HGCPosts

A High-Growth CEO Perspective on the Transition to an AI Native Company

August 20, 2026
This post is part of our blog series examining the Ten CEO Roles through the...

The Race Towards AI Adoption. What Kind of “AI CEO Captain” Are You? Why Does it Matter?

May 12, 2026
Navigating AI requires close attention to FOUR of our TEN CEO Roles: Deliver Winning, Innovative...

How Successful CEOs Lead Today: The Ten Roles That Drive Alignment, Execution, and Sustainable Growth

March 1, 2026
The CEO role has always been demanding, but the expectations of today's leaders are fundamentally...

CEO Outlook 2025: Navigating Today’s Economic Climate with Resilience and Agility

October 22, 2025
CEOs currently need to lead through a lot of chaos and confusion. Rising costs, slower...

Building a Great Board Dynamic and Productive Board Meetings

April 14, 2023
Every CEO and their investors know how important this is.  In some companies, the relationship...

This post is part of our blog series examining the Ten CEO Roles through the lens of 30 years of experience working with high-tech, high-growth, investor-backed CEOs. Each post brings timely insights from our High-Growth CEO Forums®, Building the Profit Spiral® planning processes, CEO coaching and community conversations. Our previous post explored how leaders can bridge the gap between a personal CEO decision and organizational momentum. This post explores aspects of full AI-native transformation required to capture a premium valuation and build your competitive moat.

In a recent HGCEO cross-community online session, long-time member Gary Ambrosino, CEO of Ready Education, generously shared his ongoing experience and insights as he leads his company through an AI-native transformation. Regardless of where they sit on the AI adoption curve, our participating CEOs found immediate and actionable value in Gary’s insights.

What follows are examples of ongoing steps critical to make the transformation and takeaways from participants leaders must take to get there.  Thank you again Gary Ambrosino!

1. The CEO Must Lead the Transformation

  • The mandate to transition to AI cannot be delegated to your CTO. You must lead your team and your board through a series of strategic decisions that will fundamentally alter your value proposition, profitability, and valuation.
  • Your board and your executive team will often lack the in-depth knowledge required to advise you correctly on generative AI strategy.
  • Private equity investors may not know what to do, and venture capital investors simply want fast decision making. Waiting for consensus is not an option.
  • You must acquire a deep understanding of generative systems so you can make rapid decisions and lead from the front.

 

2. Valuation Follows AI Maturity

  • Buyers and investors are actively waiting for an AI unlock, and traditional SaaS company valuations are taking a hit. 
  • There are five levels of AI readiness, ranging from easily replaceable SaaS with low Alpha to fully AI-Native platforms. 
  • The difference in enterprise value between these tiers is massive. 
  • Companies that are merely “AI-Decorated” by adding a chatbot on top of old architecture might see a 1x to 2x revenue multiple, while true AI-Native companies built on modern AI stacks can command a 10x enterprise value.

 

3. Your AI Alpha Is Your Moat

  • The critical value question is not whether you are using AI to streamline basic operations. It is whether your AI strategy is built around what is unique about your company – this is your “AI Alpha.”
  • For a SaaS vendor, Alpha lives in the proprietary workflows, data signals, and processing rules refined through years of real customer usage and crystallized into your product structure.
  • AI is compelling because it unlocks this existing Alpha on an accelerated basis to add capabilities that were impossible before.
  • Encoding your Alpha into data sets, machine learning algorithms, and proprietary agents is the only thing competitors cannot replicate.

 

4. Understand Your Tokenomics and Take Action

  • Relying entirely on commercial hyperscaler platforms like OpenAI or Anthropic for your core product features creates a variable cost structure that can severely constrain your financial performance and erode gross margins. 
  • Gary uses the term “Tokenomics” to describe the critical management of these AI processing costs. 
  • By transitioning core workloads to self-hosted, open-weight models like Google Gemma on their own hardware, Ready Education was able to move from a variable, high cost of goods sold to a fixed SaaS annual subscription model, securing a 92.8 percent gross margin compared to just 14 percent on commercial APIs.

 

5. Incremental Updates Will Not Work

  • A real AI-native transformation requires a full re-platforming of the product, a complete culture shift to make operations “AI Fluid,” and a structured plan to sustain revenue growth during the transition. 
  • Modest, incremental updates are insufficient. 
  • To fund this transition at Ready Education, Gary ensured the company had the dedicated capital required to rebuild its data architecture from the ground up.

