An Invitation for CEOs & Senior Leaders

Lead Confidently
Through the AI Era

A peer board, a personal AI operating system, and team-wide capability — delivered on a predictable monthly rhythm. Not a course. Not a tool. An installed operating system for how you lead.

Book Your 30-Min Discovery Call Attend a Free Session

Curated cohort of 8–12 CEOs · Limited seats by design

What is Leading in the AI Era?

Leading in the AI Era is a monthly CEO Executive Peer Board for founders and senior leaders at $5M–$100M organizations. Each month, members attend a real-time learning session that unlocks productivity immediately, deploy what they learned inside their business, and return to share results with a curated cohort of non-competing CEOs. It combines a personal 1:1 AI Operating System install, monthly coaching, and team-wide capability through the Humans + Agents platform — all on a predictable monthly rhythm with monthly check-ins and a full quarterly roundtable. Facilitated by Laura Ali and Maureen Ennis.

8–12CEOs per Cohort
10Functional Systems Installed
30 DaysTo Your AI Operating System
90 DaysTo Measurable Team Adoption

Where Most Leaders Get Stuck

CEOs who want to lead with AI are stuck in one of three places — and none of them lead to results.

📱

Dabbling without a system

Using ChatGPT on the phone here and there — but without a real operating system, it doesn't compound into anything meaningful.

🛠️

Buying tools teams don't adopt

Investing in AI tools that look great in demos but sit unused. The gap between tool and transformation doesn't close on its own.

👀

Watching competitors pull ahead

Knowing AI will change everything but not knowing what to copy, what to trust, or how to operationalize it across the organization.

They need three things at once: a way to personally lead with AI, a working system for their own day-to-day, and a way to spread that capability across their organization. This offer delivers all three.

Four Components. One Relationship.

Every month, you leave with an upgrade running in your business — real-time learning sessions that unlock productivity immediately, backed by peer accountability and 1:1 coaching.

01
Monthly Check-In + Full Quarterly Roundtable

Monthly Executive Peer Board

A curated cohort of 8–12 CEOs who meet for monthly check-ins to share AI challenges, wins, and working solutions — plus a full quarterly roundtable for deeper strategic work. Facilitated by Laura and Maureen. Structured agenda, confidential, peer-to-peer accountability. The outcome standard: every session ends with something installed in your business, not just discussed.

02
90 Min Kickoff + Monthly Install Cadence

1:1 AI Operating System Install

A dedicated onboarding session to install your personal file operating system, wire up your Chief of Staff AI, and introduce the Ten Functional Systems roadmap. Over the following months, we install those systems one at a time — starting with your daily rhythm, then spreading into sales, marketing, and operations. Includes 30 days of async follow-up after the initial session.

03
60 Min · Monthly

1:1 Coaching Call

A private working session to unblock whatever is in front of you — a hard decision, a stalled team rollout, a messy process to re-architect with agents. Paired with the monthly system install so every coaching call advances a specific upgrade in your business.

04
Ongoing + Quarterly Review

Humans + Agents Platform (Your Team)

Your organization gets access to the Humans + Agents platform — the same infrastructure used to spread AI capability beyond the CEO. Includes team onboarding, a use-case library, and quarterly team adoption reviews. This is where your personal upgrades propagate into actual agent networks running sales, marketing, and operations.

What You Walk Away With

⚡

Your AI Operating System — in 30 Days

Daily rhythm, Chief of Staff AI, and personal file system fully installed and running within your first month.

🔧

3–4 Functional Systems in 90 Days

The first set of the Ten Functional Systems installed and measurable within your first quarter — not a roadmap, actual systems running.

🤝

A Trusted Peer Room

A confidential cohort of non-competing CEOs you rely on monthly — sharing what's actually working, not what sounds good in a pitch.

📈

Measurable Team AI Adoption

Quantified AI adoption across your team within 90 days — not vibes-based, measured through quarterly adoption reviews.

🧠

A Point of View You Can Lead With

A confident, clear perspective on AI you can share with your board, your leadership team, and your own people.

🏗️

All Ten Systems — in 12 Months

A concrete, measurable 12-month arc that ends with every functional system installed end-to-end across your organization.

The Rhythm

Monthly check-ins keep momentum between full quarterly roundtables — a cadence built around how CEOs actually work.

Month 1

Kickoff & First System Live

1:1 OS kickoff · First Executive Peer Board check-in · Team platform onboarding · First of the Ten Systems goes live.

Monthly Check-Ins

Install, Coach, Connect

Executive Peer Board check-in · 1:1 coaching call · Next functional system installed · Real-time learning sessions that unlock productivity immediately.

Quarterly Roundtable

Full Strategic Session

Deep-dive peer roundtable · Team AI adoption review (measured) · Progress tracked, gaps closed, next quarter planned.

12-Month Arc

Fully Installed

All ten functional systems installed across your organization, end-to-end. A competitive moat that compounds.

"Every month, the leader leaves with an upgrade running in their business — not a talk, not a slide, not a to-do list. Installed."

From the Peer Board

CEOs who are in the room — in their own words.

Working with Maureen and Laura, I built an operating system for how I actually lead — an AI-powered scoreboard for developing each of my leaders, a sharper rhythm for our one-on-ones, and a clear line on what every one of them can become. The AI didn't replace the coaching. It made me a better coach to my team.

Derek · CEO

The work Maureen and Laura started with us used to take a team of people and weeks of digging. Now it runs as a set of AI agents that hand me the intelligence and a system to act on it fast. We're getting ahead of the work instead of chasing it.

