Hunt #20: Is It Time to Move On?

Timing Your Next Sales Career Move

Author

The Quota Hunter
November 05, 2024

Good morning hunters!

Today's newsletter covers a dilemna that many salespeople face: Should I leave my current company…or should I stay? In addition, you’ll find 20 recently captured HOT jobs on Quota Hunters I think are worth a peek, and words of wisdom to consider as you think about your sales career & journey.

Enjoy!

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Introduction

I recently spoke with a salesperson facing a common dilemma: should they stick it out in their current role or explore opportunities elsewhere? When it comes to sales, timing a career move is crucial because so much is at stake. From maximizing earnings to building a career-defining narrative, making the right move at the right time can shape your future in powerful ways. Here’s a breakdown of some factors to consider:

  • Capitalizing on strong momentum: Moving at a performance peak lets you bring recent wins into interviews, making you a more attractive hire. Companies value salespeople who can showcase recent, consistent success, so leaving on a high note is critical.

  • Avoiding missed earnings on a company upswing: Leaving during a company’s growth phase can mean walking away from significant earning potential, bonuses, or promotions. Gains you leave behind may not materialize at a new company (or may materialize slower than expected)

  • Preventing negative career gaps: Strategically timed moves prevent gaps or short stints on a resume. This consistency presents each career transition as a carefully considered, upward step rather than a result of instability or restlessness.

  • Mitigating internal risks before they impact you: Proactive exits before anticipated internal changes (like comp adjustments, territory shifts, or new competition) help protect your earnings and performance history. If you sense unfavorable changes ahead, consider transitioning sooner rather than later.

  • Ensuring continuous growth and skill building: Staying during growth phases allows you to hone valuable skills, gain insights, and broaden your experience, all of which make you a stronger candidate for future roles. Maximize these opportunities before considering a move.

  • Leaving with a Strong, Marketable Sales Story
    Your “sales story” — the narrative of your success and consistency — is a critical asset in your career. Leaving on a high note after achieving success over time enhances your marketability. Jumping ship too early can interrupt your story, while staying long enough to show measurable achievements builds credibility.

Background details

The salesperson I spoke with has built a successful career over the past decade, with a majority of their experience coming from tenures of 3+ years where they’ve consistently driven performance. Over the last three years, they’ve mostly exceeded expectations, except for one down year during COVID. This year, they’re on track to meet or exceed quota, and recent quarters have shown a strong increase in inbound leads, which is an encouraging sign for their business.

They’re aligned to a favorable industry niche, giving them an edge over some of their peers, and they’re earning a solid $100K+ base with realistic potential to reach $200K+ in total earnings. However, they’re also eyeing opportunities with companies offering “better” technology or services, faster growth, and potentially even higher earning potential.

So, what should they do?

Staying the Course: When It’s Worth It

If you’re having a great year and next year looks equally promising, it might be worth staying put. Sales is built on reputation, and maintaining a strong, stable tenure with consistently impressive results shows potential employers that you’re reliable and resilient. This can be worth more than a quick bump in earnings. Staying also means you’re already ramped up, with relationships and momentum that you’d have to rebuild at a new company.

Moreover, if you’re in a favorable market or territory, with a strong compensation structure, it can be risky to leave that for the unknown. The grass isn’t always greener, and making a jump without solid reason can lead to missed opportunities right where you are.

Considering a Move: When It’s Time to Look Elsewhere

If you anticipate significant changes on the horizon, like new leadership, a shake-up in comp plans, territory shifts, or a new competitor entering the market, it might be wise to look strategically at your options. Timing is essential — making a move before these changes impact your performance lets you exit on a high note with a strong sales story. Aim to make this transition between now and Q1, aligning yourself with recent successes that will appeal to potential employers while protecting yourself from declining stats if your suspicions about your current company become true.

Balancing Timing and Career Trajectory

Ultimately, it’s about balancing timing with where you want your career to go. If things are stable and growth is ahead, capitalize on your momentum. But if turbulence is on the horizon, start planning your exit to make the move on your terms.

Questions to Ask Yourself Before Making the Decision

  • How does my current role align with my career goals? Consider how your role contributes to your long-term growth. Are you gaining skills and building relationships that will enhance your career, or are you feeling stagnant? Are you in an industry that’s growing & popular (that I love)…or is it in decline?

  • What does the next 1-2 years look like here? If you’re optimistic about the near future, it could be worth staying to ride the upswing.

  • What would I miss if I left now? Think about the earnings, growth opportunities, and stability you might be leaving behind.

  • How marketable is my sales story right now? Evaluate how your recent achievements stack up. Would moving now showcase your best self?

Recently captured jobs found on Quota Hunters:

Quota Hunters is a community & job platform for salespeople that includes the ability to submit questions & get answers, more than 1,500 active sales jobs across the country, and so much more.

20 recent jobs that might be worth checking out:

Words of wisdom

I recently spoke with a SaaS client seeking an Enterprise AE with 10+ years of closing experience. They understand short tenures are common these days but still look for candidates with at least two stints of 3+ years.

For them — and most of our clients — two solid stints totaling around six years show reliability, commitment, and a track record of good performance.

Too often, I see resumes listing six companies in eight years. While these candidates can find roles, they may be overlooked by top-tier companies looking for proven tenure and stability.

That’s all for this week. Feel free to reply with any questions or feedback. Happy hunting!

Jay Green “The Quota Hunter”