 

6. New Talent, Skills, and Learning Are Required

  • You must intentionally seed AI knowledge into your team. Gary introduced two critical new roles to ensure adoption moved safely and at speed. 
  • He hired an “AI Alchemist” who reports directly to the CEO, advising on strategic tech selection and building internal platforms. 
  • He also appointed a “Data Analyst” who controls and authenticates all data feeds, ensuring employees have a single, safe source of truth when building AI applications. 
  • Additionally, every employee is equipped with AI suites, and the entire engineering team is mandated to use Claude Code.

 

7. Re-Organize for Speed and Customer Responsiveness 

  • Traditional hierarchical structures move too slowly for the pace of AI innovation. 
  • Companies must flatten their organizations and reorganize for speed and communication. 
  • One of the most effective ways to accomplish this is by restructuring engineering departments into flexible, cross functional delivery pods. 
  • Under this model, engineers maintain a functional home for their craft, standards, and professional growth, but they deploy into specific, cross functional pods to execute deliverables. 
  • This dual structure allows the organization to dedicate a protected group to maintaining existing product revenue and keeping the lights on while the new delivery pods simultaneously build the AI native platform at an accelerated pace.

The top three actions for CEO’s to take right now:

  1. Uncover your company’s AI Alpha.
    What unique and valuable information do you have in your company’s data corpus and knowledge about your customer?Create a defensible competitive moat by building AI around that specific knowledge.
  2. Review the cost and build model.
    Evaluate open-source models, your token economics and your team structure to understand what it will cost to operate as an AI-native company without destroying your gross margins.
  3. Align your stakeholders.
    Your board, your investors, your executive team and your company must understand and align on what an AI-native transformation requires. This includes securing concrete agreement on the funding, divestitures, and team restructuring necessary to execute the transition.

The transition from legacy software to a fully AI native platform is no longer a future theoretical exercise. It is a present day mandate for protecting and multiplying your enterprise value. 

Incremental updates and simply decorating your current product with basic chat interfaces will not build a durable competitive moat. 

By stepping to the front to lead, identifying your unique AI Alpha, rigorously managing your tokenomics, and flattening your organization into agile delivery pods, you can separate your company from the pack and capture a premium valuation. 

The window for this transformation is actively closing, and the leaders who take decisive action right now will be the ones who secure their market position and drive sustained growth for the future.

Connect With Us…

To learn how we support CEOs directly and through investor portfolio services:

  • High-Growth CEO Forum®
  • High-Growth CEO Coaching™
  • Planning for Growth™ — Building the Profit Spiral®
  • Building the Executive Team as Leaders of Growth®
  • CEO Workshops
  • Investor & Incubator Programs/Workshops

Visit High-Growth CEO to learn more.

This is the first in our blog series examining the Ten CEO Roles through the lens of 30 years of experience working with high-tech, high-growth, investor-backed CEOs. Each post will bring timely insights from our High-Growth CEO Forums® (HGCFs), Building the Profit Spiral® planning processes, and CEO coaching. Through our Ten CEO Roles Survey, found at the end of every post, we invite you to share your current experiences which will be rolled into an anonymous update on a regular basis. Thank you for participating in our High-Growth CEO conversation!

How Successful CEOs Lead Today: The Ten Roles That Drive Alignment, Execution, and Sustainable Growth

The CEO role has always been demanding, but today’s expectations of today’s leaders are fundamentally different. Investor-backed CEOs are being asked to operate at multiple altitudes at once, navigate constant change, and lead organizations that are growing, transforming, and stretching faster than ever before. At the same time, they are expected to stay grounded, think clearly, build aligned teams, and make high-quality decisions with imperfect information.

One theme has become unmistakable. Great CEOs are not defined by personal heroics or sheer effort. They are defined by how well they understand and execute the core responsibilities of the role. These responsibilities are predictable, learnable, and repeatable. When leaders master them, companies accelerate. When leaders neglect them, growth becomes harder, execution becomes inconsistent, and complexity starts to win.

The High-Growth CEO Roles Framework (HGCRF) outlines the essential responsibilities every CEO must understand to lead a company through the Predictable Stages of Corporate Growth®.

