingh allegedly reached back out to the victim, asking for more money. You can read more about it here.

FEATURE

"Risk Board Game" by Rob.Bertholf is licensed under CC BY 2.0.

The Illusion of Fair Territory

Every sales org has the same ritual. A spreadsheet appears. Someone says the word “coverage.” Someone else says “balance.” By the end of the meeting, leadership assures the team that territories were designed objectively. Most reps nod. Some don’t.

Territory design is treated like math, but anyone who has carried a quota for more than a year knows the outcome of the year is often decided before the first call is made. Two equally capable reps can finish twelve months apart in performance, reputation, and career trajectory because of lines drawn on a map or names placed in an account list.

That reality is uncomfortable, which is why we keep pretending territory is neutral.

Where the Spreadsheet Begins Lying

Territory models usually start with clean intentions. Leadership looks at revenue potential, account counts, historical spend, geography, and vertical mix. The goal is simple: give everyone a fair shot.

The problem is that every input relies on assumptions.

Revenue potential is an estimate based on past behavior that may no longer apply. Account counts ignore variance in complexity. Geographic balance fails once travel friction enters the picture. Vertical focus assumes buyers behave consistently inside categories that are already outdated.

By the time the spreadsheet feels objective, subjectivity has already done its work.

The model looks fair because it uses numbers. What it can’t show is which accounts are stalled, which are expanding quietly, which buyers are about to churn, and which relationships are already warm.

Territory as a Career Multiplier

Sales careers compound quickly. A rep who lands a strong territory early builds confidence, hits numbers, earns trust, and gets better opportunities next year. A rep who inherits a thin patch misses, resets, and spends the following year digging out.

This is why two reps with identical talent can diverge so dramatically. One is described as consistent. The other is described as struggling. The difference sometimes traces back to account quality and timing, not effort or intelligence.

Once a rep is seen as a top performer, their territory tends to stay safer. Once a rep is seen as risky, they tend to inherit more risk. The loop reinforces itself quietly.

The Myth of the Fresh Start

Annual territory resets are sold as fairness mechanisms. New year, new opportunity. Clean slate. In practice, very little resets. A “new” territory often includes accounts already mid-journey. A “new logo” may have years of context behind it.

Reps feel this immediately. Some open January with deals that have momentum. Others open with cold silence and a calendar full of prospecting blocks. Both are told they started equal.

Why Leadership Accepts the Illusion

If territory fairness were truly enforced, revenue would become less predictable.

Leaders face a tradeoff. Optimize for fairness and accept volatility, or optimize for stability and accept inequality. Most choose stability.

Continuity reduces risk. Known accounts produce known outcomes. Reassigning them introduces uncertainty. That doesn’t mean leaders are acting in bad faith. It means they are optimizing for outcomes the organization rewards. Fairness is valued. Predictability is required.

Why Reps Feel Gaslit

The frustration comes from the mismatch between language and experience. Reps are told territories are even. Their lived reality says otherwise. When they raise concerns, the conversation returns to the spreadsheet. Numbers are cited. Models are defended.

What never appears is context. Who had the account last year? What conversations already happened? Which buyers are actively evaluating? Which accounts are stalled indefinitely.

Those details matter more than any column total, yet they rarely shape the final map.

The Hard Truth

Territories will never be perfectly fair. Selling involves too many variables. Anyone promising true balance is selling an illusion. The real question is whether organizations are honest about the limits of their models and the power territory holds over outcomes.

The Warm Intro Gap - Learnings from 1,300 sales leaders

At the end of 2025, the Commsor team set out to answer two critical questions: 1) why sales teams are missing quota (despite increased effort), and 2) how teams can close the growing gap between pipeline and quota. To find out, they surveyed 1,300+ sales leaders and now they're sharing the results with you.

Commsor's "Warm Intro Gap" guide is officially live and available to you. This is a practical, data-backed guide that breaks down why traditional outbound alone no longer cuts it and how top-performing teams are using warm introductions and referrals to drive consistent results. You’ll learn how to quantify the pipeline-to-quota gap, why warm intros work (and why sellers rarely ask for them), and how top performing teams operationalize their networks with a clear, repeatable approach.

Download the guide to learn how you can close the gap for your own team—and don't forget to join their live webinar on January 29th, where they'll walk through the survey findings and key takeaways.

Download the free guide!

MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

How many DeLoreans were sold in the United States during the company’s brief run?

A. 11,112
B. 14,401
C. 1,790
D. 6,681

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

I sell automation software into small manufacturing shops, mostly owner-operators who like to do business face to face. I had a good first call with this guy who ran a fabrication plant outside town, and at the end of the call, he asked me to swing by the office to talk through next steps. It felt like momentum.

After I walked in, the owner met me and walked me into his office. He sat behind his desk and the only spot for me to sit was on the couch, which was halfway taken up by a giant German Shepard, which he lovingly referred to as “his baby girl.”

I hesitated but decided to sit next to the dog. The dog gave me a low growl as I sat. I tried to start the conversation about next steps when the dog stood up and started barking at me. Loud booming barks over and over.

The owner called out to “his baby” but she didn't stop. I was terrified. Finally he ran over and calmed her down. He asked if I was okay. I said yes. Then he said the deal wasn't going to work. He said that he always trusts his dog and she was “a good judge of character.”

I thought he was joking at first so I laughed. But he was dead serious. He was nice about it, but serious. I realized I wasn't wanted and left.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- January 2026

WORTH A PEEK

Beer or alcohol at sales lunches—a nice Mad Men-style experience, or 2026 professional faux-pas? This was the topic of conversation on a recent Reddit thread, where sales reps of all stripes weighed in. Check out the conversation here.

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

I'm a senior AE selling seven-figure deals at a mid-market infrastructure company. My new manager joined recently from a much smaller startup where deal sizes were maybe $50–100k.

He’s smart and well-intentioned, but his coaching doesn’t map to reality. I get feedback like “create urgency earlier,” “push for faster closes,” or “tighten your discovery,” even when I’m dealing with six-month security reviews, procurement cycles, and committees I don’t control.

When deals slip, it feels like the assumption is execution failure, not deal complexity. I’m struggling to apply advice from someone who’s never run a deal this size. How do I navigate coaching that doesn’t fit without sounding arrogant or defensive?

Experienced in Location Withheld

Dear Experienced,

Your job is to map his advice to reality. When he says “move faster,” respond with specifics: where the deal is blocked, who owns the delay, and what leverage actually exists.

Bring evidence, not pushback. Walk him through one live deal step by step so he can see the constraints. If the coaching still ignores complexity, that's a useful signal. It tells you that you're unlikely to succeed with a manager who is more interested in dictating rather than collaborating.

Quiz Answer: D. Approximately 6,681 DeLoreans were sold in the U.S. (You can read the source article here).

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Today's email was written by Ken Kupchik and Steve Rado.

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