Why selling against an incumbent is so hard

Published: Wed, 02/04/26

Updated: Wed, 02/04/26

February 4, 2026

TOGETHER WITH

Good morning Quota readers. Have you been staying warm? What’s the temperature like where you live? What’s your favorite color? In this week’s issue, we’ll look at why selling against an incumbent product can be so difficult. Then, Sales Fails, advice, and more. Let’s go!

NUMBER OF THE WEEK

Sales reps can spend up to 40% of their time searching for someone to call

Source: Inside Sales

SALES ROUNDUP

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

A car salesman in Windsor, Ontario has been charged with defrauding 15 people out of a total of $40,000, according to city police. Authorities say the alleged offences took place between January and September of 2025. Police accuse the 32-year-old of selling multiple vehicles under false pretenses. “Investigators determined that some vehicles had odometers rolled back, others were sold with fraudulent safety inspections, some buyers never received the vehicles they purchased, and others unknowingly purchased scrap vehicles that had been misrepresented as roadworthy,” the Windsor Police Service said. You can read more about it here.
A Wyoming man who pulled a gun on a door-to-door salesman that he believed was harassing his wife was sentenced to probation. Last Tuesday, District Judge Stuart S. Healy III sentenced Robert S. Peters, 61, to two and a half to three years in prison, suspended for two years of supervised probation, for aggravated assault, which Peters pleaded guilty to at the end of 2025. Deputy County Attorney Kyle Ferris said that while the “allegations are egregious,” Peters has been a model citizen and has a very limited criminal history, and that he sees no reason why Peters won’t be “a stellar person under probation.” You can read more about it here.

FEATURE

"Switches" by Amaury Henderick is licensed under CC BY-NC-ND 2.0.

The Incumbent Advantage: Why selling against “what they already use” is the hardest job in sales

The challenger had the better product. Everyone in the room agreed. It was faster, cheaper, and easier to use. The demo landed. The spreadsheet comparison favored the new vendor. The buying team nodded through the final meeting.

Then the decision came back.

They were sticking with what they already had.

This outcome plays out every day across industries. Enterprise software. Manufacturing equipment. Medical devices. The pattern is so common that sellers treat it as background noise. A deal lost to “the incumbent” barely counts as a real loss.

What most people miss is that this outcome is not bad luck or weak selling. It is the default behavior of the human brain.

Why What We Already Use Feels Better Than What We Could Have

Behavioral economists call this the endowment effect. People assign more value to things they already own than to identical or even superior alternatives.

The phenomenon was first demonstrated by Richard Thaler in the 1980s and has been replicated dozens of times since. In one classic experiment, participants given a coffee mug demanded roughly twice as much money to give it up as they were willing to pay to acquire it in the first place.

Ownership changes perception. Once something is “ours,” giving it up feels like loss. Acquiring something new feels optional. That imbalance shows up everywhere selling happens.

The Same Story, Different Industries

In enterprise software, buyers complain openly about the tools they use. CRMs are clunky. Analytics dashboards are confusing. Internal workflows are inefficient. Yet when it comes time to switch, discomfort suddenly feels safer than change.

Data from Gartner shows that CRM replacement cycles often stretch beyond ten years, even when satisfaction scores are low. Migration risk outweighs performance gains.

In manufacturing, supplier loyalty persists long after pricing stops making sense. A plant manager may acknowledge that a new supplier offers better margins, but downtime risk carries more weight than savings. The existing vendor already fits into production rhythms. That familiarity protects them.

In medical sales, the bias runs even deeper. Studies on device adoption show that surgeons strongly prefer tools they trained on early in their careers. Switching requires retraining muscle memory, not just reviewing spec sheets. Outcomes matter, but comfort matters more.

Even car buyers fall into the same trap. Research from the National Bureau of Economic Research shows that consumers systematically undervalue trade-in options relative to keeping their current vehicle, even when the numbers favor switching.

What Buyers Are Really Protecting

From the outside, staying with the incumbent looks irrational. From the inside, it feels prudent. Switching vendors means owning the consequences. If the new solution fails, the buyer who pushed for it carries that risk. If the old solution limps along, responsibility diffuses. Everyone already agreed to it once.

