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What I'm Seeing With Senior Tech Executives Right Now: The Uncomfortable Truth About $450K Roles in Late 2025

Bill Heilmann
What I'm Seeing With Senior Tech Executives Right Now: The Uncomfortable Truth About $450K Roles in Late 2025

Here's what senior tech executives are really asking.

What I'm Seeing With Senior Tech Executives Right Now: The Uncomfortable Truth About $450K Roles in Late 2025

I've been talking to a lot of $300K-$500K executives lately.

VPs. Directors. Senior Individual Contributors at Microsoft, Salesforce, Amazon, Google, Meta.

These aren't struggling professionals. They're accomplished leaders who built successful 20+ year careers on expertise, process management, and organizational knowledge.

But here's what I'm noticing in late 2025: Something fundamental has shifted.

They're not panicking. But they're looking over their shoulders.

And the calls I'm getting? They've changed dramatically in the last six months.

The Shift in the Conversations

Six months ago, the calls sounded like this:

"Help me get promoted to VP."

"How do I position myself for the SVP role?"

"What's the path to C-suite at my company?"

"I want to maximize my next compensation package."

Career advancement. Title progression. Salary optimization.

Now, the calls sound like this:

"Help me understand what's coming."

"What roles actually survive this?"

"How do I position myself so I'm not the next layoff?"

"What's my backup plan if this doesn't work out?"

It's not about climbing anymore. It's about survival.

And more importantly—it's about understanding what's actually happening beneath the surface of the "AI transformation" rhetoric their companies keep repeating.

What They're Seeing (But Not Always Saying Out Loud)

These executives see the signs every day:

The org changes that don't get fully explained. Layers collapsing. Teams consolidating. Roles that used to require three people now need one—plus AI tools.

The "efficiency mandates" from leadership. Do more with less. Increase productivity. Optimize headcount. All code words for "we're replacing human work with AI work."

The promotion freezes that have no end date. "We're not backfilling that role." "We're restructuring before making any moves." "Let's revisit this next quarter."

The subtle questions about AI adoption. "How are you using AI in your workflow?" "What percentage of your team's tasks could be automated?" "Show me how you're leveraging these new tools."

The vesting schedules that create massive anchors. $200K in RSUs vesting next year. $150K the year after. $300K in stock options that hit in 18 months.

Walking away from unvested equity feels impossible. So they stay put and hope this AI wave passes them by.

The Psychology I'm Observing

What's fascinating—and concerning—is the psychological pattern emerging:

Pattern 1: The Identity Crisis

For 20+ years, their identity has been tied to their corporate title and the organizational power structure.

"I'm a Senior Director at Amazon."

"I'm a Principal Engineer at Google."

The badge. The team. The budget. The influence.

Their self-worth is deeply embedded in these external markers. Losing the W-2 isn't just about money—it's an identity crisis.

The uncomfortable question they're avoiding: "Who am I without the badge?"

Pattern 2: The Golden Handcuffs Trap

They see the RSUs. The vesting schedules. The "next cliff" of stock options.

The math feels compelling:

  • Stay 18 more months = $300K in vested stock
  • Leave now = forfeit all of it
  • Stay seems like the only rational choice

But here's what they're not calculating: The opportunity cost of staying in a role that's being structurally eliminated.

That $300K in unvested RSUs might disappear entirely if the role gets restructured or eliminated before it vests.

Pattern 3: The Warm Body Comfort

Here's something nobody admits out loud: Being a $450K "warm body" in a large org is actually comfortable.

The system carries them. The calendar is full. The Zoom meetings provide structure. The paycheck arrives every two weeks.

There's psychological safety in letting the organization define your purpose, your schedule, your mission.

The entrepreneurial path—defining your own structure, generating your own clients, justifying your premium value every single day—is terrifying by comparison.

The Brutal Reality They're Starting to Accept

The layoffs of 2023 were about over-hiring post-COVID and cost-cutting.

The layoffs of 2024 and into 2025? They're about structural replacement.

AI isn't just making people more productive. AI is making entire layers of management and process execution obsolete.

The Roles at Highest Risk

Based on what I'm seeing and the data emerging in late 2025:

Entry-level coders: Routine coding, documentation, basic QA—all easily automated.

Mid-level managers: Process orchestration, status reporting, roadmap management—AI handles this now.

Director-level middle managers: Managing people who manage process. Both layers are collapsing.

The "process executor" at any level: If your value is executing established processes rather than creating strategic value, you're vulnerable.

The Question Haunting $400K+ Senior Directors

I'm getting calls from Senior Directors earning $400K-$600K total comp asking versions of the same question:

"Is this salary sustainable?"

They know the answer. They just don't want to say it out loud.

The reality: These massive compensation packages were paid for two reasons:

  1. Managing large, complex organizations
  2. Preventing them from jumping to competitors

As organizations flatten and AI takes over process management, both justifications erode.

The new standard: To sustain $400K+ compensation, you must become an AI-leveraged executive who drives 10X strategic results by integrating AI across your business unit.

If you're perceived as managing people and process—tasks AI now handles—your time is limited.

What's Actually Being Hired in Late 2025

Here's what many executives miss: The money isn't disappearing. It's relocating.

The median total compensation for AI Executives is $1.6 million. The 75th percentile reaches $2.5 million.

