The sales manager who only talks about himself

Published: Wed, 03/04/26

Updated: Fri, 03/06/26

March 4, 2026

TOGETHER WITH

Welcome back The Quota, the sales newsletter to end all sales newsletters (yes, this is a threat). In this week’s issue, we’ll look at how sales reps can make themselves AI-proof in our brave new world. Then, we’ll share advice, Fails, memes, and more. Relax, enjoy, and don’t think too hard—it will all be okay!

NUMBER OF THE WEEK

50 percent of companies don’t respond to prospect inquiries until five business days later.

Source: Zendesk

SALES ROUNDUP

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

Sales reps at $11 billion AI startup ElevenLabs have to bring in 20 times their base salary, or they're out, the VP says. Speaking on the 20VC podcast on Friday, Carles Reina, VP of sales at the voice-cloning startup, talked through its "ruthless" quotas. "So if I pay you $100,000 a year, your quota is $2 million. That's it. If you don't achieve your quota, then you're going to be out, right?" Reina said. "And we're ruthless on that end." ElevenLabs, which was recently valued at $11 billion after closing a $500 million funding round, operates in micro-teams of five to ten people each, according to CEO and cofounder Mati Staniszewski. You can read more about it here.
Salesforce has signed an agreement to acquire San Francisco-based startup Momentum to boost the capabilities of Agentforce 360 and Slack for enterprise sales teams. The acquisition will allow Salesforce to extend Agentforce 360 and Slackbot’s ability to ingest and analyze unstructured data from third-party voice and video channels, such as Zoom and Google Meet, and apply those insights directly to agentic workflows so that sales teams can be armed with actionable revenue insights, the company said in a statement. You can read more about it here.

FEATURE

The 5 Skills That Will Keep Your Sales Job Secure in the Age of AI

If the last few months have felt different, you’re not imagining it.

Between the mass adoption of tools like Claude Code and a wave of AI copilots flooding CRMs, inboxes, and sales workflows, the conversation has shifted. What started as “this might help with admin work” quickly turned into “wait… can this thing run discovery calls?”

Every sales Slack group now has at least one doomsday thread:

• SDRs will be replaced by AI agents
• Auto-personalized outbound at scale
• AI-generated proposals in seconds
• Chatbots qualifying leads better than junior reps

It’s enough to make anyone wonder how secure their seat really is.

But here’s the reality: the mechanics of selling are getting automated. Which means the human edge is getting more valuable. If you want to stay relevant—and indispensable—these five skills matter more than ever.

1. Business Acumen (The Real Kind)

AI can summarize a 10-K. It can scrape a LinkedIn profile. It can even suggest “pain points.” What it can’t do well is synthesize messy, ambiguous business context in real time and connect it to a buyer’s internal politics. Reps who survive this shift understand:

• How their customer actually makes money
• What pressures leadership is under
• Where risk lives inside the org
• How decisions really get approved

The rep who can say, “Here’s how this affects your Q3 margin target,” will always outrun the rep who reads from a generated script.

2. Emotional Intelligence Under Pressure

AI can draft empathetic language. What it can’t do is read the micro-hesitation in someone’s voice when budget comes up. Great reps pick up on:

• Tone shifts
• Unspoken objections
• Political tension in group calls
• When someone is posturing versus genuinely concerned

As buying committees get larger and more complex, emotional navigation becomes a differentiator. Deals fall apart because of people dynamics far more often than because of missing features.

3. Problem Framing

Anyone can present a solution. Fewer can define the problem in a way that makes action feel urgent. AI can answer questions. But top reps can reshape the question. When you can say:

• “The real issue here isn’t onboarding time, it’s churn risk in month three.”
• “You don’t have a tooling problem. You have a prioritization problem.”

You become a thinking partner rather than a vendor. That role does not get automated easily.

4. Narrative Control

Buyers are overwhelmed with information. AI just adds more. The reps who win will be the ones who:

• Tell a clean story
• Simplify complexity
• Connect dots across departments
• Give buyers language to sell internally

Every deal needs a champion. Champions need a narrative. If you can equip someone with a clear, repeatable story they can carry into a boardroom, you’re not replaceable.