There is also identity at play. Changing vendors can feel like admitting the previous decision was wrong. For people whose careers are built on judgment, that admission carries emotional weight. Staying put protects reputation. Switching creates exposure. That tradeoff favors incumbents every time.

The Challenger’s Tax

This is where selling gets unfair. Challengers are not competing against feature sets. They are competing against ownership. Research on loss aversion shows that people require gains roughly twice as large to offset perceived losses.

Translated into sales reality, this means being slightly better does not matter. Being moderately better does not matter. Challengers must be overwhelmingly better to overcome emotional resistance. That requirement explains why modern go-to-market motions look the way they do.

Free trials exist because claims are not enough. Pilots exist because risk must be contained. Proofs of value exist because spreadsheets do not change feelings. Phased rollouts exist because buyers want escape hatches.

In manufacturing, challengers offer guarantees and staggered implementation. In medical sales, peer validation and published outcomes matter more than demos. In software, freemium and land-and-expand strategies reduce perceived loss by postponing commitment.

Why This Never Feels Fair to Sellers

From a seller’s perspective, losing to the incumbent feels like losing to inertia. Effort does not map cleanly to outcome. Skill does not guarantee displacement. That frustration is real. It is also predictable.

Markets move slower than innovation because humans protect what they already have. Sellers who understand this stop treating incumbent losses as personal failures. They start seeing them as the baseline condition of selling.

Winning against an incumbent is not normal. It is exceptional.

Meet Jon Osting - The B2B Whale Hunter

Meet Jon Osting, Founder of Startup Sales Shop. Think of him as the B2B whale hunter who augments your sales team.

Instead of adding headcount and waiting months for reps to ramp, he plugs in immediately to drive pipeline and close bigger deals.

His team's recent catches:
• $15k spend → $125k ARR (8.3x ROI)
• $6k spend → $52k ARR (8.7x ROI)
• $6.5k spend → $24k ARR (3.7x ROI)

No ramp time. No long-term risk. Just experienced sales execution that turns targeted outreach into real revenue.

Worth giving him a call? Book one here:

Book a free discovery call with Jon

You can also connect with Jon on LinkedIn here.

MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

How old was David Mamet when he wrote Glengarry Glen Ross?

A. 42
B. 36
C. 81
D. 28

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).

It was the first onsite with a small professional services firm. Nothing fancy. Just a quick visit after a few decent calls to talk through next steps. We did the handshake, grabbed coffees, and sat down in a little conference room off the main office.

I leaned back in the chair for maybe half a second. Not even fully. Just enough. The chair gave out immediately. One leg snapped and I went straight down. No slow motion. No warning. Papers on the floor. Coffee everywhere.

My prospect jumped up apologizing, saying the chair was old, that it had happened before. I laughed because I was embarrassed and didn't know what else to do. We reset with another chair and tried to keep going.

But the meeting never really came back. Everyone was polite, but rushed. We wrapped early. A week later I got the email saying they were going in a different direction. I don’t think the chair killed the deal on its own. But it definitely didn’t help.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- February 2026

WORTH A PEEK

Last week, we asked the Sales Humor audience whether sales gives you more freedom. Responses overwhelmingly (70%) pointed to yes. A Reddit user posed the same question to the r/sales audience—with more nuanced responses that delve into the why (or why not). 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 a mid-market AE at a Series C SaaS company. My manager has started pushing me to “be more optimistic” in forecast reviews. He wants me to flag deals as upside, pull close dates forward, and assume best-case scenarios that aren’t actually agreed to by the buyer.

The message is pretty clear: leadership wants the forecast to look stronger heading into board meetings. When I push back, I’m told forecasting is about confidence and storytelling, not precision.

I don’t want to be labeled negative or uncoachable, but I also don’t want to train myself to lie. Is this just how forecasting works at this level?

Unsure in Location Withheld

Dear Unsure

Forecasting is supposed to be a tool for making decisions. When forecasts get inflated to look good upstream, they stop helping anyone, and reps end up taking the blame when reality shows up.

It's not necessarily lying, since many businesses give "optimistic projections." But be careful which habits you normalize. Inflated forecasts have a way of becoming empty promises especially, when the quarter ends.

Quiz Answer: B. David Mamet was 36 when he wrote Glengarry Glen Ross (You can read the source article here).

How did you like today's story?

Today's email was written by Ken Kupchik and Steve Rado.

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