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Tommy Stewart

CEO & Founder at Trinity Advisory Solutions

Tampa, United States

Tommy Stewart is ranked #11 globally in AI Orchestration by Thinkers360.

Twenty-two years. One pattern. The gap between where a business is and where it needs to be is almost never a talent problem. It's an architecture problem.

Tommy has spent two decades building commercial systems inside and alongside the most consequential technology transitions of the last generation, from the earliest Azure enterprise agreements at Fortune scale to AI revenue engines built in categories that didn't have a buying motion yet. His work has spanned Verizon, Microsoft, SAP, Salesforce, and Aible, where he served as founding CRO with personal capital at risk, growing qualified pipeline from $48K to $18.4M in a category with no established buying motion.

As the creator of the MAIKER Framework™ and the Competitive Separation model, Tommy has operationalized a systematic approach to intelligent revenue operations across 300,000+ enterprise technology seats — adopted by CROs, CEOs, and founders navigating the shift from legacy GTM models to AI-native operating systems. His frameworks start from a premise most organizations resist: most have built an advantage, but almost none have built structural separation.

His thinking sits at the intersection of revenue strategy, organizational design, and applied AI. That combination shows up in the room, not on a slide deck.

Through Trinity Advisory Solutions, an active operating practice, Tommy partners with forward-thinking leadership teams to engineer the shift from reactive to orchestrated, from tool-dependent to intelligence-driven, and from incremental to exponential, compounding performance.

He is not just advising on the future of revenue. He is building it.

Available For: Advising, Consulting, Speaking
Travels From: Tampa FL

Speaking Fee $3,500 (In-Person), $1,500 (Virtual)

Tommy Stewart Points
Academic 0
Author 31
Influencer 22
Speaker 0
Entrepreneur 20
Total 73

Points based upon Thinkers360 patent-pending algorithm.

Thought Leader Profile

Portfolio Mix

Company Information

Company Type: Individual
Theatre: United States
Minimum Project Size: $1,000+
Average Hourly Rate: $300+
Number of Employees: 1-10
Company Founded Date: 2019
Media Experience: 8 years
Last Media Interview: 08/14/2025

Areas of Expertise

5G
Agentic AI
AI
AI Infrastructure
AI Orchestration 35.05
Analytics 30.53
Business Strategy 30.03
Change Management
Coaching
Creativity
CRM 30.06
Data Center 31.27
Digital Disruption
Digital Twins
Entrepreneurship
Innovation 30.32
IT Strategy 30.19
Leadership 30.15
Marketing
Sales 32.87
Smart Cities
Startups
Telecom
Venture Capital

Industry Experience

High Tech & Electronics
Media
Professional Services
Telecommunications

Publications & Experience

7 Article/Blogs
Why I Don't Coach Soft Skills to Elite Sales Teams (And You Shouldn't Either)
Linkedin
January 18, 2026
Let's talk.

If you're still coaching ambition, motivation, courage, and grit to your high-performance sales teams in 2026, you're already behind.

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Tags: Analytics, Data Center, Sales

"Invent and Simplify" Became "Integrate and Delegate"
Linkedin
December 08, 2025
What AWS re:Invent 2025 reveals about the cloud's real next chapter, By Tommy Stewart

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Tags: Analytics, Data Center, Sales

An Open Letter To All CEOs Betting on Agentic AI
Linkedin
October 10, 2025
These announcements are being positioned as victories for technology. But they also send a darker message celebrating the replacement of people by machines. The very employees who built your companies, carried escalations, and poured themselves into your platforms are now being told their contributions are no longer needed.

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Tags: Analytics, Data Center, Sales

Why Enterprises Need an AI Playbook Before an AI Platform
Linkedin
August 24, 2025
AI is no longer optional. Enterprises are investing billions in platforms, tools, and pilots to capture the promise of artificial intelligence. Yet, according to Gartner, up to 85% of AI initiatives fail to deliver business value. The reason is rarely technical. Instead, the breakdown occurs within the organization itself in leadership alignment, cultural readiness, and change management.

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Tags: Analytics, Data Center, Sales

Enter the Chief Orchestration Officer: The Maestro of Enterprise Chaos
Linkedin
August 21, 2025
Move over, CIO. Step aside, COO. Sorry, CRO (both of you). There’s a new sheriff, or better yet, conductor in town: The Chief Orchestration Officer (COO)* is the executive responsible for weaving together the symphony of enterprise chaos with a baton of AI, legacy duct tape, and just a touch of caffeine-fueled wizardry.

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Tags: Analytics, Data Center, Sales

Rethinking the Stack: Why Intelligent Orchestration Will Obliterate the SaaS Chaos We Created
Linkedin
August 19, 2025
The Enterprise Stack Is Broken—And You Know It

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Tags: Analytics, Data Center, Sales

The Race to Relevance
Linkedin
August 15, 2025
Picture this:You’re a seasoned seller, with a sharp suit, good shoes, and a pipeline full of “warm” prospects.

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Tags: Analytics, Data Center, Sales

14 Author Newsletters
“The Real Decision Behind Every Salesforce Renewal”
Linkedin
April 02, 2026
Across the Fortune 500, a quiet but consequential reckoning is underway. The question is no longer whether to reconsider Salesforce. It's whether you have the architecture to address it before your next renewal date locks you in for another cycle.

