What Got You Here Won’t Keep You Here: A Letter to Technology Executives

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I wrote recently about how mid and late-career developers, engineering directors, and VPs of engineering need to rebuild around AI. This is the version for CxOs. Because leading a company through AI transformation is an order of magnitude harder than transforming engineering organizations, and the competition for board seats in 2028 will be brutal.

You’ve worked twenty, twenty-five, maybe thirty years to get here. You’re good at running organizations. You’ve earned your position. I’m writing this because what I’m seeing across the industry needs to be said directly.

The path that made you a successful executive won’t make you someone boards want. The executives who understand this in 2025 will have board seats and top-tier opportunities in 2028. The ones who don’t will be explaining in interviews why their companies fell behind while their peers built sustainable competitive advantages.

The Reality Right Now

Organizations have rolled out AI coding agents and are watching which companies drive transformational competitive advantage and which fall behind. Most organizations are going all-in on AI. The ones that aren’t will be case studies in failure to adapt.

If you’re at a pure software company (SaaS, platforms, developer tools), you have 12 to 18 months before the market starts separating winners from losers.

If software supports a physical product or service (manufacturing, healthcare, logistics), you have three to five years. But the gap between companies transforming now and companies waiting is widening every quarter.

The Market Truth Nobody’s Saying

Right now, boards can’t hire executives with three years of AI transformation experience at scale because those executives barely exist yet.

In 2028, they will exist.

When that board is looking for their next CTO, CEO, or board member, are you the executive with the proven transformation track record, or the person being passed over for someone who has it?

This isn’t about job security. This is about being positioned for board seats, advisory roles, or your next executive opportunity in 2028. About having a legacy that opens doors instead of raising questions about why you didn’t see this coming.

Why This Is Hard for CxOs

VPs need to prove they can transform engineering organizations. You need to prove you can transform entire companies.

Those aren’t the same skill set.

VPs navigate organizational politics across hundreds of people and build governance at scale. You need to reshape entire companies, manage boards through transformation, navigate regulatory concerns, explain business model implications to investors, and build sustainable competitive advantages that show up in market position.

You need to understand the technology deeply enough to make strategic decisions AND navigate the complexity of getting boards, investors, regulators, and thousands of employees aligned.

The executives who succeed won’t be the ones who hired consultants and rolled out AI tools. They’ll be the ones who led companies through transformation and can prove it with competitive advantages that show up in the market.

What Your 2028 Legacy Needs

In 2028, when you’re being recruited for board positions or your next executive role, they’ll ask: “How did your organization adapt to AI? What was your strategy? What business outcomes did you achieve?”

Your competition will talk about leading companies through fundamental transformation. Avoiding hundreds of new hires because teams built AI systems to handle that work. Reducing cost of goods sold by 50% across the organization, increasing flow by 60%, improving time-to-market by 45%. They’ll describe restructuring entire companies for AI-enabled work. They’ll explain governance frameworks that satisfy board-level scrutiny and regulatory requirements. They’ll show competitive advantages in cost structure and speed that win deals they couldn’t compete for before.

Will you have those stories? Or will you say “We adopted tools and hired consultants”?

The Five Capabilities You Need to Build

Build Deep Strategic Understanding

You need to understand the business model implications. What does it mean when work that used to take three months takes three weeks? How does that change your competitive position? Your cost structure? Your talent strategy?

You can’t answer these questions from executive summaries. You need enough understanding of how AI agents work, how teams build systems with them, how to orchestrate them, to make informed strategic decisions.

This isn’t about writing code. It’s about understanding the technology well enough to drive strategy, evaluate what your organization tells you, and explain it to boards and stakeholders credibly. The discomfort you feel getting technical again is the skill building. That’s how you know it’s working.

Reshape the Entire Organization

Transform the entire company. Don’t just flatten—rethink career paths, compensation models, hiring profiles, organizational design from first principles.

Figure out what “senior engineer” means when a 25-year-old who’s great with agents outproduces a 20-year veteran who isn’t. Navigate the board conversation about why your engineering headcount isn’t growing even though output is.

Build competitive advantage through organizational design. The organizations you’ll lead past 2028 will not look like they do today. Flatter. Faster. More leveraged. Different capabilities valued. Figure out what that looks like at scale and make it real.

