Leadership
Proven executive leadership with deep experience guiding complex enterprises through high-consequence transformation.
Leadership You Can Trust With Enterprise-Scale Decisions
Watchman Global Alliance is led by executives who have personally led the kinds of large-scale, complex, and high-risk transformations that enterprises now face.
This is not academic expertise.
It is experience earned through direct accountability for outcomes — across global enterprises, critical infrastructure, and sovereign environments.
Bob Sweezie
Founder & Principal | Watchman Global Alliance
Bob Sweezie is the founder and principal of Watchman Global Alliance and serves as the firm’s lead orchestrator for enterprise-scale cybersecurity and digital transformation initiatives.
With more than four decades of experience in executive leadership, alliance development, and global partner orchestration, Bob has built and led trusted ecosystems across the world’s most respected technology, cybersecurity, and consulting organizations. His work has supported enterprises, critical infrastructure operators, and governments operating at national and global scale.
Bob is a co-creator of Watchman Analysis™, the firm’s portfolio analysis and capability assessment model used by sovereign governments, global system integrators, critical infrastructure operators, and private equity firms. The model provides defensible, regulator-ready insight aligned to dozens of global standards and is designed to support enterprise decision-making under scrutiny.
As an orchestrator, Bob’s leadership focus is clear:
Assemble the right ecosystem for the enterprise
Ensure alignment across vendors, integrators, and consultants
Enable outcomes without bias or conflict of interest
Bob leads Watchman Global Alliance as a neutral, trusted convener, ensuring enterprise objectives — not vendor agendas — drive execution.
Clifton N. B. Triplett
Founder & Global Subject Matter Expert – Cybersecurity, Risk, and Manufacturing Systems
Clif Triplett is a globally recognized cybersecurity, risk, and enterprise systems executive with deep experience across commercial industry, government, and defense environments.
Clif has held senior executive leadership roles at some of the world’s most complex enterprises, including General Motors, Motorola, Baker Hughes, and Entergy, where he was responsible for global IT, manufacturing systems, quality, and cybersecurity operations at scale. His leadership spans environments involving thousands of facilities, highly regulated operations, and mission-critical systems.
In government, Clif served as a Presidential Executive Fellow for IT and Cybersecurity under the Obama Administration, where he led cybersecurity remediation efforts following the OPM breach and contributed to the development of federal Zero Trust architecture and national-level cyber response models in coordination with DHS, NSA, DISA, and the National Security Council.
Clif is a co-creator of Watchman Analysis™ and serves as the firm’s lead subject matter expert for cybersecurity, risk strategy, and manufacturing and engineering system portfolios. His experience uniquely bridges:
Cybersecurity and risk governance
Large-scale manufacturing and engineering systems
IT / OT integration
Enterprise transformation under regulatory and operational constraints
He is a graduate of the United States Military Academy at West Point and holds a master’s degree in Computer Information Systems from Boston University.
Why This Leadership Matters
Enterprises engage Watchman when decisions must be:
Defensible to Boards and regulators
Executable across global operations
Grounded in reality, not theory
Aligned across technology, risk, and operations
Watchman leadership brings:
First-hand experience leading complex transformation
Pattern recognition across industries and geographies
Credibility with executive, operational, and technical stakeholders
The judgment required when trade-offs matter
This leadership foundation enables Watchman to operate as a trusted advisor and orchestrator in environments where failure is not an option.