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Tags: Business Strategy, CRM, IT Strategy

Execution Drift Is Not a Failure. It Is a Pattern.
Linkedin
March 06, 2026
Enterprise organizations do not lose control of execution suddenly. They surrender it incrementally. One deferred decision. One granted exception. One tolerated deviation at a time. By the time leadership recognizes that execution has degraded, the behaviors that caused it are normalized.

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Tags: AI Orchestration, Data Center, Sales

The System Isn't Broken. We Built It This Way.
Linkedin
February 19, 2026
Over the past couple of years, I noticed a pattern that kept showing up across very different clients. Despite the variations, a common thread began to emerge.

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Tags: Analytics, Data Center, Sales

The Platform Inflection Point: Why Your Next CRM Decision Is Really an Architecture Decision
Linkedin
February 17, 2026
For twenty-five years, CRM decisions were procurement events.

Today, they are architectural commitments.

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Tags: Analytics, Data Center, Sales

What It Takes to Advance a Cross-BU Enterprise Platform Deal
Linkedin
February 13, 2026
The enterprise platform opportunity looked perfect on paper. Three business units aligned on the timeline. Executive sponsors committed. RFP responses submitted. Then a senior operations leader sent a single email to Finance: "Do we really need this now?"

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Tags: Analytics, Data Center, Sales

Orchestrating AI Without Losing the Human Core
Linkedin
February 06, 2026
The most challenging aspect of moving from managing people to orchestrating agents is not technical. It is psychological.

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Tags: AI Orchestration, Data Center, Sales

My Sales Team Are AI Agents: The Leadership Paradigm Nobody's Talking About
Linkedin
February 05, 2026
The conversation in every boardroom sounds the same: "How do we use AI to make our sales team more productive?" Wrong question. The right question: "When do I stop managing humans who use AI tools and start orchestrating AI agents who occasionally need human intervention?"

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Tags: AI Orchestration, Data Center, Sales

The First 90 Days as SVP of Sales or CRO Are Not About Strategy—They’re About Command
Linkedin
January 29, 2026
Most incoming revenue leaders arrive with a plan. A strategy. A roadmap. A mandate to grow.

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Tags: AI Orchestration, Data Center, Sales

To the 13,000 Verizon Colleagues Now Navigating Tomorrow
Linkedin
November 21, 2025
This week, Verizon announced the elimination of more than 13,000 positions, its largest single layoff in company history, joining a pattern we've witnessed across Fortune 100 companies throughout 2024 and 2025. New CEO Dan Schulman cited the need to "evolve as a company" by slashing costs and restructuring operations.

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Tags: Data Center, Sales

Salesforce: Why Many Enterprises Are Outgrowing the Legacy Model
Linkedin
November 14, 2025
In boardrooms everywhere, one quiet truth is emerging: many organizations have outgrown the CRM architecture they built the last 10–20 years around Salesforce.

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Tags: Analytics, Data Center, Sales

You Are the Organization: Building Your Skills Portfolio for the Future of Work
Linkedin
November 13, 2025
Corporate America is facing a reckoning. According to recent McKinsey research, up to 30% of work hours could be automated by 2030, with generative AI accelerating that timeline dramatically. Goldman Sachs estimates that AI could impact 300 million full-time jobs globally. But here's what the headlines miss: this isn't just about job losses; it's about a fundamental transformation in how work itself is structured.

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Tags: Data Center, Sales

Leading with Grit Ch. 6: The Emotional Resilience Edge
Linkedin
November 12, 2025
Let’s get one thing straight: Emotional resilience is not optional. If you’re an executive, a sales leader, or anyone steering a team through high-stakes environments, your ability to bounce back and bring others with you is what separates average from elite.

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Tags: Analytics, Data Center, Sales

The Rise of the Intelligent Solutions Orchestrator (ISO): The New Superhero
Linkedin
September 29, 2025
Enterprise sales is broken. Deals crawl. Stakeholders stall. And just when you think you’re close? Enter the consultants, parachuting in with hourly rates that would make your CFO choke on their coffee.

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Tags: Data Center, Sales

AI Has Pulled Back the Green Curtain on CRM, and It’s Not Pretty
Linkedin
September 03, 2025
For 30 years, CRM has been the Wizard of Oz of sales tech: loud, expensive, and utterly convinced of its own importance. Behind the curtain? Armies of sellers wasting hours feeding systems that give nothing useful back.

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Tags: CRM, Data Center, Sales

1 eBook
CRO 3.0
dersignrr.io
October 24, 2025
The Chief Revenue Officer role is undergoing its most profound transformation since its emergence two decades ago. What began as a sales leadership position evolved into revenue integration and now faces a fundamental reimagining driven by artificial intelligence, changing buyer behavior, and the accelerating speed of business.

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Tags: AI Orchestration, Innovation, Leadership

2 Executives
Verizon Business
Verizon Business
July 01, 2021
You’re more than a business, agency or organization leader. We’re more than the usual network that provides reliable coverage. Together, we can empower you and your people.

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Tags: Sales

Marlabs LLC
Marlabs LLC
February 01, 2018
Marlabs designs and develops digital solutions with data at the center. We leverage our deep data expertise and cutting-edge technology to empower businesses with actionable insights and achieve improved digital outcomes.

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Tags: Data Center

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