The Mid-Level Leadership Trap: Why Product Leaders Are Stuck in Career Limbo

Mid-level PM leaders like Directors, GPMs and Head of are really struggling in this market.

Here’s why:

𝗧𝗛𝗘 𝗠𝗜𝗗-𝗟𝗘𝗩𝗘𝗟 𝗟𝗘𝗔𝗗𝗘𝗥𝗦𝗛𝗜𝗣 𝗧𝗥𝗔𝗣 𝗜𝗦 𝗥𝗘𝗔𝗟

In today’s job market, mid-level leaders (like Group PMs and Directors) are in a bit of a pickle.

The supply of open VP roles is shrinking, while companies’ demand for top-tier candidates is rising. Mid-level leaders are caught between taking a step back to IC roles (which can feel like a demotion or failure) or experiencing uncertain job searches.

Even if you’re tempted to switch back to IC, you’ll likely take a hit on compensation. Difficult decision, right?

Let’s break down the three big challenges mid-level leaders are facing ( in collaboration with Eugene Segal):

𝗖𝗛𝗔𝗟𝗟𝗘𝗡𝗚𝗘𝗦 𝗙𝗔𝗖𝗘𝗗 𝗕𝗬 𝗠𝗜𝗗-𝗟𝗘𝗩𝗘𝗟 𝗟𝗘𝗔𝗗𝗘𝗥𝗦

→ Visibility

It’s a tough crowd out there. Getting noticed? Even tougher.

↳ You’re competing with the best of the best, and standing out is no easy feat.
↳ Everyone wants a VP title, but with limited spots, you can feel like you’re lost in the shuffle.

→ Career Dilemma

Stuck between two choices that don’t feel quite right.

↳ Moving back to an IC role feels like you’re stepping down, even if the work excites you. ↳ On the other hand, staying stuck in a role with no path to VP means your growth plateaus.

→ Financial Impact

After all, it also takes a financial toll on your life and career.

↳ A switch to IC often means a pay cut, which isn’t ideal for many obvious reasons.
↳ There’s also the risk of staying too long in same role, which can affect long-term earning potential and career growth.

So, how do you climb out of the mid-level leadership trap? Here’s a roadmap to help:

𝗡𝗔𝗩𝗜𝗚𝗔𝗧𝗜𝗡𝗚 𝗧𝗛𝗘 𝗧𝗥𝗔𝗣

→ Build a Strong Network

Put conscious daily efforts into increasing your opportunities luck surface area by putting yourself out there.

↳ Engage with VCs, recruiters, and peers — the best roles often don’t hit the job boards.
↳ Don’t sleep on LinkedIn; share insights and make sure your value is visible to the right people.

→ Enhance Specialized Skills

Keep sharpening your sword every single day.

↳ Focus on niche, high-demand skills to boost your Candidate-Market Fit.
↳ Keep evolving. Attend workshops, get the right certifications, and stay ahead of the trends.

→ Seek Out Mentorship

Sometimes, taking help from someone who has successfully crossed your path is the best thing you can do.

↳ It helps you shorten your experimentation curve and navigate this tricky phase.
↳ They can provide introductions, advice, and guidance that can unlock doors you didn’t know existed.

If you want to dive deeper into navigating this trap and preparing yourself for success, refer this guide.