How to Attack a Job Search in 2025 (Especially if You’re a Software Executive)

Let’s face the fact that executive job searching isn’t what it used to be.  It’s a lot tougher.

Gone are the days of waiting for recruiters to call or relying solely on your resume to do the talking. If you’re a VP or C-level leader in the software world, landing your next great role now requires the same strategic thinking you’d apply to product innovation or scaling a GTM engine.

Here are some suggestions that I often make to my candidates that are struggling with their search process:

Understand the New Playing Field

The software industry has changed. AI isn’t a “nice to have” anymore, it’s incorporated in everything. Growth-at-all-costs is out. Efficient, sustainable scaling is in. Hybrid work is more and more becoming the norm. To stand out, you need to show not just what you’ve done, but how you’re equipped to thrive in this new landscape.

Start with Strategy

Before updating your LinkedIn or pinging recruiters, ask yourself:

  • What spaces excite me?

  • Where does my experience move the needle? Where is my domain experience?

  • Which companies are right at the edge of something big and how can I help them get there?

That’s your bullseye.

Build Your Narrative

If you have worked with me as a candidate, you know that I require that you have your elevator pitch perfected before you sit in front of a hiring manager!!

  • 3-4 minutes outlining the progression of your career highlighting a few strong accomplishments and sell yourself.

  • Talk about where you’ve built and scaled elite teams—especially under pressure.

  • Explain your track record of navigating tough market conditions.

Use AI—Smartly

Networking isn’t dead, but it’s evolving. Use AI tools to:

  • Spot fast-growing companies that align with your skillset.

  • Track leadership changes that could signal opportunity.

  • Surface second-degree connections who can open doors.

Polish Your Digital Presence

Your LinkedIn is just the start. Think bigger:

  • Share insights through articles or commentary on trends you actually care about.

  • Jump into discussions in niche tech communities or forums.

  • Show your thought leadership in areas like AI integration, product-led growth, or digital transformation.

Partner with Search Firms—Strategically

Not all search firms are created equal. Look for ones that know the software landscape. Make it easy for them to advocate for you:

  • Be clear on your story and give a strong elevator pitch (I sound like a broken record here but it’s just SO important). Sell yourself to the search firm.

  • Share specific wins that solve real business problems.

  • Keep the relationship warm—even when you’re not actively looking.  This means response to top recruiters even when you are employed and happy, just to build that long-term relationship.

Do Your Due Diligence

It’s not just about the offer, it’s about the fit. Dig into:

  • Their tech debt and modernization plans.

  • How ready they really are for AI.

  • Who’s on the leadership team—and how decisions get made.

  • Burn rate and runway (especially for PE or VC-backed companies).

Negotiate Like a Strategist

Yes, compensation matters. But so do:

  • Execution authority an autonomy.

  • Alignment with leadership and board.

  • Defined success metrics.  I always ask my clients - “What specific outcomes would make you say, six months from now, ‘Wow, we hired the right person’?”

Don’t just negotiate numbers, also negotiate clarity.

Build Your Inner Circle

You don’t have to go it alone. Lean on:

  • Peer networks who get it.

  • Trusted advisors to help you see your blind spots.

  • Executive coaches who specialize in the software world.

Stay Engaged

Your best negotiating position? Thriving where you are.

Keep leading. Keep learning. Keep growing. You’ll have more options, and more leverage for when that perfect offer comes.

 

Bottom line: In 2025, landing your next executive role means bringing the same strategy and discipline to your search as you do to your work.

Let’s make your next move your best one yet.

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How to Resign: Lessons from Judy Over the last 25 Years of Executive Recruitment