Losing a deal over a calendar link?!

Published: Wed, 05/06/26

Updated: Mon, 05/11/26

May 6, 2026

TOGETHER WITH

Good morning, Quota readers. Now we’re in May, so make sure you’re all stocked up on your allergy medicine. In this week’s histamine-induced issue, we’ll take a look at the history of the door-to-door security salesman. After that, a Fail about a calendar link, and then some advice for a rep who can’t seem to unplug. Let’s go.

NUMBER OF THE WEEK

40%

Every 4 years, around 40% of LinkedIn members change their industry, seniority, and function

Source: LinkedIn

SALES ROUNDUP

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

A saleswoman known as the 'royal rat catcher' at the pest control firm she worked at has won a lawsuit over changes that sabotaged her £105,000 commission. Dawn Piper had to quit her job at Rentokil Initial after her bosses refused to change a new scheme which threatened to take away the commissions that made up the vast majority of her income. As a veteran sales manager, she personally netted her company up to £850,000 a year for three decades, an employment tribunal heard. Ms. Piper would usually make around £150,000 a year with her commissions. You can read more about it here.
Houston-based auto giant Group 1 Automotive has executed a major belt-tightening move, cutting nearly 700 U.S. full-time jobs in early April as part of a broad cost-reduction campaign. The layoffs hit both dealership-level roles and corporate staff as leadership works to rein in selling, general and administrative costs, while saying it is protecting revenue engines like parts and service. On an April 30 earnings call, executives told investors that the early-April actions reduced headcount by nearly 700 and trimmed about $14 million in annualized contract and vendor spending. You can read more about it here.

FEATURE

The Rise of the Door-to-Door Home Security Salesman

In 1853, a man named Edward Callahan was working as a telegraph operator in New York when he came up with an idea: what if a business could send a signal the moment something went wrong? He built a system that connected buildings to a central monitoring station using telegraph lines. If a door was opened or a window was disturbed, a signal went out.

That idea became the foundation for what would eventually turn into ADT—originally the American District Telegraph company. In the beginning, it wasn’t about homes. Banks, warehouses, and rail depots were the customers. Places that had something worth stealing.

And home security didn’t really become a business until much later.

By the 1960s and 70s, the U.S. had changed. Suburbs had expanded quickly after World War II. More people owned homes, and more people had things inside those homes they considered valuable. And crime—at least as people experienced it through news and word of mouth—felt like it was rising.

That’s when companies like Brink's and ADT started pushing into residential markets. To do this, they sent salespeople.

The pitch was straightforward. A rep would knock on your door and ask a few questions: Do you lock your doors every night? Do you travel? Do you have kids? Then they’d walk you through how easy it would be for someone to break in. Sometimes they’d point out a side window or a sliding door. The sale used fear and psychology.

Then they’d offer the solution: a system that connected your home to a central station, staffed 24/7. If anything happened, someone would know immediately and could send help.

The systems themselves were basic by today’s standards—magnetic contacts, motion sensors, and loud sirens. But the real product was the monitoring contract. The companies made money through monthly recurring revenue, decades before SaaS made that model famous.

The in-home demo became a core part of the sale. Reps would show how the alarm triggered, how quickly the signal went out, and how loud the siren was. Some reps carried portable units. Others relied on storytelling— “A family down the street just had this happen…”

It worked because it hit something specific: responsibility.

By buying a security system, you were doing everything you could to protect your family.

By the 1980s and 90s, the model had scaled. Door-to-door sales teams spread across suburban neighborhoods. Commissions were high, while the barrier to entry was low. Some reps treated it like a career, while others came through for a summer, knocked on a few hundred doors, and left.

At the same time, the technology improved. The systems became more reliable, and monitoring centers expanded to keep up with demand. Branding also got stronger. The ADT sign on the lawn became part deterrent, part status signal. It told people something about you and how you lived.

Then, in the 2010s, companies like SimpliSafe and Ring changed the model once again. There were no contracts. You could install the product yourself. And everything worked off an app on your phone. You didn’t need to deal with a salesperson in your home anymore. You could order everything online in ten minutes.

But there are still reps knocking on doors, especially for bundled offers—security plus solar, security plus smart home packages. The script now is less focused on fear, and more focused on convenience. The structure, however, remains the same: find the gap, make it feel real, and close it.

From a telegraph wire in 1853 to a push notification on your phone—an entire sales industry has evolved.

Your Team Can Make Meetings Optional. Here's How.

Sales reps spend nearly 100 minutes a day switching between apps — time that should go toward closing deals. Meanwhile, the meetings meant to keep deals moving often slow them down instead.

Slack changes that. When your Salesforce data lives alongside your team conversations, you can make decisions in real time with no status meeting required. Reps see customer context the moment they need it. Managers get visibility without another sync. Deals move 4x faster when everyone is connected in one place.

Less time in meetings. More time selling. That is the idea behind 10 Ways to Make Meetings Optional with Slack, a practical guide to reclaiming your team's most valuable resource: time.

Download the ebook

MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

What was the best year for total vehicle sales in the U.S. from 2005-2025?

A. 2024
B. 2012
C. 2016
D. 2021

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 commercial cleaning services. I had a prospect a couple months ago. The guy owned a dental practice. We’d spoken once. It was a good conversation. He seemed normal. At the end, he said, “Shoot me a couple times next week and we’ll take a look at the place.”

Instead of just sending times, I replied with my scheduling link. I figured it was easier. It’s what I always do.

He wrote back about fifteen minutes later: “I asked for your availability, not homework.”

Uhhhhhh. Okay…

I sent over a few times right away and apologized, but he didn’t respond. A few days later he emailed saying he was going to stick with his current company. Cool.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- May 2026

WORTH A PEEK

Which non-SaaS sales jobs offer a decent base pay? This question was recently posted to Reddit, with some good responses. You can 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).

Dear Quota Team,

I always feel guilty taking time off because I know my pipeline will suffer. Basically, I can never enjoy my vacations. How do people actually unplug in this job?

Always On in Location Withheld

Dear Always,

The harsh truth is most top performers never fully unplug.

But you can set yourself up for a better time. Before you go, prep everything. Get as much work as possible done ahead of time. Make sure nothing important is sitting there waiting on you.

While you’re out, give yourself time to check once a day. A ten minute window just to make sure nothing’s on fire.

Bottom line: don’t wreck your health in pursuit of quota. Find a balance that works, even if it’s lopsided.

Quiz Answer: C. 2016 was the best year for total vehicle sales in the U.S. between 2005-2025 (you can read the source article here)

How did you like today's story?

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

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