But these aren't traditional roles. They're:

Chief AI Officers (CAIO): Managing AI governance, ethics, deployment frameworks, risk mitigation. Salary range: $376K+ and climbing.

AI Strategy Executives: Not managing people, but integrating AI solutions to drive massive P&L impact.

Fractional Executives: High-value consultants earning $10K-$15K per month retainers across multiple companies, often exceeding their old W-2 income with more control and less risk.

The old role: Senior Director of Engineering (managing 5 teams, optimizing agile process, delivering roadmap).

The new role: Senior Director of AI (driving 10X strategic results, integrating AI across the business unit, mitigating AI risk).

Same title. Completely different function. Only one is getting paid.

The Questions Smart Executives Are Now Asking

The smartest executives I'm talking to aren't bailing immediately. But they're asking fundamentally different questions:

"What roles actually survive AI displacement?"

Roles focused on strategic thinking, critical judgment, emotional intelligence, creativity, and P&L impact. Not roles focused on process execution and people management.

"How do I position myself as irreplaceable?"

By becoming AI-fluent. By driving measurable business outcomes using AI tools. By shifting from managing process to creating strategic value.

"What's my backup plan if this doesn't work?"

Transitioning to high-value fractional consulting. Building a diversified client base. Creating multiple income streams instead of relying on a single W-2.

"How do I de-risk my income before I'm forced to?"

Starting the transition now—while employed—rather than waiting until after a layoff when negotiating leverage is zero.

The Uncomfortable Truth

If you're a senior tech executive reading this and thinking "this sounds like me," you're not alone.

The psychological barriers are real:

  • The identity tied to your corporate title
  • The golden handcuffs of unvested equity
  • The comfort of organizational structure
  • The fear of entrepreneurial uncertainty
  • The difficulty of constantly selling yourself

But here's what you need to understand:

Your $450K W-2 is not the safety net you think it is. It's actually a single point of failure with increasing structural risk.

The traditional corporate career path for senior tech executives is experiencing a fundamental collapse driven by AI. The timeline is accelerating faster than most people realize.

What This Means for You

I'm not here to scare you or push you down one path.

If you want to land another $450K W-2 role, I'll help you do exactly that. If you want to double-down on finding the next corporate position, we can build that strategy.

But I'd be doing you a disservice if I didn't share what I'm seeing:

The executives who thrive through this transition will be the ones who:

1. Face reality early rather than hoping the wave passes them by

2. Build AI fluency and leverage to become strategically valuable, not operationally redundant

3. Diversify their income sources before being forced to, not after

4. Pivot from process executor to value creator with quantifiable P&L impact

5. Consider alternative models like fractional executive work that provide more control and less risk

The Path Forward

The executives I'm working with who are handling this best aren't the ones with the most impressive resumes or the highest current salaries.

They're the ones who are asking the right questions and willing to challenge their assumptions about what career success looks like in the AI era.

They're exploring:

  • How to position themselves as AI-leveraged strategists
  • What fractional executive work actually looks like
  • How to build a Solo 401(k) that allows greater retirement contributions than corporate plans
  • What it means to shift from external identity (title/badge) to internal authority (solved problems/impact)
  • How to structure retainer-based consulting that generates comparable or better income with less risk

This isn't about abandoning the W-2 path. It's about making an informed decision with your eyes wide open about the structural risks and alternative options.

What I'm Not Saying

I'm not saying:

  • Every tech executive will be laid off
  • You should quit your job tomorrow
  • Corporate careers are dead
  • Everyone should become a consultant
  • AI will replace all human work

What I Am Saying

I am saying:

  • The rules have fundamentally changed in 2024-2025
  • AI is driving structural transformation, not just efficiency gains
  • Process-based roles are at existential risk
  • Massive compensation requires new justification
  • Smart executives are asking different questions
  • You deserve to understand what's actually happening
  • Alternative paths exist that you may not have considered

The executives who make informed decisions now—whether that's staying and adapting, or transitioning to something different—will fare better than those who ignore the signals until they're forced to react.

The Bottom Line

If you're a $300K-$500K senior tech executive and you've felt that subtle shift—the org changes, the efficiency mandates, the vesting schedules that anchor you, the nagging question about whether your role survives this—you're not imagining it.

The landscape is fundamentally changing.

The calls I'm getting have shifted from "help me advance" to "help me understand what's coming."

That shift tells me everything about where we are in late 2025.

You don't have to panic. But you do need to pay attention.

And you need to start asking yourself the questions that smart executives are already asking:

  • What roles actually survive this transformation?
  • How do I position myself as strategically valuable, not operationally redundant?
  • What's my backup plan if my current path doesn't work?
  • Am I willing to consider alternative models that provide more control?
  • Can I make an informed decision rather than hoping the wave passes?

The answer to those questions will determine how you navigate the next 2-3 years.

And whether you look back and realize you saw it coming—or wish you had.


Ready to Have This Conversation?

If this resonates and you want to explore what comes next—whether that's positioning yourself better in your current path or understanding alternative options—I can help.

This isn't about pushing you toward one solution. It's about helping you make an informed decision with complete clarity about the structural changes happening and the options available to you.

Book a Strategy Call to discuss your specific situation and what strategic positioning makes sense for you.

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Written by

Bill Heilmann