The HGCRF applies whether you are a first-time founder or a multi-time CEO, and whether your company is expanding, transforming, or navigating turbulence.

 

The Ten CEO Roles Framework:

Over the course of this blog series we will explore each of the ten CEO roles and bring synthesized insights from the front lines of our client engagement. What we are seeing, what is working, and how difficult decisions are being made.

We are also asking you to weigh in. Which of these roles is requiring your most urgent attention right now? What is the one question you need answered to move forward? The pulse of what CEOs are experiencing in the real world is exactly what shapes this series, and your perspective matters.

One. You: Focus on your health and wellbeing. Embrace learning and role evolution

Two. Values: Live your core leadership principles. Serve as chief of culture, communication, and organization

Three. Customer/Product: Deliver winning, innovative, timely products and relevant services to carefully selected customers and markets — with increasingly predictable revenue results over time

Four. Team: Continuously evolve a high-performing executive team — mentoring, hiring and firing with appropriate timing related to company growth stage

Five. Alignment: Deliver your mission/core purpose and two- to three-year envisioned future state

Six. Execution: Ensure delivery of a shared multi-year company roadmap by developing, evolving and leading an annual operating system

Seven. Resource Stewardship: Fundraise for growth and/or build EBITDA. Never run out of cash

Eight. Transformation: Lead the company through change and transformation

Nine. Board: Manage the board of directors — investors, independents and other advisors

Ten. Market Ecosystem: Connect with CEOs of potential strategic partners and acquirers — years ahead of a potential tangible outcome

Use the HGCRF to Navigate Success!

The environment CEOs are operating in now is evolving at lightning speed. Markets move faster. AI is changing the game. Teams expect and need more clarity, transparency, and alignment. Execution requires cross-functional coordination. Technology is reshaping how organizations operate. And the emotional demands of the role have never been higher.

When CEOs effectively deliver on the HGCRF they:

  • Approach their role with structure
  • Treat leadership as a discipline imbued with their core values
  • Understand where to spend their time, how to elevate their thinking, and how to create alignment across the organization
  • Know which responsibilities belong to them and which belong to their team and how those responsibilities need to evolve
  • Lead from steadiness, not strain
  • Create stronger alignment, better decision-making, healthier executive teams, and a more resilient organization

As one of our clients states: “When I understand the role I need to play, everything else becomes easier. My team moves faster, decisions get clearer, and the company feels more aligned.”  

We Believe…

Great CEOs are not born. They develop through intention, reflection, practice, structure, and learning. They evolve to support the evolution of their companies. They learn to lead. Not by doing more, but by doing the right things at the right altitude.

These ten roles provide a foundation for clarity, focus, and high-impact leadership in a world where the demands on CEOs continue to grow.

Right now the top two critical roles identified by our clients are: 

  • Delivering winning, innovative and TIMELY products
  • Stewarding resources carefully

In subsequent posts we will apply learnings and discoveries about how to address current CEO challenges in executing these ten areas successfully.

Which two roles are most important for you to focus on right now? What is the one thing you need to do differently, or the one action you need to take to be most effective in those areas? Take a minute to weigh in below. 

Connect With Us…

To learn how we support CEOs directly and through investor portfolio services:

  • High-Growth CEO Forum®
  • High-Growth CEO Coaching™
  • Planning for Growth™ — Building the Profit Spiral®
  • Building the Executive Team as Leaders of Growth®
  • CEO Workshops
  • Investor & Incubator Programs/Workshops

Visit High-Growth CEO to learn more.


CEOs currently need to lead through a lot of chaos and confusion. Rising costs, slower customer decisions, and geopolitical uncertainty are creating real challenges. At the same time, rapid AI adoption is opening both new opportunities and fast growing competitive threats across market and fundraising landscapes.

To better understand how companies are experiencing and navigating these conditions, we asked CEOs in our High-Growth CEO Forums (HGCFs)  to share their recent reflections. Their perspectives, drawn from candid peer discussions, reveal a mix of resilience, cautious optimism, and sharpened focus on strategic priorities.

“Nearly half of CEOs reported no material change in recent revenue performance, while a quarter saw moderate declines.”

