The lost art of the "relationship rep"

Published: Wed, 01/21/26

Updated: Sat, 01/24/26

January 21, 2026

TOGETHER WITH

Welcome back to The Quota, where your daily dose of sales juice is concentrated in a vial, then cooked at 400 degrees and delivered weekly. In this week’s issue, we’ll look at the death of the relationship rep, share a Sales Fail about messy eating, and give the usual advice to the usual suspects. Sit back and enjoy!

NUMBER OF THE WEEK

45% of high-performing sales teams have already adopted hybrid human-AI SDR models.

Source: Outreach

SALES ROUNDUP

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

Microsoft stock fell 2% last week after The Information reported sales teams missed AI growth goals. Azure Foundry product— Microsoft's enterprise AI platform—saw widespread sales shortfalls across multiple teams. Quota reductions are rare for Microsoft, suggesting deeper challenges in enterprise AI adoption than previously known. The miss comes as Microsoft positions AI as its primary growth driver heading into 2025. You can read more about it here.
Shipping giant UPS has rolled out a new structure for its U.S. sales team, resulting in layoffs and instances of friction for some customers, consultants told Supply Chain Dive. The changes resulted in two distinct sales roles: Business development managers that focus on securing new sales, and customer success managers that emphasize retaining and growing existing business. UPS added that “a small number of employees were impacted” by the organizational adjustment but did not provide an exact figure. You can read more about it here.

FEATURE

"handshake" by recombiner is licensed under CC BY-NC-SA 2.0.

The Lost Art of the Relationship Rep

In the mid-1970s, a sales rep covering northern Ohio could reasonably expect to retire with the same customers he started with. He knew which buyers hated surprises, which ones always waited until the last week of the quarter, and which assistant actually decided what made it onto the calendar. When something went wrong, he drove out and sat in the office until it didn’t feel awkward anymore.

That rep didn’t think of himself as a “relationship seller.” He was just doing the job. Today, that job barely exists.

When Sales Was Slow Enough to Remember Names

For much of the twentieth century, selling rewarded patience. Companies sold physical products, signed multi-year contracts, and measured success in long arcs. Customers stayed put. Vendors stayed put. The rep in between became part of the furniture.

At firms like IBM and Xerox, field reps were expected to stay with accounts for years. Sometimes decades. Promotions came from consistency, not velocity. A rep’s value lived in memory: who preferred phone calls, who hated contract language, who needed to be buttered up before feeling sold—think the account managers in Mad Men. In that world, the relationship wasn’t a nice-to-have. It was the product.

Scale Starts Asking Uncomfortable Questions

The first real pressure on the relationship rep came from inside. As companies expanded, leadership wanted visibility. Forecasts. Predictability. Fewer surprises tied to personalities. Reps who “just knew” their customers made executives nervous. Knowledge locked inside people felt risky.

So systems arrived. First as spreadsheets. Then as databases. Then as full CRMs. Once customer history could be logged, reviewed, and transferred, account ownership became flexible. Territories could be redrawn. Coverage could be optimized. The rep stopped being the archive. That shift fundamentally changed the job.

Speed Replaces Stewardship

Software accelerated everything. Products updated constantly. Buying cycles shortened. Growth targets became aggressive. Public markets rewarded momentum instead of slow and steady (healthy) growth. In that environment, long-term account ownership started to look inefficient.

Specialization followed. New business reps hunted for logos. Account managers handled renewals. Customer success teams focused on adoption. Expansion became its own motion. The single rep who once handled everything from introduction to renewal turned into a relay runner passing the baton every few quarters.

Each handoff made sense on paper… but every handoff thinned the relationship. Customers met more sellers. Sellers spent less time with each account. Familiarity faded.

Measurement Quietly Wins the Argument

Modern sales organizations didn’t reject relationships. They simply stopped rewarding them. Territories changed. Compensation favored new bookings. Staying with the same account year after year rarely helped a rep’s upside. Moving on usually did.

Meanwhile, the artifacts of relationship stayed behind. Notes in the CRM. Account plans. Call summaries. Quarterly business reviews. The appearance of continuity survived, even as the people rotated.