Build Enterprise Governance at Scale

Build governance that works across thousands of people and satisfies board-level scrutiny. Navigate regulatory concerns. Establish the risk framework for AI agents throughout the development lifecycle and in production systems.

Build the compliance story. Create the governance model for agent orchestration and AI systems in the SDLC that becomes industry best practice. Other companies will study what you built.

Don’t delegate this. Own it at the executive level because the board needs to understand and approve the risk framework. The executives who can demonstrate they navigated this complexity successfully—who can show they built governance that satisfied boards and regulators—those are the executives who get board seats.

Master Board and Stakeholder Management

Manage board concerns about AI risk and opportunity. Explain to investors why your cost structure is changing. Navigate competitive pressure without creating panic.

Build the narrative that makes the transformation make sense to non-technical stakeholders. Be the person who can walk into any room—board, customers, regulators, investors—and explain what you’re doing and why it’s responsible.

Manage expectations while driving urgency. Build confidence while acknowledging risk. This is executive leadership at the highest level.

Build Capability Development Into Organizational DNA

Build systems that develop capability in thousands of people. Change hiring profiles. Rethink onboarding. Make “builds AI systems” and “orchestrates agents” core competencies across your entire organization.

Create the talent pipeline that sustains your competitive advantage. Build capability development systems that make transformation sustainable, not dependent on a few key people.

Measure this as a strategic capability, not a training program. Have metrics showing that capability development drives competitive advantage.

The Timeline Reality

You have three years to build this transformation legacy.

Executives who started a year ago already have compelling stories. They can talk about leading companies through transformation. They can show business outcomes: “We reduced cost of goods sold by 50% across the organization and increased flow by 60%. We’re winning deals on speed and price that we couldn’t compete for before.”

Executives who start today will have solid track records by late 2026. They’ll have transformed entire companies. They’ll understand what governance satisfies boards and regulators from real implementation. They’ll have relationships with boards and stakeholders built over time.

Executives who wait another year will be competing in 2028 against candidates with three years of demonstrated success leading companies through transformation, building sustainable competitive advantages, navigating complex stakeholder landscapes, and creating transformational business outcomes.

What Success Looks Like

By 2028, you should be able to walk into any board room and tell stories like:

“I led a company through complete transformation. We avoided needing to hire hundreds of additional people because our teams built AI systems to handle that work. Cost of goods sold dropped 50% across the organization. Flow increased 60%. Time-to-market improved 45%. These outcomes created sustainable competitive advantage—we’re winning deals on speed and price that we couldn’t compete for two years ago.”

“I restructured the entire organization for AI-enabled work. We went from traditional hierarchies to flatter structures that empower people. Our engagement scores increased while productivity increased. I learned what organizational shape works at scale when AI agents change economics, and I built it.”

“I built enterprise governance that works across thousands of people and satisfies board-level scrutiny. Legal is comfortable. Security is comfortable. Regulators understand our framework. The board approved our risk model. I navigated all of these stakeholders successfully while enabling speed.”

“I managed the board through this transformation. I explained the business model implications. I navigated concerns about risk. I built confidence while maintaining urgency. The board understands what we’re doing and why, and they’re supportive because I brought them along throughout.”

“I built capability development into our organizational DNA. We hire for AI capability. We develop it systematically. We measure it as a competitive advantage. Our talent pipeline sustains our advantage—this isn’t dependent on consultants or a few key people.”

These are the stories that get you board seats. These are the capabilities that position you for top-tier opportunities. This is what makes you the executive that other companies want to recruit or learn from.

Your Legacy Starts Today

The market in 2028 will have executives with proven transformation track records at scale. Executives who can walk into board rooms with complete stories about leading companies through AI transformation, building sustainable competitive advantages, navigating complex stakeholder landscapes, and creating transformational business outcomes.

Those executives will get the opportunities—the board seats, the advisory roles, the top-tier executive positions at the companies you actually want to work for.

You can be one of those people. But you need to start building that track record today, while you can learn through doing at your current company, so you have it when you’re competing for opportunities against executives who already spent three years building theirs.

You can do this. The capabilities are learnable. The path is clear enough if you start walking it.

Start today. Where you are three years from now—what opportunities you have, what boards want you, what your legacy looks like—depends on what you do in the next three years.

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