A handshake gone terribly wrong

Published: Wed, 10/29/25

Updated: Tue, 11/04/25

October 29, 2025

TOGETHER WITH

Welcome back to The Quota, the sales newsletter Martha Stewart has said “Would be worth going back to prison for.” In this week’s spooky issue, we’ll take a look at the state of cloud sales in late 2025. Then, we’ll share a Sales Fail about a handshake gone wrong, and give some advice to a rep whose coworker is an insufferable LinkedIn poster. Enjoy!

NUMBER OF THE WEEK

29% of sales pros say that reducing their tech stack would make them more efficient.

Source: HubSpot

SALES ROUNDUP

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

A Kia salesman in Houston is accused of stealing nearly $70K from customers through a dealership scheme. Between Aug. 2024 and Feb. 2025, Emil Conrad Parker allegedly stole a total of $68,700 from 14 victims who believed they were making cash down payments toward vehicles. Instead, investigators said Parker stopped responding to the victims, and no vehicles were ever delivered. You can read more about it here.
Microsoft will exempt many sales roles from its coming return-to-office mandate, offering a more flexible approach than many of its tech industry peers. For some client and partner-facing roles, “we recognize that the nature of work differs from other parts of Microsoft,” human resources executive Theresa McHenry wrote this week in a memo to employees that was reviewed by Bloomberg. The carveout includes roles such as commercial sales and solution engineering. Good stuff! You can read more about it here.

FEATURE

The State of Cloud Sales: Quota Attainment Finally Climbs

After more than two years of stagnation, quota attainment in the cloud sector is finally showing signs of life. According to RepVue’s Q3-2025 Cloud Sales Index, sellers closed the quarter with an average attainment rate of 43.2%—the highest since mid-2023. Inbound lead flow sentiment also ticked up slightly from last quarter’s record low, suggesting early signs of recovery in what has been a tough market.

The RepVue Cloud Sales Index, based on data from 249 companies, 49,000+ quota-carrying professionals, and over 2 million data points, offers one of the clearest pictures of performance trends across the B2B SaaS landscape.

1. Quota Attainment Trends Higher

Quota attainment inched upward this quarter to 43.24%, paired with a lead flow sentiment of 2.73. That’s still below pre-2022 highs, but it’s progress nonetheless. The uptick was led by strong performance in the Data & AI sector, which continues to drive overall improvement. RepVue notes that cybersecurity, the largest sub-vertical by sample size, remains a drag on the broader index, with both quota attainment and lead flow sentiment trailing other categories.

2. Data & AI Keeps Momentum

The Data & AI and Sales Tools sub-verticals led the way, posting year-over-year quota attainment gains of 7% or more. Sales Tools also posted the highest lead flow sentiment (2.9), supported by strength across companies like Salesforce, the largest single component of the Index.
Other segments, Finance & ERP, Marketing Tools, and HR Tools, saw moderate improvement, while DevOps & Developer Tools slipped slightly, weighed down by weaker marks from Atlassian and Splunk. HR Tools, meanwhile, surpassed 45% attainment, largely on the strength of privately held vendors outperforming their public peers.

3. Bigger Deals Drive Results

Every deal size bucket saw improvement year-over-year. The largest deals, $200K+ ACV, continue to dominate, with 48.3% of reps hitting or exceeding quota. Even smaller deal tiers showed gains, though sub-$50K ACV segments lagged behind the Cloud Index average.

In a market where cycles are lengthening, the rise in deal size likely helped offset slower close rates. As RepVue puts it: bigger deals help you get to quota faster.

4. Sales Cycles Get Longer

Across the board, sales cycles extended this quarter. That applied to every deal size, from SMB through enterprise. It’s a clear signal that while demand is returning, buyers remain cautious and complex deals take longer to close.
The report notes that the improvement in attainment, despite this lengthening, is particularly encouraging given the “time kills deals” reality of B2B selling.

5. Key Accounts Hit Record Highs

RepVue’s Key Accounts and Mid-Market segments both reached new highs in average contract value. Key Accounts broke through the $300K mark for the first time, landing at $324K—a 20% year-over-year increase. Mid-Market deals also rose 16% to $67K. Enterprise and SMB deal sizes remained steady. These larger contract values likely contributed to the overall quota gains, cushioning sellers against slower sales cycles.

The Big Picture

For the first time in nearly two years, the cloud sales environment looks slightly less bleak. Gains are broadening, led by Data & AI and Sales Tools, with Key Accounts showing strong deal economics. Cybersecurity remains a drag, but momentum is returning in key growth sectors.

RepVue’s index continues to show that macro recovery in sales performance is uneven, but the direction is finally upward. Sustained progress over the next few quarters will determine whether this is a true turnaround—or just a blip in a still-challenging SaaS landscape.

Source: RepVue Cloud Sales Index – Q3 2025

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MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

What was the name of the Toms River, NJ insurance salesman convicted of hiring hitmen to kill his wife in 1984?

A. Robert Marshall
B. Paul Langtham
C. Charles Rivier
D. Robert Durst

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 marketing software to small businesses and had been courting this boutique agency owner for two months. She finally agreed to meet at a coffee shop downtown to talk details.

The meeting went great. She loved the demo, asked all the right questions, and even mentioned her budget unprompted. I was feeling confident.

When we finished, I stood up and extended my hand across the table for a closing handshake. At the exact same moment, she reached down to grab her purse from under her chair.

My hand just hung there in the air while she bent down. I froze, not knowing whether to hold it there or pull back. She swung back up so quickly I didn’t have time to react, and my hand ended up hitting her in the face.

She let out an audible “oh!” and I ripped my hand back and started apologizing.

She laughed nervously while rubbing her head and said it was fine and that we’d follow up for next steps over email. She signed with us two weeks later and is still a customer, but every time we’re on a call, I think about that moment and shudder.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- October 2025

WORTH A PEEK

What do you do when a prospect doesn’t express much pain about their current situation? Dig deeper? Create some? This question was posted to Reddit, and answers were quite helpful. 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 work in B2B software sales, and there’s a guy on my team who is just unbelievably annoying on LinkedIn. Every time he books a meeting or closes a deal, it’s a full-blown post with hashtags, emojis, and a 400-word “lesson” about perseverance. He even tags clients, including mine, and occasionally exaggerates shared deals to make himself look like a top performer.

The kicker? He’s not even in the top three reps. It’s just constant humblebragging and secondhand embarrassment. I know I shouldn’t care, but it’s driving me insane. How do I handle this without looking jealous or petty?

Scrolling in New York

Dear Scrolling,

Every office has one: the self-appointed LinkedIn thought leader. The truth is, you gain nothing by engaging. Scroll past, mute his posts, and let the algorithm handle the rest. Focus on your pipeline, not his personal brand.

That said, it’s fair to draw the line if he’s tagging your clients or claiming shared wins. Just have a quick, polite chat and ask him to leave your accounts out of his posts, then move on.

Quiz Answer: A. Robert Marshall was the name of the Toms River, NJ salesman convicted of hiring hitmen to kill his wife in 1984 (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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