I wrote recently about how mid and late-career developers and engineering directors need to rebuild around AI. This is the version for Vice Presidents. Because transforming two hundred person engineering organizations is an order of magnitude harder than transforming teams, and the competition for Chief Technology Officer roles in twenty twenty-eight will be brutal.
You have worked fifteen, twenty, maybe twenty-five years to get here. You are good at running engineering organizations. You have earned your position. I am writing this because what I am seeing across the industry needs to be said directly.
The path that made you a successful Vice President will not make you a successful Chief Technology Officer. The Vice Presidents who understand this in twenty twenty-five will be Chief Technology Officers in twenty twenty-eight. The ones who do not will be explaining in interviews why their organizations stayed flat while their peers delivered transformational business outcomes.
Look. The reality right now is that 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 are not will not help you remain relevant in twenty twenty-eight.
If you are at a pure software company, like a Software as a Service platform or a developer tools firm, you have twelve to eighteen months before patterns become clear and start driving C-suite hiring decisions.
If software supports a physical product or service, like manufacturing, healthcare, or logistics, you have three to five years. But the gap between Vice Presidents building transformation experience now and those waiting is widening every quarter.
Here is the market truth nobody is saying. Right now, companies cannot hire Vice Presidents with three years of AI transformation experience at scale because those people barely exist yet.
In twenty twenty-eight, they will exist.
When that company is looking for their next Chief Technology Officer, are you the Vice President with the proven transformation track record at two hundred people, or the person being passed over for someone who has it?
This is not about job security. This is about being positioned for Chief Technology Officer roles, Chief Executive Officer opportunities, or board seats in twenty twenty-eight. It is about having a resume that opens doors instead of raising questions about why you did not adapt.
Now, you need to understand why this is hard for Vice Presidents. Directors need to prove they can transform teams. You need to prove you can transform entire engineering organizations.
Those are not the same skill set.
Directors navigate team-level politics and build governance for twenty to forty people. You need to navigate organizational politics across hundreds of people. You have to get legal, security, compliance, and boards comfortable with AI. You need to build governance frameworks that work across multiple teams with different technology 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. That includes engineering, legal, security, compliance, finance, the C-suite, and the board.
The Vice Presidents who succeed will not be the ones who rolled out AI tools. They will be the ones who transformed how hundreds of people work and can prove it with transformational business outcomes.
Consider what your twenty twenty-eight Chief Technology Officer resume needs. In twenty twenty-eight, when you are being recruited for top roles, they will 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 two hundred person engineering organizations. They will cite reducing cost of goods sold by fifty percent, increasing flow by sixty percent, and cutting time-to-market by forty percent. They will describe restructuring from six management layers down to four with people thriving. They will explain governance frameworks that work across the entire organization. They will show the playbook other Vice Presidents want to copy.
Will you have those stories? Or will you say, we adopted tools and saw some improvements?
So, here are the five capabilities you need to build. First, you must build a deep technical understanding. You need enough hands-on understanding to evaluate what your directors are telling you. You must be able to distinguish between, this does not work, and, we have not figured out how to make this work yet.
You need to understand how AI agents work, how to orchestrate them, and 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 is not about writing code daily. It is about maintaining enough technical engagement to lead a technical transformation credibly. The discomfort you feel getting technical again is the skill building. That is how you know it is working.
Second, you need to reshape organizations at scale. Prove organizational redesign works at one hundred to three hundred 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. Do not theorize. Do it and measure the results. The Vice Presidents who can demonstrate they actually did this work at scale are the ones companies want as Chief Technology Officers.
Third, build governance frameworks at scale. Build governance that works across multiple teams with different technology 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, and 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.
Fourth, you must master organizational buy-in at scale. This is where most Vice Presidents fail. You must navigate organizational politics across hundreds of people. Get multiple stakeholders aligned. That includes engineering, legal, security, compliance, finance, the C-suite, and the 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 Vice Presidents who can demonstrate they navigated this complexity successfully, those who can show they built organizational buy-in across multiple stakeholders, those are the people who get Chief Technology Officer offers.
Fifth, 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, and governing AI in the Software Development Life Cycle.
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.
Look. Here is the timeline reality. You have two years to build this transformation story.
Vice Presidents who started a year ago already have compelling stories. They can talk about transforming one hundred fifty person organizations. They can show business outcomes. For example, they reduced cost of goods sold by fifty percent and increased flow by sixty percent.
Vice Presidents who start today will have solid track records by late twenty twenty-six. They will have transformed entire organizations. They will understand what governance actually works at scale from real implementation. They will have relationships with legal, security, and boards built over time.
Vice Presidents who wait another year will be competing in twenty twenty-eight 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.
Let us look at what success looks like. By twenty twenty-eight, you should be able to walk into any Chief Technology Officer interview and tell stories.
I transformed a two hundred person engineering organization. Cost of goods sold dropped fifty percent and flow increased sixty percent. We cut time-to-market by forty percent. These are not projections. These are measured outcomes over eighteen months.
I restructured the organization from six management layers to four. People have more ownership and autonomy. Our engagement scores increased while we are 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, and govern AI in the Software Development Life Cycle. 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 have 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 Chief Technology Officer roles. These are the capabilities that position you for Chief Executive Officer opportunities or board seats.
Your career in twenty twenty-eight starts today. The market in twenty twenty-eight will have Vice Presidents with proven transformation track records at scale. People who can walk into 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.
Right. Those Vice Presidents will get the opportunities. The Chief Technology Officer roles, the Chief Executive Officer positions, and 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 are competing against peers who already spent two years building theirs.
Here is the thing. 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, and what your trajectory looks like, depends on what you do in the next two years.