Should You Leave Your Sales Job? How to Know If It's Time to Move
"I think it's time to move. But I'm not sure."
I hear a version of this question constantly. I coach senior sales leaders who come to me with exactly this. Their company had restructured. Their company territory and team have changed. The strategic scope they’ve built up was shrinking. On paper, all the classic signs that it's time to go.
But when we talk it through properly, the honest answer is, it depends.
The Question I Hear All the Time: "Should I stay or should I go" feels like it should have a clean answer. It rarely does.
Reasons to Stay (For Now)
NEED A SECOND SET OF EYES ON YOUR CV AND LINKEDIN?
"Should I stay or should I go" feels like it should have a clean answer. It rarely does.
Tenure brings security, and in this market, security has real value.
Long service can mean a meaningful redundancy package if the worst happens, and walking away forfeits that entirely.
Restructures often create unexpected visibility. Stepping up during uncertainty can accelerate a sales career faster than a clean move to a new employer would.
The market for sales roles is genuinely tough right now: fewer open roles, more competition for each one, and longer search timelines than people expect.
A move made in frustration, rather than from a clear-eyed read of the situation, can leave you worse off than staying put.
Reasons to Go
Your growth has genuinely stalled and there's no realistic path forward in your current sales role — staying is just postponing a decision you'll eventually have to make anyway.
You're significantly underpaid for the deals you're closing or the quota you're carrying, and there's no appetite from the business to address it. That gap will only grow.
The culture or leadership has shifted in a way that no longer aligns with how you want to work or sell.
Your role has contracted to the point where you're losing skills rather than building them — that's a career problem, not just a job problem.
You wake up every morning dreading the day. That's not a market problem. That's a you-and-this-job problem. No market condition justifies staying somewhere that's affecting your wellbeing.
The Real Question Behind "Should I Stay or Go"
The nuance most people miss is that this decision isn't binary. The real question is: what is this actually about?
Is it frustration that will pass? A values mismatch that won't? A market moment worth riding out? Or a situation that's genuinely costing you, financially or otherwise?
Getting clear on which of those it is matters more than rushing to a decision either way.
IN SUMMARY:
Get ready to move, rather than deciding to move on impulse. Do the work of understanding whether what you're feeling is temporary frustration or a genuine signal. Weigh the real costs of staying against the real costs of going. And if every morning is telling you something different to what your head is telling you, trust that too.
Annalie Graham, July 2026
About ANNALIE GRAHAM
As Associate Director at Armstrong Lloyd, I specialise in helping B2B businesses build teams that truly deliver. Over the past 10+ years, I've worked with B2Borganisations, including technology, manufacturing, and professional services businesses to connect them with the senior sales and marketing leaders and rising stars who can drive growth.
I believe recruitment is about more than filling a vacancy – it's about understanding your career goals and partnering with you to get there. Whether you're a Sales Director eyeing your first CRO seat, building out a business development function, or looking to step into RevOps leadership, the people I work with value my market insight, straight-talking approach, and ability to open doors to opportunities that aren't advertised.
I'm a regular presence at industry events, staying close to the conversations and trends that matter most to sales leaders. Whether it's the impact of AI on the sales function, evolving go-to-market models, or what it takes to stand out for your next senior role, I'm passionate about helping ambitious sales professionals navigate change and find the roles where they can make their mark.