The Strategic "Job-Hopper"

How to evaluate when it's time to move on

👋 Hi, it’s Kaylee Edmondson and welcome to Looped In, my newsletter exploring demand gen and growth frameworks in B2B SaaS. Subscribe to join 1k+ readers who get Looped In delivered to their inbox every Sunday .

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Every few years on the job, like clockwork, something used to fire in my brain. All of the sudden I’d start to feel a push with my current gig. You know where I’m going with this. That one manager would micro-manage one time too many. That colleague across the hall sounded like he was talking louder and louder on calls. Somehow those florescent lightbulbs would start buzzing and glitching more often than they had the days and weeks prior. (Yes, this was back in the “in-office” days.) I’d start to feel…stuck, not stretched. Like my career wasn’t progressing fast enough, or like I was no longer challenged with my current projects. Like quicksand, my thoughts would start consuming me leaving me wondering if I was falling behind.

And almost always when that happens, magically, there’s some recruiter in your LinkedIn DM’s pushing this narrative that she’s been searching far and wide for the “needle in the haystack” and somehow I’m lead to believe that needle is me. That’s the pull. She’s saying all the right things. Really convincing me the grass is greener. Somehow everything at this new, beaming startup is the answer to all the grievances I have with my current gig. And I’m a sucker for romanticizing the thrill of startup life and being “chosen” so…here we go.

I’d make the jump.

Only to realize, well, shit. The insides of this company actually aren’t all peaches and rainbows like I was led to believe. Or, gosh, I now have 2 bosses that generally have conflicting opinions. And, dang, this industry actually moves and operates entirely differently than a few of the previous gig’s components that I actually enjoyed more than I realized. Or worse yet, this larger, more-funded company now has 800+ employees and has so much red tape internally for approvals that you could theoretically start up a profitable Christmas tree farm faster.

There might be some slight exaggerations there, but the gist remains true. LinkedIn, just like most other social media platforms, is a highlight reel for your career (mostly). Getting on and doom-scrolling through everyone’s new gigs, promotions, winning campaigns, funding rounds, etc. is hard to see if you’re feeling stuck in your own gig.

Here’s what I’ve learned either the hard way on my own, or from others who are far smarter than me.

For context, the current state of B2B SaaS marketing career mobility largely relies on:

• Your ability to master existing and emerging skills (think tech, programs, tactics)

• Your ability to hit company pipeline/revenue numbers

• The ability to socialize the impact cross-functionality

Which undoubtedly is a high pressure role for any one person, and I’ve found that most companies perceive the Head of Demand Gen to be the sole person in charge of driving “inbound sourced” pipeline. One person. Demand Gen is still definitely seen as a function and not an organization-wide initiative.

So the thesis typically becomes, you as a demand gen marketer, need to be able to either move UP or move ON every 2 years in order to not fall behind from a compensation perspective, but is that the only thing to consider here?

Do I Stay, or Do I Go

I’ve had this draft article sitting in my Substack for weeks now. I keep coming back to it with new resources or a different spark of inspiration. Last week a snippet from Kyle Lacy’s Revenue Diaries hit me like a ton of bricks. If you aren’t subscribed, you should be. It’s this excerpt here:

You need to distinguish between growth and drain.

Not all challenges are created equal. Some build your career. Some make you a better practitioner. Others drain the life out of you. Here’s how to tell the difference:

✅ You learn something valuable. Even when it’s tough, you build skills, confidence, or experience to serve you long-term.
✅ It aligns with your goals. The challenge is part of a bigger picture—whether it’s career growth, leadership, or a skill you want to master.
✅ There’s a clear path forward. You can see how pushing through leads to improvement or opportunity.
✅ It’s hard, but you feel accomplished. Even if it sucks at the moment, you come out on the other side feeling stronger.

❌ No real learning. The challenge feels repetitive, pointless, or like busywork.
❌ It’s outside your control. The problem stems from poor leadership, bad culture, or broken systems that won’t change.
❌ It doesn’t align with your goals. You’re struggling for something you don’t care about or see value in.
❌ You feel stuck, not stretched. Instead of a sense of progress, you feel like you’re spinning your wheels with no real wins.

An 80/20 matrix like this can help you objectively reflect on your current scenario. Perhaps you’re actually experiencing a moment of stretch with your gig. In which case, the payout of staying is likely far greater than the short term pressure of being stretched. Or maybe it really is time to move forward?

Red Lights; Green Lights To Making a Move

I showed my cards earlier and said I’m a sucker for romanticizing my career. And it took me a few hard learnings early on to recognize I need a method to my madness for making career moves. For me, it’s as simple as a red light; green light checklist and a scorecard.

After a few years of working in SaaS I came to learn I am particular about a few things based on my skill set, and where I personally feel I can contribute the largest impact to an org. Those learnings helped me shape my own red and green lights. Each of these company attributes lives in a spreadsheet and each company I’m evaluating are held to the same requirements. The value is either, true, false, or “to be determined” which just means I still need to get to the bottom of it.

Red Flags

🚩 Multiple leadership changes in 6 months
🚩 Declining market share / market relevance
🚩 Solving a problem I care about
🚩 Frequent restructuring
🚩 Budget cuts in marketing
🚩 High team turnover
🚩 Unclear company vision
🚩 Limited career progression
🚩 Poor back-channeling references
🚩 Greater than 500 employees in size
🚩 Poor operating margins

Green Lights

✅ Series A+ funding secured
✅ Strong product-market fit
✅ Expanding marketing budget
✅ Clear org design
✅ Industry recognition
✅ Positive customer feedback
✅ Diverse leadership team

If a company makes it past red lights; green lights, by this point you’re typically further in their interview process and can then start scoring each opportunity against another. Obviously make these your own

Scoring Your Next Opportunity (1-5 points each)

□ Learning potential
□ Ability to solve a ‘real’ problem
□ Technology exposure
□ Team quality
□ Company growth trajectory
□ Compensation package
□ Work-life blendability
□ Culture add
□ Career clarity
□ Industry positioning

Minimum total score: 35/50

Just like every brand you work for has an ICP fit; think of this like finding your own ICP fit for your next gig. Or….if we want to open this can of worms, maybe this is a broader opportunity for you to question putting all of your eggs in one basket and consider the portfolio career path. It took me a long time to finally admit that the ‘comfort of a W-2’ was really a false narrative I’d been feeding myself. And maybe this resonates with you, too.

Either way, you’ve got this!

Whether it’s a rut you’re stuck in that’s got you feeling a push, a new shiny gig that’s pulling you in, or a sudden urge to totally jump ship ⛵️ and create a multi-revenue stream income for yourself. Trust that you’ve got this. And hopefully these thoughts above will help guide you.

See you next week,
Kaylee