5. Leverage of AI (Instead of Fear of It)

For better or worse, the safest reps in the age of AI are the ones using it.
Use AI to:

• Prep for calls faster
• Draft follow-ups with precision
• Analyze deal notes
• Simulate objections
• Refine messaging

Reps who treat AI like a threat will move slower than the reps who treat it like a power tool. The future sales org will have fewer reps who each operate at a higher level. The winners will be those who combine judgment with automation.

AI will eliminate busywork. It will standardize mediocre outreach. It will flatten average performance.

But what it won’t do well is build trust in uncertain environments, manage egos, read rooms, and frame decisions that feel risky.

The job is evolving. The bar is rising. But the opportunity is still there. And if you build these five skills, your seat at the table looks a lot more secure than the headlines would suggest.

TOGETHER WITH I HOPE THIS EMAIL FINDS YOU NEVER

I Hope This Email Finds You Never is what you get 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

How much does the average car salesperson make per year?

A. $83k
B. $61k
C. $101k
D. $94k

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 was once on a popular reality show at the same time I worked for a small company with a boisterous owner/president.

We had staff meetings on Thursday mornings and this included in-office and remote staff. The remote reps started coming onto the call and started mentioning my appearance on the reality show the night before. We were discussing how it went, what meeting the stars was like, etc. Usually, I didn’t talk this much because the owner was usually busy with all his stories and training tips at the start of meetings. However, that day, he was a few minutes late.

Eventually, he came into the room for the meeting, and we are still discussing the TV appearance. Naturally, the owner assumed we were talking about him. So he injected himself into the conversation, referring to some news story about earthquakes and fracking in Pennsylvania and how he gave his opinion on that.

Finally, he stopped talking. Everyone was staring at him, wondering what he was talking about. Then, one remote rep said, “No, we saw him (me) on tv last night on that reality show.” The owner’s jaw hit the floor. I don’t know if it was because he couldn’t believe I was on the show or that the discussion was, for once, not about him!

Anonymous

GRAPH OF THE WEEK

Source: LinkedIn Poll -- March 2026

WORTH A PEEK

Want to read about one of the worst sales job interviews of all time? A recent post on Reddit by a rep who interviewed with a tech founder was a doozy—and the comments were fun to read too. 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’m in my third year out of college working as an SDR. I make decent money for my age, and I’m (likely) on track for a promotion into an AE role. For the first time in my life, I’m not stressed about money.

The problem is: I don’t actually want to be in sales.

Since high school, I’ve wanted to be a travel photographer. I shoot on weekends regularly. A few of my photos have been picked up by small blogs and digital brands. Every time I’m on a plane or somewhere new with my camera, I feel more alive than anywhere else.

But I also know how this story can go. I quit, travel for six months, burn through my savings, and end up back in sales — just older and more broke.

My friends tell me to “follow my passion.” My parents tell me to “do what feels right.” I feel stuck in between. Do I stay the course and build financial security first? Or do I take the leap while I’m young? Who knows what could happen in the meantime. Tomorrow is never promised.

Longing in Location Withheld

----

Dear Longing,

Right now, photography feels pure because it carries no pressure. Sales feels heavy because it pays your bills. The second photography becomes your sole source of income, it will inherit some of the stress you’re trying to escape.

Before you make any leap, treat photography like a business. Can you consistently generate revenue from it? Not just likes or compliments. Revenue. Can you land paying clients while still employed? Can you build a portfolio? Can you save 12 months of living expenses, not six.

Remember this: sales is not your prison. It’s your investor. It can fund your dreams. Use it strategically. Build skills, build your savings, and build discipline. Set a concrete runway: maybe a dollar amount, or a client count. When you hit those benchmarks, reassess. Work toward your dreams, but don’t do it blindly. Make decisions the future you will be thankful for.

Quiz Answer: A. The average car salesperson makes $83k per year (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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