Tommy Stewart

Founder and Executive Commercial Officer at Trinity Advisory Solutions

Tampa, United States

Tommy Stewart is ranked #11 globally in AI Orchestration by Thinkers360, with additional 2026 recognition in the Top 100 for CRM & Sales and Top 25 for Data Center.

For more than twenty years, his core has been CRM and enterprise sales optimization, the discipline underneath every account he has run, across technology, telecommunications, and media industries at Microsoft, SAP, Salesforce, Verizon, and Teradata. He carried that discipline into AI decision intelligence as Aible's first Chief Revenue Officer, then formalized it through AI Strategy and Governance at UC Berkeley's Haas School of Business. The technology keeps changing. The pattern doesn't: diagnose the constraint, align leadership around a practical operating model, and build the execution discipline that converts vision into measurable results.

His record includes growing Verizon's Walt Disney Company account from $6.2M to $12M while architecting a five-year, $600M technology roadmap across six global theme parks and building Verizon's first enterprise Content Delivery Network offer; closing a $167M enterprise renewal and structuring a $50M Azure commitment for the Disney relationship at Microsoft, earning the company's Top Client Director Award; delivering $59M on the Disney portfolio at Salesforce, including an $18M Disney Streaming agreement; and building Teradata's Media & Entertainment business from $58M to $137M, closing a $22M agreement with DIRECTV. As Aible's founding Chief Revenue Officer, he grew pipeline from $4.8M to $18.4M and ARR from $2.1M to $5.7M in a category with no established buying motion.

Today, through Trinity Advisory Solutions, he applies that same discipline as a principal, not an employee. As the sole commercial lead on a confidential GenAI platform, he built $12M in pipeline in 90 days with no existing commercial infrastructure to build from.

Motivation fades. Calibration persists.

Available For: Advising, Speaking
Travels From: Tampa FL

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

Tommy Stewart	Points
Academic	0
Author	32
Influencer	22
Speaker	0
Entrepreneur	20
Total	74

Points based upon Thinkers360 patent-pending algorithm.

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CRO 3.0: The Chief Orchestration Officer and the Future of Revenue Leadership

The CRO title is having an identity crisis — and most executives don't know it yet. The role that was built for control, consistency, and quarterly precision is now architecturally obsolete. Not struggling. Obsolete. The real question isn't whether organizations will make the transition to AI-native revenue orchestration. It's whether their leaders will be the ones who architect it, or the ones who get replaced by someone who will.

What the Session Delivers
• A definitive framework for the three evolutionary phases of CRO leadership — and why the current playbook has reached its natural endpoint
• The five core competencies of the Chief Orchestration Officer: Digital Transformation Leadership, Data-Driven Decision Making at Speed, Strategic Systems Thinking, Change Leadership, and AI-Powered Customer Centricity
• A concrete transition roadmap from revenue management to intelligence orchestration — with phase-by-phase milestones and risk mitigation
• Live diagnostic: audience members benchmark their organizations against the orchestration maturity model in real time
• The compounding advantage mathematics: why a 6-month head start in orchestration compounds into a nearly insurmountable competitive gap within 3 years

The Quadrant Tells You Who Won the Last Market. The Fifth Quadrant Is Where the Next One Is Being Built.

Enterprise technology leaders spend billions validating their position on the Magic Quadrant. The most dangerous competitors they face have stopped trying to move through it entirely.

The Fifth Quadrant is the space outside the grid where category-rewriting, AI-native disruptors are building right now — not unmeasured because they are too small or too early, but unmeasured because the methodology was designed for the category they are dismantling. By the time the quadrant can place them, the window for incumbents to respond has often already closed.

This session delivers three things Gartner audiences rarely hear from a single speaker: the insider's account of how category obsolescence actually unfolds — told by someone who operated inside the commercial architecture of every major enterprise software transition over 25 years; the analytical framework to identify Fifth Quadrant threats before the analysts can name them; and the Third Pricing Epoch intelligence — the agentic billing transition restructuring enterprise software contracts right now while most renewal teams are still buying against seat counts.

Attendees leave with a self-diagnostic, a five-question contract renewal playbook, and a fundamentally different way of reading the quadrant they walked in trusting

Trinity Advisory Solutions

Founder and Executive Commercial Officer

https://trinityadvisorysolutions.com

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

Agentic AI

AI 30.01

AI Infrastructure

AI Orchestration 34.05

Analytics 30.53

Business Strategy 30.03

Careers

Change Management

Coaching

Creativity

CRM 30.06

Data Center 31.27

Digital Disruption

Emerging Technology 30.03

Entrepreneurship

Innovation 30.31

Leadership 30.15

Management

Marketing

Predictive Analytics

Sales 32.85

Startups

Telecom

Transformation

Venture Capital 30.65

Industry Experience

High Tech & Electronics

Media

Professional Services

Telecommunications

Publications & Experience

8 Article/Blogs

The Fifth Quadrant: Why the Most Dangerous Competitors Have Already Left the Grid
LinkedIn Newsletter
April 02, 2026

A forward-looking brief exploring emerging categories, unconventional competitors, and the shifts rewriting enterprise technology today. The Disruptors.

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Tommy Stewart

Founder and Executive Commercial Officer at Trinity Advisory Solutions

Tampa, United States

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

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