How to avoid being a creepy salesperson

Published: Wed, 05/21/25

Updated: Tue, 05/27/25

May 21, 2025

TOGETHER WITH

Welcome back to The Quota, the sales newsletter that peaked in high school, but is also having another, smaller, peak later in life. In this week’s glossy (don’t try to touch the screen) issue, we’ll look at the number one biggest problem reps who work at struggling companies face. Then, we’ll share a Sales Fail about the Do Not Call Registry, and give some advice to a rep who thinks their new lead source is creepy. Let’s go.

NUMBER OF THE WEEK

4 - 6

Sandbagging, a common tactic where salespeople delay closing deals to optimize incentives, is a widespread challenge in sales performance management and can reduce sales revenues by 4% to 6%.

Source: Harvard Business Review

SALES ROUNDUP

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

A door-to-door salesman who defrauded women and older adults was recently denied a bankruptcy discharge, according to the Department of Justice. On April 18, the Bankruptcy Court for the District of Oregon entered a default judgment denying a discharge to chapter 7 debtor Jason Gillis. Gillis—who sold vacuums, air filters, and related products—crafted fraudulent schemes targeting women he pursued as romantic partners and their elderly parents. His victims included a 79-year-old woman recovering from a stroke. You can read more about it here.
A former Army office and current sales manager of an outside sales team recently went viral for a TikTok where she explained why she frequently denies her staff’s time off requests. But it’s not what you think—she says she denies the requests because paid time off should be used for vacations and relaxation, not to cover personal emergencies. What a plot twist, huh? You can read the full article here.

FEATURE

The Number One Biggest Problem for Reps at Struggling Sales Orgs

By Ryan Walsh, CEO and Founder of RepVue

Do you feel like you’re selling something your customer doesn’t really need? Ever feel like you’ve exhausted your ideal customer profiles (ICPs) and are now dipping into non-ICP prospects?

The number one issue struggling sales orgs face is this: CAPACITY > TAM.

The Importance of Balancing Capacity-to-TAM

I’ll give you a three-minute crash course: Everything goes really well as a sales organization grows into the market size. But when capacity overtakes the TAM (total addressable market) things become tough and can spiral quickly.

The territories are split too thin. Has your org hit that tipping point yet?

If you have the ability to run a CRM report, you can probably tell.

This is why we see early stage hot startups with really high scores and quota attainment metrics. They’re still growing into their TAM.

But don’t get on board too late. Every company runs out of TAM at some point.

You can see the sales orgs with the highest quota attainment also have great product-market fit scores for that same reason.

When researching a new company — or evaluating your current one — make sure you have a detailed understanding of the TAM, including:

How many prospect accounts are there?
How are they distributed among the existing team?
How do they translate into territories (geo, named, etc)?
How big of a sales team can the current market support?
Where is the org in growth and getting to that team size?
What product functionality is being added to increase the TAM?

You need to ask those questions.

Stay Informed and Be Proactive

You don’t have to wait until you’re stuck pushing products to people who don’t need them. Take the initiative now—dig into your TAM, understand how it aligns with your capacity, and ask the tough questions. Also, leverage the free data by RepVue from sales pros. By staying informed and proactive, you’ll position yourself to thrive even as the market shifts.

Ask questions. Validate. Verify.

Good luck.

MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

What year was Jordan Belfort’s memoir, The Wolf of Wall Street, released?

A. 2002
B. 1996
C. 2013
D. 2007

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 used to sell cars at a good-sized Chevy dealer. Our sales manager was obsessed with follow-up culture and required us to make 50-100 calls a day to past customers or people who'd visited the showroom. One summer, I was working through my call list and reached a guy, let's call him Marshall, who had a test-drive several months earlier. He didn’t answer my first five calls over two weeks, so I left a few voicemails asking about his car search.

Apparently, after my third call, Marshall had phoned the dealership demanding to be removed from our call list. Whoever answered had told him they'd handle it but never updated the system. So I kept calling, completely unaware. Two days after my fifth call, I arrived at work to find Marshall standing across the street with a massive homemade sign reading: "[My dealership name] AND SALESMAN [My name] VIOLATE FEDERAL LAW BY IGNORING DO NOT CALL REQUESTS."

My sales manager panicked and sent me out to apologize. Marshall calmly told me he planned to stand there every day until we "learned to respect the law." Our general manager eventually had to personally apologize and offered him $500 in "inconvenience compensation," which Marshall declined, saying, "This isn't about money." He continued his one-man protest for five straight days—one day per call.

Anonymous Location withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- May 2025

WORTH A PEEK

Depression and sales—how does it go together and what can someone struggling with depression do to maintain performance? This was the topic of a recent Reddit thread, where users weighed in with their own experiences. You can read 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).

Dear Quota Team,

My company recently implemented a visitor tracking tool that identifies everyone browsing our website and alerts me with their name, company, job title, and LinkedIn profile in real-time, expecting me to immediately contact them mentioning their specific browsing activity. Prospects react with obvious discomfort, with one explicitly calling it "invasive surveillance." My sales director insists this is "standard practice" and we're "leaving money on the table" if we don't immediately capitalize on these "high-intent signals," but these don't feel like leads that have expressed interest—they feel like people whose privacy we've violated. Is this tracking technology genuinely ethical in modern sales, or am I right to feel we've crossed a line?

Concerned in Location Withheld

Dear Concerned,

Your discomfort is valid—this technology operates in a gray area. While these tracking tools are currently legal (with websites technically disclosing this capability in their privacy policies), the disconnect between what's technically permitted and what feels respectful to prospects is real. That said, this technology is becoming standard practice, and your competitors are almost certainly leveraging similar insights to engage prospects before you can. Consider a middle-ground approach: use the intelligence to understand which companies show interest, but soften your outreach by referencing industry trends or relevant content rather than their specific browsing behavior—this may help reduce the "creepy factor." If this doesn't work and you're not seeing results, your company may soon realize and abandon the strategy anyway. Good luck!

Quiz Answer: D. Jordan Belfort’s memoir, The Wolf of Wall Street, was published in 2007 (you can read the source article here)

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Today's email was written by Ken Kupchik, Erica Furgiuele, Steve Rado, and Emily Hill.

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