When a prospect overhears you hyping yourself up

Published: Wed, 03/12/25

Updated: Fri, 03/14/25

March 12, 2025

TOGETHER WITH

Welcome back to the first post-Daylight Savings Time issue of The Quota—as if you needed another way to screw up your circadian rhythm. In this week’s newsletter, we’ll take a look at how pop culture has shaped the public's perception of salespeople over the years, share a Sales Fail about affirmations, and give some advice to a rep who’s been assigned an additional role. Enjoy!

NUMBER OF THE WEEK

193

Over 193 million business emails are estimated to be sent and received daily.

Source: Sopro

SALES ROUNDUP

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

Meeting a salesman at a Georgia furniture store turned out to be a lifesaving moment for a woman who would soon need a kidney donor. Dayna Cohen was in the market for a chair when she met salesman Jake Rowland at a Rooms to Go furniture store in Savannah, Georgia. Six months later, Cohen’s health took a turn for the worse, and she was told her kidneys were failing—she needed a transplant. The salesman got tested, and found he was a perfect match. You can read more about what happened here.
A San Francisco man has accused a car salesman of launching a harassment campaign against him after an awkward encounter at a dealership. The customer, who was looking to buy a Lexus, said that after he left a Lexus store without buying a car, the salesman allegedly began calling and texting him relentlessly. After he cursed at the salesman and told him to leave him alone, he says he was inundated with calls from other dealerships, and from people responding to a fake job posting. You can read the full story here.

FEATURE

Image: Ed Yourdon licensed CC BY-NC-SA 2.0

Willy Loman to Wolf of Wall Street: How pop culture shaped the public's perception of salespeople

For decades, our collective understanding of salespeople has been shaped by their portrayal in popular culture. These fictional characters have not only reflected societal attitudes but actively molded them, creating impressions that real sales professionals still contend with today. Let’s explore the different creative works that have featured salespeople and how they were portrayed.

The Tragic Salesmen

Death of a Salesman (1949)

Arthur Miller's Pulitzer Prize-winning play, later adapted for film and television, gave us Willy Loman, the quintessential failed salesman. Loman embodies the fading salesman whose career is built on being "well-liked" rather than creating value. As his charm diminishes, so does his ability to sell, leading to financial ruin and personal tragedy. The play cemented the image of the traveling salesman as a tragic figure clinging to an outdated version of the American Dream, ensuring generations form their first impression of sales through Loman's downfall.

Glengarry Glen Ross (1984, 1992, 2025)

David Mamet's Pulitzer-winning play and subsequent film portrays desperate real estate salesmen in a cutthroat competition where only top performers keep their jobs. The film's iconic "Always Be Closing" speech (added to the movie script as a favor to Baldwin) introduced phrases like "coffee is for closers," depicting salespeople as both morally compromised and victims of a brutal corporate system. This portrayal continues to influence how companies structure sales incentives, serving as both warning and motivation for sales teams. The play just re-opened on Broadway starring Kieran Culkin, Bob Odenkirk, and Bill Burr.

The Slick Operators

Wall Street (1987)

Oliver Stone's Academy Award-winning film presents Gordon Gekko, who frames financial sales as a predatory profession where the goal is selling clients on deals primarily benefiting the salesperson. Gekko's "Greed is good" speech reframed selfishness as a virtue. Many viewers and professionals admired rather than condemned him, with the film inadvertently creating a template many ambitious salespeople aspired to follow.

The Wolf of Wall Street (2013)

Martin Scorsese's adaptation of Jordan Belfort's memoir received five Oscar nominations and presents stockbrokers as manipulative hustlers selling worthless stocks to unsuspecting clients. While technically cautionary, the film's energetic portrayal made the profession seem simultaneously reprehensible and alluring. Sales training seminars saw increased interest afterward, with many wanting to learn Belfort's "Straight Line" selling system despite its ethical problems.

The Redemptive Narratives

The Pursuit of Happyness (2006)

Gabriele Muccino's film, earning Will Smith Oscar and Golden Globe nominations, shows sales as a pathway to economic mobility. Chris Gardner demonstrates persistence and product knowledge as keys to success rather than manipulation. The film provided a humanizing counterpoint to negative stereotypes, depicting cold calling and relationship building as legitimate skills requiring discipline and perseverance.

Jerry Maguire (1996)

Cameron Crowe's Oscar-nominated film portrays sports agencies as torn between relationship-based and transactional approaches. The protagonist rejects volume-based client acquisition for exceptional service to fewer clients. While popularizing "Show me the money!", it actually tells a story about rejecting purely profit-driven sales approaches, helping popularize consultative selling and quality over quantity in client relationships.

Television's Evolving Portrayals

Mad Men (2007-2015)

Matthew Weiner's Emmy-winning AMC series depicted advertising executives as creative artists who function as salespeople. The show romanticized the profession while simultaneously critiquing its ethical compromises, portraying sales as a sophisticated psychological game requiring deep understanding of human desires rather than purely transactional work.

