Some sales teams are actually growing with AI

Published: Wed, 09/24/25

Updated: Sun, 09/28/25

September 24, 2025

TOGETHER WITH

Welcome to the 201st issue of The Quota! Can you believe we’ve been putting out this newsletter for close to four years? If you’re wondering why we didn’t celebrate the 200th issue, the answer shouldn’t come as a surprise… we forgot! Nevertheless, this week’s issue will deliver the goods, with stats, Fails, and delicious links. Enjoy!

NUMBER OF THE WEEK

15 & 21

The average rep takes 15 questions from prospects, while top performers field 21 questions.

Source: Sales Insights Lab

SALES ROUNDUP

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

A Hong Kong salesman has been jailed for two years and three months for drugging three female colleagues in his home, with the sentencing judge slamming him for inflicting serious psychological damage on his victims. The District Court on Tuesday sentenced 44-year-old Jamie Poon Tik-wai on three counts of administering a poison with intent to injure the three women between December 2013 and May 2014. The court heard the trio were Poon’s colleagues at the local branch of Nu Skin, a US-based cosmetics firm. You can read more about it here.
A Rolex salesman to the rich and famous who was fired after being caught drinking whisky at work has lost an unfair dismissal case. Blaine O’Connor was fired when he was seen drinking alcohol from a can of cola at the Rolex Boutique in Glasgow (UK). The worker would ask his colleagues to pour him a ‘special tea’ — whisky in a teacup so nobody would know it was alcohol. The workers complained about the alcohol consumption, and O’Connor was fired. You can read more about it here.

FEATURE

Photo by Google DeepMind

Some sales teams are actually growing with AI

The sales industry has not been exempt from a common fear: that AI is going to wipe out sales jobs. A recent article in Harvard Business Review pushes back against this notion. For years, analysts and LinkedIn “thought leaders” predicted armageddon, with millions of B2B roles supposedly at risk. The logic seemed airtight. If machines could scrape the data, analyze intent signals, and even spit out personalized pitches, what would be left for the human rep to do?

Yet the opposite is happening in some corners of the market. Instead of shrinking, sales headcount is actually expanding. Researchers from ZS, a global professional services firm, who penned the article, trace where and why that growth is taking place. Their findings reveal something salespeople already feel in their gut: in high-stakes, high-complexity deals, human touch is irreplaceable.

The story begins with complexity. When a customer is buying a commodity like office supplies, standardized hardware, or repeat pharmaceuticals, self-service portals and digital transactions work well. AI makes the process cheaper, faster, and more efficient. But in situations where the offering is ambiguous, novel, or technically demanding like software platforms, advanced manufacturing systems, (even new AI services), buyers need (and want) guidance. They don’t want to add to cart; they need a partner who can help them frame the problem, navigate internal politics, and figure out how to capture value after the ink dries on the contract. In those scenarios, headcount is not declining. It’s going up.

The role of the salesperson, however, is obviously not what it used to be. Just five years ago, a rep might have spent most of their time prospecting and booking meetings. Today, AI is taking on much of the repetitive legwork: researching accounts, identifying warm leads, automating follow-up reminders. That frees human reps to step into a different identity. Not as mere product pushers, but as consultants, orchestrators, and value translators. The best salespeople are becoming diagnosticians who help customers define problems they didn’t know they had.

Of course, not every sector is seeing this kind of growth. Traditional transactional sales in industries where the buyer already knows what they want are shrinking. Self-checkout doesn’t just exist at the grocery store; it exists in B2B procurement portals too. If your value proposition is purely about speed and price, AI and automation will eat into your job. But that’s the point: those roles were already vulnerable because they didn’t require the deeper human skills that complex sales demand.

So what should today’s salesperson take away from this? First, the market is sending a clear signal: double down on skills AI can’t easily replicate. That means negotiation, strategic storytelling, and the ability to make sense of ambiguity. Second, lean into the tools. The teams that are actually growing aren’t afraid of AI. They use it to clear away the low-value tasks that suck time and energy, freeing themselves up for the conversations that matter. AI becomes an assistant, not a competitor.

