So several times now I’ve seen the #1 sales rep that was just crushing it for quarter after quarter, then a few years down the road, later become one of the lowest performers. From #1 to the bottom of the leaderboard. And the fall often happens pretty quickly, even if at the time, it’s hard to see clearly.
Not usually. Usually, the top reps, the #1 and #2 reps, hit sort of an elite level of understanding of the process, prospects, and industry. They crush the objections, they know how to pitch all the stakeholders, and they know the critical strengths and weaknesses of the product they sell. Usually, they stay elite as long as they stay.
So most of the time, if you back them and keep investing in them, pay them well, and to some extent, just leave them alone, your top 1-2 reps will stay your top performers.
But now time has gone on, and I’ve seen a few times, the #1 rep stumbles, and often quickly. And slides down the leaderboard fast. The pattern has accelerated in 2025-2026 specifically, for reasons we’ll get to.
Why does the #1 rep … stumble after 12, 24+ months? I’m not 100% sure but here’s what I’ve observed for root causes:
#1. It Just Got Harder
We’ve seen this a lot the past 18-24 months where selling just got harder at most B2B startups. Often, the best further pull ahead from the rest when it gets tougher. But sometimes, they just don’t want to, or aren’t able, to step up. They were good with how it was. And they just stop closing.
The 2026 version of “harder” is also qualitatively different. The new B2B buyer has a ChatGPT tab open during the demo. They’re fact-checking your top rep’s claims live. They’ve researched your top three competitors before the call. The polished-but-shallow demo your #1 rep perfected over five years is getting exposed in real time. Reps who built their game around great FUD and a smooth pitch but never went deep on the actual product are particularly exposed. The reps thriving in 2026 are the ones with deep product knowledge, intellectual honesty about where competitors are genuinely strong, and comfort going off-script. If your #1 was great at the old game and the game changed, the leaderboard reorders fast.
#2. Don’t Want to Put in The Time Anymore
I’ve also seen a few #1 reps stumble when they coasted too much. Not intentionally, they were still working it. But once they could hit their number regularly, they dialed it back a bit. Vacationed more. Took on more side hustles. Slowed down their response time to prospects. Didn’t do the extra demo. That complacency sometimes is fine in the best reps. But sometimes, it’s a step too far. And their proven playbook no longer works when they are working 80% as hard at it as before.
The best reps still work harder. Genuine curiosity, extra research, extra calls, extra discovery. AI didn’t change that. If anything, AI made the grinders more productive and the coasters more obvious. Because when AI is doing the qualification, the data entry, the sequence sends, what’s left is the part that actually requires the rep to show up and do the work. If they’re not doing that part, there’s nowhere to hide anymore.
#3. They Don’t Want to Adapt
This is the one everyone needs to be aware of. A new VP of Sales? An obvious risk with your top performers. Your biggest competitor raises $100M? Sometimes tough to get your head around. The market changes quickly? Sometimes, it’s just too much change. The best reps do want consistency. It’s how they thrive. Just be aware not everyone can adapt. At least, try to minimize the disruption on your top performers wherever you can.
In 2026, “adapt” includes adapting to AI in their workflow. The reps using Gong/Granola transcripts, AI-drafted follow-ups, AI research agents on every account, are running circles around the ones who refused to learn the tools. We’ve seen this at SaaStr too. The reps who leaned into the new stack saw their output grow. The ones who insisted on doing it the old way fell behind quickly. Whatever your view on AI in sales, the reality is the productivity gap between an AI-augmented rep and a non-AI rep is now real and growing every quarter.
#4. Their Patch Shrinks, Even If Just a Bit
Sometimes a rep is #1 because they are great, but also often because they are early. They end up with a large patch, a large database of names, a ton of folks to upsell and renew. Later, some of that gets redistributed to new folks. And they decide to move on. Even if they still have plenty.
The 2026 wrinkle: a new redistribution is happening that wasn’t happening before. The easy/warm leads, the inbound, the long tail of mid-market re-engagement, all of that is increasingly flowing to AI agents instead of to your #1 human rep. At SaaStr, our AI-sourced pipeline grew 11x year-over-year while our best human rep grew 82%. Both growing. But the AI is closing the gap fast. So your #1 rep may look at their pipeline and notice the warm easy stuff isn’t there anymore. The tougher, more complex deals are. That’s the right strategic move for the company. It also means your top human reps are doing harder work for the same number, and some of them won’t like that. Worth being honest about.
#5. They Didn’t Build the AI-Era Playbook
This is the new one for 2026. The best reps used to win because they had the best Rolodex, the best objection-handling, the deepest product knowledge, and the most disciplined cadence. All of that still matters. But the new top performers are also building a personal AI stack. They have their own custom GPTs trained on past discovery calls. They run AI research on every prospect before the first call. They use AI to draft and personalize multi-channel sequences in minutes. They join calls with an AI co-pilot listening in real-time, surfacing competitive intel and objection counters as the conversation happens.
If your #1 rep from 2024 isn’t doing any of that, they’re competing against reps in 2026 who effectively have a senior SDR, a research analyst, and a sales engineer running silently alongside them on every call. The math doesn’t work. They’ll fall.
Not everything here is actionable. Startups change. They evolve. They become scale-ups. They go from $1M to $10M to $100M to $1B in ARR. They IPO.
But I don’t know any founders who didn’t wish they could have kept their top performing rep performing longer. At least at the top level.
The best advice I have: shelter them as much as you can, try to keep them in their zone, and at the same time, gently push them toward the new tools. The best ones will adapt. They always do. The ones who can’t or won’t, you’ll know within a quarter.
And realize, some may not be #1 anymore as the markets and your stage change. That’s part of the game. Loren Padelford, the CRO at Slice, said it well: sales leadership is pure science, not magic. Revenue is just an output. The inputs are what reps actually do. When the inputs change, the outputs change. Your #1 rep was elite at one set of inputs. The question is whether they’re willing to learn the new ones.
