What Got You Here Won’t Keep You Here: A Letter to VPs of Engineering

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I wrote recently about how mid and late-career developers and engineering directors need to rebuild around AI. This is the version for VPs. Because transforming 200-person engineering organizations is an order of magnitude harder than transforming teams, and the competition for CTO roles in 2028 will be brutal.

You’ve worked fifteen, twenty, maybe twenty-five years to get here. You’re good at running engineering 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 VP won’t make you a successful CTO. The VPs who understand this in 2025 will be CTOs in 2028. The ones who don’t will be explaining in interviews why their organizations stayed flat while their peers delivered transformational business outcomes.

The Reality Right Now

Organizations have rolled out AI coding agents and are watching which engineering organizations drive dramatic business improvements and which stay flat. Most organizations are going all-in on AI. The ones that aren’t won’t help you remain relevant in 2028.

If you’re at a pure software company (SaaS, platforms, developer tools), you have 12 to 18 months before patterns become clear and start driving C-suite hiring decisions.

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

The Market Truth Nobody’s Saying

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

In 2028, they will exist.

When that company is looking for their next CTO, are you the VP with the proven transformation track record at 200 people, or the person being passed over for someone who has it?

This isn’t about job security. This is about being positioned for CTO roles, CEO opportunities, or board seats in 2028. About having a resume that opens doors instead of raising questions about why you didn’t adapt.

Why This Is Hard for VPs

Directors need to prove they can transform teams. You need to prove you can transform entire engineering organizations.

Those aren’t the same skill set.

Directors navigate team-level politics and build governance for 20 to 40 people. You need to navigate organizational politics across hundreds of people, get legal and security and compliance and boards comfortable with AI, and build governance frameworks that work across multiple teams with different tech stacks and risk profiles.

You need to understand the technology deeply enough to evaluate what your directors are telling you AND navigate the complexity of getting multiple stakeholders aligned—engineering, legal, security, compliance, finance, C-suite, board.

The VPs who succeed won’t be the ones who rolled out AI tools. They’ll be the ones who transformed how hundreds of people work and can prove it with transformational business outcomes.

What Your 2028 CTO Resume Needs

In 2028, when you’re being recruited for CTO roles, they’ll ask: “How did you transform your engineering organization for the AI era? What business outcomes did you achieve at scale?”

Your competition will talk about transforming 200-person engineering organizations. Reducing cost of goods sold by 50%, increasing flow by 60%, cutting time-to-market by 40%. They’ll describe restructuring from six management layers to four with people thriving. They’ll explain governance frameworks that work across the entire organization. They’ll show you the playbook other VPs want to copy.

Will you have those stories? Or will you say “We adopted tools and saw some improvements”?

The Five Capabilities You Need to Build

Build Deep Technical Understanding

You need enough hands-on understanding to evaluate what your directors are telling you. To distinguish between “this doesn’t work” and “we haven’t figured out how to make this work yet.”

You need to understand how AI agents work, how to orchestrate them, how to build systems with them. Ask the right questions in architecture reviews. Know when a director is giving you excuses versus legitimate technical barriers.

This isn’t about writing code daily. It’s about maintaining enough technical engagement to lead a technical transformation credibly. The discomfort you feel getting technical again is the skill building. That’s how you know it’s working.

Reshape Organizations at Scale

Prove organizational redesign works at 100 to 300 people. Go from six management layers to four and show people are thriving with more ownership. Figure out how to coordinate multiple teams building AI systems that orchestrate together.

Learn which governance decisions need to be centralized and which should be team-level. Figure out what “senior engineer” means when capability with AI agents matters more than years of experience.

Build the playbook for organizational design at scale that actually works in practice. Don’t theorize—do it and measure the results. The VPs who can demonstrate they actually did this work at scale are the VPs companies want as CTOs.

Build Governance Frameworks at Scale

Build governance that works across multiple teams with different tech stacks and risk profiles. Standardize what needs to be standard and leave flexibility where it matters.

Build the security review process for AI agents in production. Create training programs that teach agent governance at scale. Establish how to test AI-enabled systems, review agent-generated code, handle agent orchestration in production environments.

Be the person who got legal and security to yes in six weeks while other companies spent six months in analysis paralysis. Have the playbook for navigating these conversations at scale.

Master Organizational Buy-In at Scale

This is where most VPs fail. Navigate organizational politics across hundreds of people. Get multiple stakeholders aligned—engineering, legal, security, compliance, finance, C-suite, board.

Build the business case that gets finance comfortable with the investment. Manage up to the C-suite and down to your directors. Be the translator between engineering reality and executive concerns.

Know how to say “we need to move fast on AI” in a way that legal and security can support rather than block. Build the relationships and trust that enable speed. The VPs who can demonstrate they navigated this complexity successfully—who can show they built organizational buy-in across multiple stakeholders—those are the VPs who get CTO offers.

Develop Capability at Scale

Build capability development programs that work across hundreds of people. Create training that actually transfers skills for building AI systems, orchestrating agents, governing AI in the SDLC.

Build communities of practice. Figure out how to scale the learning from your best teams to your struggling teams. Measure capability development as a business outcome, not just a training metric.

Identify which teams have strong capability and which are struggling. Have programs to develop capability systematically. Have metrics showing that capability development drives business outcomes.

The Timeline Reality

You have two years to build this transformation story.

VPs who started a year ago already have compelling stories. They can talk about transforming 150-person organizations. They can show business outcomes: “We reduced cost of goods sold by 50% and increased flow by 60%.”

VPs who start today will have solid track records by late 2026. They’ll have transformed entire organizations. They’ll understand what governance actually works at scale from real implementation. They’ll have relationships with legal, security, and boards built over time.

VPs who wait another year will be competing in 2028 against candidates with three years of demonstrated success transforming organizations at scale, building governance that works, navigating complex stakeholder landscapes, and driving transformational business outcomes.

What Success Looks Like

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

“I transformed a 200-person engineering organization. Cost of goods sold dropped 50% and flow increased 60%. We cut time-to-market by 40%. These aren’t projections—these are measured outcomes over 18 months.”

“I restructured the organization from six management layers to four. People have more ownership and autonomy. Our engagement scores increased while we’re shipping faster. I learned what organizational shape works when AI agents amplify capability, and I have the playbook to do it again.”

“I built governance frameworks that work across the entire engineering organization. Every team understands how to build AI systems safely, orchestrate agents, govern AI in the SDLC. Legal and security are comfortable because I built frameworks that enable speed while managing risk.”

“I navigated the organizational complexity of transformation at scale. I got legal to yes. I got security to yes. I got compliance comfortable. I brought the board along. I know how to have these conversations because I’ve had them successfully across multiple stakeholders.”

“I developed capability in hundreds of engineers. I built programs that work. I can show you the before and after metrics. Capability development became a competitive advantage because I made it systematic.”

These are the stories that get you CTO roles. These are the capabilities that position you for CEO opportunities or board seats.

Your Career in 2028 Starts Today

The market in 2028 will have VPs with proven transformation track records at scale. VPs who can walk into CTO interviews with complete stories about reshaping organizations, building governance at scale, navigating complex stakeholder landscapes, developing capability across hundreds of people, and driving transformational business outcomes.

Those VPs will get the opportunities—the CTO roles, the CEO positions, the board seats 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 companies still develop people internally, so you have it when the market has options and you’re competing against VPs who already spent two 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 companies want to hire you, what your trajectory looks like—depends on what you do in the next two years.

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