Tommy Stewart
Enterprise Transformation Executive
- linkedin.com/in/tds21
- tstewart@trinityadvisorysolutions.com
- 770.710.3977
- Tampa, FL ยท Open to Relocation
Executive Introduction
A career built where the market itself is changing.
Tommy Stewart is an enterprise transformation executive who has spent more than three decades helping organizations navigate periods of significant market transition.
Throughout leadership roles at Microsoft, SAP, Salesforce, Verizon, Teradata, and AI-native companies, he has consistently been recruited to build high-performing organizations, commercialize emerging technologies, and align executive strategy with disciplined execution.
His experience spans enterprise software, cloud computing, telecommunications, artificial intelligence, data and analytics, and Fortune 100 commercial leadership.
What Distinguishes Tommy
While many executives build successful businesses within established markets, Tommy's career has centered on helping organizations succeed when the market itself is changing.
Repeatedly recruited during major technology transitions in CRM, cloud, enterprise platforms, intelligent infrastructure, and AI, he has built a reputation for creating organizations capable of executing through uncertainty rather than simply reacting to it.
Enterprise Performance Is Built, Not Wished Into Existence.
Vision creates direction. Execution creates enterprise value. My responsibility as a leader is turning ambition into repeatable operating performance.
Education & Recognition
- Whitworth University: Bachelor of Arts, Business Administration
- Executive Education: Wharton (Executive Presence and Influence), Kellogg (AI and Digital Marketing), UC Berkeley Haas (AI Strategy and Governance)
- Thinkers360 2026: #11 Global AI Orchestration, Top 25 Data Center, Top 100 CRM and Sales, Top 200 Sales Thought Leadership
Common Questions
Who is Tommy Stewart?
- Tommy Stewart is an Enterprise Transformation Executive who has spent three decades leading commercial growth at Microsoft, Salesforce, Verizon, SAP, and Teradata, and is the founder of Trinity Advisory Solutions.
What companies has Tommy Stewart worked for?
- Tommy Stewart has held enterprise leadership roles at Microsoft, SAP, Salesforce, Verizon, and Teradata, including serving as the first Chief Revenue Officer at Aible.
What is Tommy Stewart's area of expertise?
- Tommy Stewart specializes in enterprise transformation, commercial growth, strategic enterprise accounts, executive decision quality, and AI commercialization.
What is The Fifth Quadrant?
- The Fifth Quadrant is an essay by Tommy Stewart arguing that the most disruptive enterprise technology competitors are building outside the categories the Gartner Magic Quadrant is designed to measure.
What is Trinity Advisory Solutions?
- Trinity Advisory Solutions is the advisory practice founded by Tommy Stewart, providing selective commercial growth and go-to-market advisory work to enterprise technology and PE-backed leadership teams.