Early to mid-career product managers in Silicon Valley often dream of landing the perfect job—high comp, strong team, great product, and a clear path for impact. But what if I told you that sometimes the smartest move is walking away?
That was the case for Elizabeth Hague, a seasoned marketing leader with two successful exits under her belt. She recently turned down a VP of Marketing role that came with a $350K offer, and her reasoning provides invaluable lessons for navigating today's brutal job market.
This post is packed with her insights, specific examples, and actionable advice to help you avoid career missteps and make smarter choices as you navigate your next big move.
Lesson 1: "You Have to Market Yourself"
One of the first points Elizabeth made in our conversation was how ironic it is that even experienced marketers struggle to market themselves. And that’s true for product managers, too. The hiring market is not what it was in 2017, when smart generalists could land jobs with strong interview skills and broad expertise. Today, hiring managers want hyper-specific, battle-tested experience in their exact industry and problem space.
"It's an employer’s market right now, especially in B2B SaaS. Any small thing can be a reason for rejection," Elizabeth said. "If you're not putting real effort into marketing yourself, refining your personal brand, and strategically positioning your experience, you're already behind."
Takeaway: If you're on the job hunt, think about how you’re presenting your skills. Are you crafting your story in a way that aligns with what hiring managers are actually looking for? Use data, case studies, and specific examples to sell your impact—not just a list of job titles.
Lesson 2: Beware the "Cinderella Fit" Trap
Elizabeth and I both noted how today’s hiring market is much more rigid than in past years. "This is not a market where a hiring manager says, 'Oh, this person is smart and driven, they can figure it out,'" I said. "They want someone who has done this exact job before, maybe even at a bigger scale. They can afford to be that picky."
This is why so many PMs struggle to break into new domains or level up into leadership roles. Companies often have 500+ applicants per job, so they optimize for the path of least resistance—hiring the safest, most obvious choice.
Takeaway: If you’re trying to make a jump—whether it’s into leadership, a new industry, or a new function—you need to be strategic. Build bridges, seek out internal opportunities to gain experience before you switch, and cultivate relationships with decision-makers who can vouch for you.
Lesson 3: How to Spot Red Flags in Job Offers
Elizabeth’s experience turning down a VP job was a masterclass in knowing when to walk away. She identified multiple red flags in her interview process:
Unrealistic Growth Goals: The company expected to 10X revenue in 12 months but had no product marketing team, no demand gen, and had shut off all paid ads.
Underinvestment in Key Functions: The entire marketing budget—including headcount—was just $1M.
High Turnover: The previous VP was fired, and the team was described as "low performers." That’s often code for "leadership doesn’t know how to support and develop talent."
CEO With a Misaligned Vision: "When I asked if these aggressive goals came from the board or him, he said they were his own," Elizabeth noted. That suggested an executive with unchecked expectations.
"If I didn’t have my internal list of non-negotiables, I might have ignored these signs and taken the job," she admitted. "It’s really easy to rationalize a risky decision when you're in the moment."
Takeaway: Before you take an offer, do your diligence. Ask about resourcing, past performance, and leadership expectations. If the math doesn’t add up, trust your gut.
Lesson 4: The "Honeymoon Discount" and Why You Should Apply It
Whenever I coach product managers on career decisions, I recommend applying a 30% honeymoon discount—whatever you think the job is, assume it’s at least 30% harder, messier, and more dysfunctional than it appears.
"No matter how much diligence you do, there will always be surprises once you're inside," I said in our discussion. "And I have never seen a situation where a job turns out to be better than expected."
Takeaway: When evaluating an offer, don’t assume best-case scenarios. Consider worst-case risks and be sure you’re comfortable with them before signing on.
Lesson 5: When It’s Okay to Take a "Less Than Ideal" Job
Not everyone has the luxury of turning down offers. Some people need to get back in the game, rebuild confidence, or simply pay the bills.
Elizabeth acknowledged this, saying: "I got a few angry comments on my LinkedIn post—people saying, 'Must be nice to turn down that money!' And I get it. But I wasn’t willing to sacrifice my health and sanity for a role I knew was set up to fail."
I also noted that some people take jobs just to “ride the cow while looking for the horse” (an old Cantonese saying). Some PMs strategically take an imperfect job to get back in the market while continuing their search.
"It’s a totally valid approach, as long as you go in eyes wide open and set your own expectations accordingly," she said.
Takeaway: There’s no shame in taking a suboptimal job if it meets an immediate need. Just be clear on your own boundaries and don’t let short-term survival mode dictate long-term career decisions.
Final Thoughts: The Career Playbook for Today’s PMs
The job market today is tougher than it’s been in years. But that doesn’t mean you should settle for roles that will burn you out or set you up for failure.
Key takeaways:
✔ Market yourself strategically—don't assume your resume speaks for itself.
✔ Be aware of how the hiring market has changed—"Cinderella Fit" roles dominate.
✔ Spot red flags early—don’t wait until you’re six months in to realize the job is a disaster.
✔ Apply the "honeymoon discount"—assume every job will be harder than it looks.
✔ If you must take a less-than-perfect job, do it intentionally and keep your options open.
If you're a product leader looking for 1:1 career coaching, check out TomLeungCoaching.com. And if you’re at a startup needing product strategy consulting, visit PaloAltoFoundry.com.
Follow Elizabeth on LinkedIn.
As always—let’s get back to work.
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