 

CEO Perspectives on Recent Performance

When asked how revenue and closed-won performance compared to forecast, CEOs reported a wide range of outcomes. Nearly half said they experienced little or no material change, a signal that steady demand and strong pipeline conversion remain possible in today’s market. At the same time, one in four experienced moderate declines, citing rising costs, delayed customer approvals, and shifting internal priorities as key reasons. A smaller, but significant, group reported major declines of 30 percent or more. For these CEOs, volatility is very real and often outside their direct control.

The qualitative reflections behind the numbers add important context. As one CEO put it, “The appetite is there, the approvals are just slower.” Another explained, “Internal bandwidth is now one of our biggest bottlenecks.” These perspectives underscore that while many CEOs are holding ground, others are fighting uphill battles against forces that include both market dynamics and internal constraints.

 

CEO Outlook for the Months Ahead

Looking forward, CEOs are preparing for the remainder of 2025 with a pragmatic lens. Roughly 40 percent expect no material change from their original forecasts, which suggests confidence in their positioning and resilience in their industries. Another 40 percent expect performance to be down between 5 and 20 percent, reflecting continued caution and a recognition that external conditions may weaken pipelines even if demand holds. A smaller group anticipates sharper declines of more than 20 percent and are bracing their companies for more aggressive cost discipline.

To illustrate this, the survey data shows a nearly even split: 40 percent holding steady, 40 percent expecting modest declines, and 20 percent bracing for significant headwinds.

“CEO outlook for the remainder of 2025 reflects pragmatism: 40% expect steady performance, while another 40% anticipate modest declines.”

The underlying rationale for these expectations offers deeper insight. When asked what is driving this outlook, two factors stood out:

  1. Internal resourcing and bandwidth – CEOs are prioritizing where to place limited time and capital, often delaying lower-priority initiatives.
  2. Budget freezes and extended approvals – Even when appetite exists, approvals are slower, requiring CEOs to manage pipeline health more closely.

Together, these accounted for the majority of slowdown reasons cited.

“Budget freezes and internal bandwidth constraints were cited most often as reasons for slower cycles.”

Not every outlook was defensive. Several CEOs emphasized that technology, particularly AI, is creating measurable offsets. One remarked, “AI-driven efficiencies allowed our teams to close deals faster than expected,” illustrating how innovation is helping companies protect momentum even as macro conditions drag.

 

 

What is Driving Slowdowns?

When CEOs described what is slowing execution, three factors emerged most frequently. 

  1. Roughly 35 percent pointed to budget freezes as the leading barrier, noting that even well-qualified opportunities are being delayed until spending restrictions ease. 
  2. About a quarter highlighted extended approval cycles, with decisions getting caught in additional layers of review or, as one CEO described, “stuck in committee.” 
  3. Another 20 percent pointed to internal bandwidth constraints, acknowledging that stretched teams are forcing leaders to prioritize only the initiatives most critical to near-term growth. 

Taken together, these factors explain why even companies with strong pipelines are experiencing slower-than-expected sales cycles. As one CEO summarized, “We are still seeing opportunities, but the pace of execution is constrained in ways we have not experienced before.”

 

Where CEOs See Opportunities

Despite headwinds, CEOs are not standing still. Instead, they are identifying levers that create advantage in this environment. 

  1. AI adoption is leading the way. What was once experimental is now mainstream, and CEOs are reporting tangible results in shortened sales cycles, improved forecasting, and measurable efficiency gains across the organization. 
  2. Selective investment is another clear trend. CEOs are concentrating capital and talent on opportunities with the highest likelihood of revenue conversion, often shelving or delaying initiatives that do not have a clear payoff. 
  3. Finally, resilient sectors continue to stand out. Companies with strong product-market fit are maintaining momentum, and CEOs in these industries are leaning into customer demand to reinforce their position.

AI in particular is no longer optional. It is reshaping sales cycles and execution across industries, and the efficiency gains are proving too material to ignore. The broader theme is that even in a challenging climate, CEOs are finding ways to convert disruption into leverage. Those who can integrate AI, allocate capital with discipline, and double down on proven markets are positioned not just to survive but to gain ground.

 

What This Means for CEOs Right Now

The findings confirm what most CEOs are already living every day: leading a company in 2025 requires both confidence and caution. The CEOs who are thriving are those who stay agile, revisit pipeline health often, and leverage tools like AI to sharpen efficiency and execution. Just as importantly, they are communicating transparently to their Boards, investors, and employees about the realities of the environment.