The Office (2005-2013)

Greg Daniels' adaptation of the British series became an American comedy cornerstone that presented paper salespeople as a mix of competent professionals (Jim), overeager rule-followers (Dwight), and delusional managers (Michael). By focusing on office relationships and personal quirks, the show made sales seem relatable and ordinary rather than glamorous or predatory.

Modern Evolution

Silicon Valley (2014-2019)

Mike Judge's Emmy-winning HBO satire depicted enterprise tech sales as requiring both technical knowledge and political savvy, with plenty of absurdity in between. It highlighted the tension between product-focused founders and sales-oriented executives, capturing the shift toward solution selling in complex B2B environments while updating popular understanding of what modern sales looks like in technology sectors.

These cultural representations matter — they shape how customers approach sales interactions, how organizations structure sales roles, and how individuals perceive their own sales careers. The evolution from Willy Loman's desperate glad-handing to the complex strategic selling of modern portrayals reflects real changes in the profession itself. It’s important to recognize these perceptions, address them honestly when they surface, and ultimately demonstrate that effective modern selling isn't about manipulation or desperation—it's about creating genuine value.

HOW TO ACTUALLY BRING AI INTO YOUR SALES WORKFLOW

Efficiency is everything. Agent.ai helps outbound sales teams combine social insights and CRM data so you can spot new opportunities and convert faster.

With AI-driven agents that integrate seamlessly with HubSpot, LinkedIn, and other data sources, you don’t need to reinvent your workflow—just find the few agents that work best for you.

Agent.ai makes it easy to:

✅ Find the right prospects – Use AI to pull LinkedIn data, track engagement, and identify decision-makers.

✅ Automate research – AI agents can monitor company news, competitor activity, and social signals so you’re always in the loop.

✅ Save time on follow-ups – Research contacts and keep track of social updates so you can make the best approach when breaking the ice.

Working Together: Sales teams + AI Agents

🔹 LinkedIn Profile & Activity Trackers – Get notified when a prospect engages with content or changes roles.

🔹 HubSpot CRM Triggers – Use or build an agent that is triggered by actions in HubSpot or other Agent.ai partners.

🔹 Competitor Research & Sales Intel Agents – Stay informed about shifts in your prospects’ industries or social mentions of your competitors.

🔹 Email Subject Line & Message Generators – Get AI-driven suggestions based on past response rates.

Free access, free AI agents and the option to build your own (also free), Agent.ai makes sales automation flexible and practical.

Explore how social data plus CRM insights can accelerate your pipeline at Agent.ai!

Try for free!

MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

How many total employees does Salesforce have in 2025?

A. 112,489
B. 121,019
C. 588
D. 76,453

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).

A few years ago, I arrived at a prospect's office. It was the first in-person meeting, but we had a handful of good calls and I was looking to close the deal. I asked the admin who was showing me around where the bathroom was. I went inside and started to whisper some positive affirmations to myself in the mirror. It sounds silly, but they really do help me. I kept repeating, "You're a professional, and you're going to close this deal."

After about a minute, I heard a toilet flush and a guy walked out and started washing his hands next to me. I wasn't sure if he had heard me until he looked at me with a smile and said, "Good luck," before walking out. I was super embarrassed but decided I wouldn't let it throw me off my game. This was until I walked into the meeting and saw the guy sitting there.

It turned out he was the general counsel for the company. I was shaken at first, but he didn't say anything. He just smirked at me and gave me an approving head nod. I don't know why, but it seemed like he was rooting for me. I'm guessing he must have been in sales at some point in his career. I went ahead with my pitch. I didn't close them that day but got the signature two weeks later. Now I do my affirmations in the car.

Anonymous Location withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- March 2025

WORTH A PEEK

Is it possible to make $150k+ per year in sales and still have time to enjoy life and travel? This was a question recently posted to Reddit, which garnered 254 responses, ranging from software, to medical device, to “no.” 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,

I'm a sales rep for a marketing agency and I'm drowning. Last month, our company restructured and eliminated our account management team "to streamline client communication." Now, after closing deals, I'm suddenly responsible for managing the entire execution process—coordinating with our creative team, tracking deliverables, presenting results, and fielding all client complaints. I'm spending more time putting out fires for existing clients than prospecting for new ones, and my pipeline is suffering. They have raised my base compensation and added extra retention incentives, so I'm being compensated for the extra work, but this isn't what I signed up for. I enjoy being an individual contributor. I just want to sell, I don't want to be a project manager. How do I convince leadership that this model isn't working without sounding like I'm not a team player?

Overworked in Location Withheld

Dear Overworked,

You're being set up to fail. Sales and account management require fundamentally different skills, time management approaches, and compensation structures—and there's a reason why they're traditionally separate positions. Start by documenting exactly how your time is being allocated. The most compelling argument will be the numbers—when they see the direct impact on the company's bottom line, they'll be more likely to reconsider. Track one full week, noting every hour spent on account management versus sales activities. Calculate the opportunity cost: "I spent X hours on account management, which based on my close rate and average deal size equals approximately $Y in lost revenue for the company." Request a meeting with leadership and frame your concern in terms of company growth, not personal preference. Good luck!