Why Tech Sales Superstars Leave Even After Years of Loyalty

03 February 2026

By Rebecca Scheepers

Why Tech Sales Superstars Leave Even After Years of Loyalty

We hear this all the time: "They’d been here five years, progressed through the ranks, and we know they’re probably underpaid… but we’re happy to pay market rate for their replacement.

If you work in tech sales, that sentence probably feels uncomfortably familiar.

Not because it’s malicious, but because it’s common.

How people quietly fall behind market pay

In many tech companies, salary increases are handled incrementally. A percentage here. A small bump there. On paper, it looks financially sensible. From a CFO’s perspective, keeping salary inflation low feels prudent. But over time, something happens. High performers grow faster than their pay:

  • Responsibilities increase

  • Revenue impact grows

  • Expectations rise

  • Titles change

Yet salary often lags behind the actual role being done. After a few years, you can be performing at a significantly higher level than your original job, while still being paid as if you’re one or two steps behind.

LinkedIn changed the balance of power

Years ago, many people didn’t really know what they were worth. Salary information was opaque, and opportunities weren’t constantly visible. That’s no longer the case. Today:

  • Recruiters reach out regularly with salary ranges

  • Peers openly discuss compensation

  • Market data is easier to access

  • Job ads are more transparent

It doesn’t take long for someone to realise they’re underpaid relative to their impact. At that point, loyalty starts to erode because the gap becomes hard to justify.

Why counteroffers don’t work like they used to

When underpaid top performers resign, many companies scramble to respond with a counteroffer. However, candidates are far more savvy now.

They’ve seen this pattern before:

  • Years of incremental increases

  • A sudden jump only when they threaten to leave

  • Promises of future progression that didn’t materialise previously

By the time a counteroffer appears, trust has often already been damaged. For many people, it confirms something they already suspected: "The money was available, it just wasn’t offered until I was halfway out the door."

The replacement paradox

One of the hardest truths in tech sales is this: Companies are often willing to pay full market rate or more for someone new, while hesitating to adjust the salary of someone who has already proven their value.

From the outside, it looks illogical.
From the inside, it’s often the result of outdated pay structures and fear of setting precedents.

The key lesson for candidates

If you’re a high-performing sales professional, you should be paid for the role you’re doing today, not:

  • For the role you were hired into

  • A percentage uplift on last year’s salary

Progression without pay alignment is not real progression, it’s just added responsibility. If you are consistently outperforming your peers, taking on responsibilities beyond your title and being told you’re “valued” but not seeing that reflected financially, it’s reasonable to question whether your compensation still matches your market value.

Staying loyal to a company that invests in you fairly makes sense. Staying loyal while quietly falling behind the market rarely does.

Final thought

Most people don’t leave great teams because they want to. They leave because the gap between contribution and compensation becomes impossible to ignore. Knowing your value and expecting to be paid accordingly is professional, not disloyal.

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