Reps learned the rules quickly. Build rapport, but don’t linger. Know the account, but don’t get attached.

What Actually Disappeared

The loss wasn’t charm or care. Plenty of modern reps are thoughtful and invested. What disappeared was time. Time to watch a customer grow. Time to sit through a bad quarter without panic. Time to be trusted before being measured.

The relationship rep thrived in a slower economy with fewer tools and fewer expectations. Today’s economy prizes speed, coverage, and predictability. Trust still matters, but it’s expected to form faster and travel further than it ever did before.

A Fair Trade, With Consequences

It would be easy to romanticize the past, but the old model had real problems. Reps hoarded information. Managers flew blind. Customers were exposed when their rep left. Modern systems fixed those issues. They made selling more reliable. They reduced dependence on individuals. They made growth possible at levels the relationship era couldn’t support.

But the fix came with a cost. Selling became thinner. Faster. Less personal. Customers learned to expect turnover. Reps learned not to promise permanence.

Where That Leaves Us

Companies still talk about long-term relationships. They just pursue them through systems instead of tenure. Trust has been spread across teams, tools, and processes. More resilient, maybe. Less human, absolutely.

The relationship rep didn’t disappear because the role stopped working. It disappeared because the world around it sped up, and asked the seller to behave more like a machine. Somewhere along the way, remembering names became optional.

The Buyer Enablement Playbook

Top reps don’t “sell.” They create the conditions to buy.

Get the exact frameworks, templates, and real deal examples from AEs at Gong + Deel to build champions, multithread faster, and keep deals moving between calls.

Get the playbook!

MEME OF THE WEEK

Source: Monday CRM

QUIZ

How long does the average sales rep stay at a job?

A. 18 months
B. 4 months
C. 26 months
D. 22 months

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 mid-deal with a prospect who ran a manufacturing plant (I sell logistics software). I’d been working on the deal for a couple of months, and the guy finally agreed to meet in person to talk details over lunch. He picked the place. Barbecue. I didn’t think twice about it. I was just happy to be out of email and into the real world.

He knew everyone that worked there. He was a regular and took the lead on ordering. He ordered ribs. A full rack and some sides.

That’s when I remembered something important about myself: I’m a notoriously messy eater. I like to be clean. I over-napkin. I’m the guy who uses ten napkins for a sandwich. But it was too late. The food was already on the table.

I tried to pace myself, but the sauce was everywhere. Fingers, plate, table. I kept reaching for napkins on instinct. By the halfway point, I had built a small, greasy pile beside my tray. Somehow this guy, apparently a professional rib-eater, had barely made a mess.

The server came by to ask if we needed anything else, and the prospect looked at the napkins, smiled, and said, “Can you bring my friend a wet nap, and maybe a bib” and started cracking up. I laughed along, but was super embarrassed. He was nice about it after and didn’t bring it up again.

I ended up closing the deal, but learned a valuable lesson about making sure to be conscious about what I order when taking prospects out to eat.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- January 2026

WORTH A PEEK

Is it difficult to have kids while working in sales? A recent Redditor asked the audience how they found the time to raise children while working six or even seven days a week. Some responses were sympathetic, while others couldn’t relate. You can see 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 an enterprise AE at a public SaaS company selling security software to Fortune 1000 accounts. I’ve been interviewing quietly because I’m burned out and honestly don’t see a long-term future here.

The problem is I’m mid-deal on the largest opportunity of my career. It’s an eight-figure, multi-year contract that I’ve been working on for almost a year. Procurement is engaged, legal redlines are flying, and if it closes, it would blow out my number and my commission.

Part of me feels irresponsible even thinking about leaving before this is done. Another part feels trapped — like I’m staying for a deal, not the job.

Is it stupid to walk away now, or am I already wearing golden handcuffs?

Impatient in Location Withheld

Dear Impatient,

Opportunities like this don’t come around often, and walking away mid-flight is one of the few career moves you can’t undo. Even if you land somewhere better, it could take a year or two to build the relationships, trust, and pipeline needed to see a deal of this magnitude again.

Close it. Collect the commission. Then reassess with leverage, clarity, and options.

Quiz Answer: A. The average tenure of a sales rep is 18 months (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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