The risk, of course, is in treating AI as a shiny new toy rather than a strategic shift. Companies can overspend on software without investing in the change management or training needed to make it work. Reps can fall into the trap of letting the machine do all the talking, forgetting that a customer can smell a canned response a mile away. It’s clear that the winners are not the ones who throw the most bots at the funnel, but the ones who design a thoughtful division of labor: humans where judgment, trust, and creativity matter; machines where scale and speed rule.

The bottom line is both sobering and encouraging. If you’re in a role that’s highly transactional, the pressure is only going to increase. But if you’re in a role that requires you to navigate complexity, your value has never been higher. In fact, companies are expanding those teams, precisely because the stakes are so high and the products so complicated.

A workplace book for people who hate workplace books!

I Hope This Email Finds You Never is what happens when someone finally writes about work without the corporate BS.

4.1 stars on Amazon and packed with the real advice you need:

How long you can milk being "new" before someone expects you to actually work
The art of fake apologies that preserve your honor
Strategic camera angles for maximum Zoom intimidation
Kitchen politics and why eating someone's yogurt is literally a crime
Calendar management that includes adequate crying time
Writing your resignation letter when you've been resigned since day one

From Orientation (aka The Descent) to Working Remotely (wink wink) to Coworkers (your fellow inmates), this book covers everything you need to survive the modern workplace.

Warning: This book will not make you successful. But it might keep you sane.

Buy now!

MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

Which commission management platform did Salesforce acquire in 2023?

A. Forma.ai
B. Spiff
C. CaptivateIQ
D. QuotaPath

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).

This was only my second month at my first sales job. One of the older reps had been assigned to take me under his wing. He seemed to genuinely like me and wanted to help me grow. He invited me to come with him to a client lunch. It was low stakes with a long-term client, but I was excited—it was my first ever business lunch—and it felt like I was doing “real business” stuff.

We went to a nice Italian restaurant. I was mostly just quiet while my mentor and the client chatted. I ordered a simple chicken dish. When the food arrived, the client had this incredible looking bolognese pasta. To this day, I still don’t know what possessed me to do this, but as soon as the waiter put his plate down, I blurted out, “Wow, that looks amazing! Can I have a bite?”

The table went silent. The client just stared at me and said, “Uhhh… no.” My mentor gave me a wicked side eye before making a joke and saying I was just kidding. The rest of the meal moved on after an awkward 30 seconds.

My mentor gave me a light dressing down on the car ride back to the office. He wasn’t mad, just surprised/disappointed. But yeah, he never took me to another client lunch.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- September 2025

WORTH A PEEK

If you were a 25-year-old sales rep again (some of you might be now) what would you tell yourself? This question was posed on a recent Reddit thread, with some good advice and occasional funny responses. 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,

Last quarter, my manager started leaning on me to take more of a leadership role. At first it was small stuff like helping onboard a new rep, answering questions in Slack, and sitting in on client calls for training. But it’s since snowballed. Now, the team comes to me with every problem. I’m coaching, I’m troubleshooting, I’m basically the go-to person whenever my manager is tied up.

Here’s the kicker: none of this was discussed with me. It just… happened. I’ve asked about whether there’s a path to promotion, but all I get is vague encouragement like “you’re on the right track,” or “we’ll revisit it next quarter.” In the meantime, my workload has doubled and I’m not making a cent more than I was before.

It feels like I’m in this weird limbo. I’ve been “promoted” in terms of responsibility, but not in title or pay. How do I stop being the unpaid safety net and actually turn this into a real opportunity?

Uneasy in Connecticut

Dear Uneasy,

Taking on a manager’s workload without the title or pay isn’t a promotion—it’s free labor. The upside is that you’ve already proven you can lead. The next step is to make it formal. Document the extra responsibilities you’ve taken on, then have a direct conversation with your manager: “I’ve been doing X, Y, and Z. What’s the timeline and criteria for a promotion with adjusted compensation?” If they can’t give you specifics, it’s a sign you may need to find an organization that will. Good luck!

Quiz Answer: B. Salesforce acquired commission management platform Spiff in 2023 (You can read the source article here).

SHARE THE QUOTA

Help us grow, and we'll send you a reward!

How did you like today's story?

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

Was this email forwarded to you? Sign up here.

Advertise with us

Books

QUOTA MEDIA LLC

651 N. Broad Street., Suite 206
Middletown DELAWARE (DE) 19709
USA

Unsubscribe | Change Subscriber Options