The CEO role has always demanded resilience. In today’s climate, it demands even more discipline, speed of adjustment, the ability to find growth in unexpected places, and the capacity to lead the company through uncharted waters.

 

Share Your Perspective

The insights we have gathered reflect how some CEOs in our High-Growth CEO Forums are navigating today’s complex business climate. We now want to broaden the lens. We invite you to add your perspective through our short CEO Outlook Survey. It takes only a few minutes, is completely anonymous, and will remain open until October 30.

We will publish the aggregated results on LinkedIn in early November so you can compare your outlook with that of your peers.

👉 Take the CEO Outlook Survey

Every CEO and their investors know how important this is.  In some companies, the relationship between CEO and Board is a model of trust, efficiency, and focus on critical growth issues. In other companies, CEOs and their Boards unfortunately seem to thrash around and struggle to find the right dynamic.
Building a great board dynamic is not exclusively about board meetings.  Good relationship-building takes place with 1:1 connections. But the primary and official vehicle are your formal board meetings. CEOs need to be on top of their game in this arena. In our High-Growth CEO Peer Forums, this CEO Member Challenge comes up frequently, in various flavors and forms. Here is some guidance from HGCF members for creating and delivering great Board meetings and relationships.
ESTABLISH CLARITY– Be very clear on the essential role of everyone in the room:
  1. Board: financial investment, governance, compensation, pattern detection, selective input on the right strategic topics, help with fundraising, hiring, connections to partners
  2. CEO and Leadership Team: forecast, execute, report results, give customer/ market/competitive flavor, frame the right key issues, lead the discussion on recommendations and solutions
  3. Make sure critical Board roles are in place – don’t forget to fill the independent seat(s) and the compensation committee
CREATE CONSISTENCY – Have a standard approach, rhythm, and template:
  1. Create the appropriate cadence (maximum of monthly, minimum of quarterly) and calendar the meetings at the beginning of each fiscal year
  2. Send materials ahead of time
  3. At every meeting review financials, emphasize key sales updates and product development highlights
  4. Hand-pick and frame 1-3 key topics for each meeting for carefully structured Board input. Focus the presentation on just these items (put all the rest in a back-up appendix)
STAY FOCUSED – The CEO sets the expectations, tone and frames the discussion:
  1. Avoid the dreaded free-for-all by staying laser focused on the discussion at hand.  Do not get side-tracked. Boards will talk and opine on anything… but their role is to approve (or not)
  2. Don’t get trapped into making decisions at the Board meeting if it’s not warranted.  It’s perfectly reasonable to say “we acknowledge and appreciate the input…we’ll work on it and get back to you” and then make a point of doing exactly that
  3. Help the Board help you by giving them meaningful projects and leveraging their expertise.
BUILD TRUST & TRANSPARENCY: Be extra, extra careful about setting the Board’s expectations about revenue and other critical metrics. Missing the plan of record erodes investor confidence quickly and missing it repeatedly can lead to a CEO change:
  1. Remember, the CEO knows the company better than anyone else so don’t agree to plans you don’t believe in – even if you feel pressured to do so
  2. Sometimes CEOs need to temper their own optimism to avoid adopting hopeful versus realistic, negative scenario tested plans
  3. When big macro trends like pandemics, recessions, wars and bank meltdowns cause unforeseeable disruptions, or other major negative forces appear, CEOs should change the plan asap with feedback from the Board
  4. Be precise about communicating revenue or growth that is one-off and not repeatable, or a result of timing quirks. Otherwise you’ll be explaining these endlessly in the future.
  5. Early stage companies should understand, share and measure the metrics that indicate successful progress and learning – which may not be revenue
CREATE TEAM VISIBILITY & ACCOUNTABILITY: Involve your key team members in Board meetings where and when appropriate:
  1. It gives the Board visibility into your team
  2. It’s good team member development, recognition, and importantly adds to their personal accountability
  3. Coach your team members to help them develop their Board presentation skills. Be crystal clear about their role in the meeting. Make sure they understand how to manage Board questions, and how to keep their input focused and aligned with the company’s goals
NO SURPRISES – EVER! Do not wait for the regularly scheduled Board meeting to share bad news – communicate it at once. Good news should travel fast, but bad news should travel faster!