Greg · CEO

Years ago Maureen helped me turn a struggling team into a high-performing one. The discipline she taught me hasn't changed — but with an AI layer on top, one good habit a day, it compounds into something I couldn't have imagined. Same principles, turbocharged.

Lloyd · CEO

Laura has a very simple approach that is immediately actionable and makes it easy for teams to get started with AI. In just one simple session, Laura's ability to command attention and positively approach all of our sales challenges was artfully executed. Laura's passion for innovation and her expertise in moving deals through our funnel was performed more efficiently through the use of her AI prompts. While sales is a very human-to-human art form, Laura showed us how using AI one prompt at a time can be used to more effectively communicate our message so we can show even greater value to our customers through a more efficient buying experience. This hands-on approach to learning immediately created a new tool for my team to improve their game by leveraging AI to solve sales problems.

Tim · CEO, NJ-Headquartered Manufacturing Company

Your Facilitators

Led by two practitioners who work alongside CEOs every day — not theorists, operators.

Laura Ali

Laura Ali

Founder, Triple Win Sales

Laura is a 25-year sales executive and former leader at Fortune 100 companies Xerox Corporation and RR Donnelley, and held VP roles at high-growth startups Document Sciences (Xerox Venture Capital, led to IPO) and Smartmail. As President of Triple Win Sales since 2006, she has helped CEOs and sales leaders drive sustainable revenue growth through AI-driven strategy and systems. She brings a hands-on, immediately actionable approach to every session — her method: one AI prompt at a time, compounding into organizational transformation.

✦ Black Belt in Artificial Intelligence — SimpleAcademy.ai ✦ Certified CEO Peer Board Facilitator — The Alternative Board ✦ Strategic Doing Facilitator — Strategic Doing Institute
Maureen Ennis

Maureen Ennis

Thrive Digital Era

Maureen brings deep expertise in helping leaders navigate organizational transformation in the digital era. As co-facilitator of the Executive Peer Board and lead on the 1:1 operating system installs, she works alongside CEOs to close the gap between AI ambition and actual capability — turning personal upgrades into organizational leverage. Her approach: the same discipline that built high-performing teams for decades, now turbocharged with an AI layer on top.

Experience It Before You Commit

Not sure if this is the right room for you? Come sit in on a complimentary Executive Peer Board session — no obligation, no pitch. Just experience the conversation and see what it feels like to be in a room of CEOs actively installing AI into their organizations.

🎟️

Attend a Free Session

Join as a guest for one Monthly Executive Peer Board session. You'll leave with at least one real-time AI insight you can apply to your business immediately — with no commitment required.

Request Your Complimentary Guest Seat →

Subject to availability · One guest seat per session · 30-min intro call to confirm fit

The Membership

One relationship. Four components. A measurable 12-month arc.

Leading in the AI Era — Membership
Investment discussed on your discovery call
  • Monthly Executive Peer Board check-in + full quarterly roundtable
  • Real-time learning sessions that unlock productivity immediately
  • 1:1 AI Operating System Install (Ten Functional Systems)
  • 90-min onboarding kickoff + 30 days async follow-up
  • Monthly 1:1 coaching call — 60 minutes
  • Humans + Agents platform access for your team
  • Quarterly team AI adoption review (measured)
  • Facilitated by Laura Ali & Maureen Ennis
  • Curated cohort of 8–12 CEOs — confidential environment
Book Your 30-Min Discovery Call

Discovery call is complimentary and non-committal. Seats are limited — cohorts are intentionally kept small.

Questions Answered

What is Leading in the AI Era? +
Leading in the AI Era is a monthly CEO Executive Peer Board that combines real-time learning sessions, a personal 1:1 AI Operating System install, monthly coaching, and team-wide capability. Facilitated by Laura Ali and Maureen Ennis, it is designed for CEOs and senior leaders at $5M–$100M organizations who want to operationalize AI — not just learn about it.
What are the Ten Functional Systems? +
The Ten Functional Systems are the operating backbone every CEO needs to install — drawn from Steve Cunningham's CEO AI Operating System framework. We install them one at a time over your 12-month arc, starting with your daily rhythm and personal Chief of Staff AI, then moving into sales, marketing, and operations.
Do I need to be technical to benefit? +
Not at all. This is designed for CEOs and senior leaders, not engineers. Sessions focus on how to lead AI adoption and unlock productivity immediately — no coding or technical background required.
How does the monthly vs. quarterly cadence work? +
Members have monthly check-ins with the Executive Peer Board — focused, action-oriented sessions built around real-time learning and peer accountability. Every quarter, the group convenes for a full roundtable: a deeper strategic session covering team adoption results, system progress, and planning for the next quarter.
Can I attend a session before committing? +
Yes. We offer complimentary guest seats for CEOs who want to experience the Executive Peer Board before making any decision. Book a 30-minute discovery call and we'll confirm availability and fit — no pitch, no pressure.
How is this different from other AI learning programs or peer groups? +
Most programs are either peer groups (lots of opinions, no new capability) or learning programs (content you watch and forget). This combines both — plus a 1:1 operating system install and a team platform. The outcome standard is simple: every session ends with something installed and running in your business. Not a slide. Not a to-do list. Installed.

Ready to Install Your
AI Operating System?

Book a complimentary 30-minute discovery call with Laura or Maureen to see if Leading in the AI Era is the right fit for you and your organization.

Book Your 30-Min Discovery Call →

No pressure. No commitment. Just a conversation.