Senior IT Assessment Services & Technology Due Diligence.
When Getting It Wrong Is Expensive.
Triple8 Advisory helps business owners and leaders understand complex IT environments, make high-stakes technology and operating decisions, and add senior governance where full-time leadership is unnecessary.
AI Readiness • Vendor & MSP Performance • Private Equity IT Assessment • M&A Technology Due Diligence
30+ Years of Enterprise IT Experience. Fortune 500 Perspective. Independent Judgment. No Junior-Team Handoffs.
Sr. IT Technical Assessment Services & Technology
Due Diligence
When Getting it Wrong Is Expensive.
How I Can Help
Assess. Decide. Govern.
Three ways to bring senior IT judgment into the situation without adding unnecessary overhead.
Assess
IT Assessment Services &
M&A Technology Due Diligence
Understand what you really have.
Independent assessments of IT services, governance, vendors, technology operations, acquisition targets, and operating environments.
You leave with: findings, risks, priorities, and recommended actions.
From $7,500
Decide
IT Decision Support, RFPs, Sourcing, & Vendor Selection
Make the decision with better information.
Senior support for RFPs, sourcing, vendors, service models, operating problems, platforms, and other high-stakes IT decisions.
You leave with: a clear recommendation and decision-ready rationale.
From $1,500
Understand what you really have.
Independent assessments of IT services, governance, vendors, technology operations, acquisition targets, and operating environments.
You leave with: findings, risks, priorities, and recommended actions.
From $7,500
Govern
Fractional IT Governance, ITSM, Vendor Management, & ServiceNow
Add senior oversight without another FTE
Fractional support for IT governance, service management, vendor management, technology priorities, and executive decision support.
You leave with: senior oversight, accountable actions, and an agreed operating cadence.
From $4,000/month
You Need to Know What Technology Reality You Are Inheriting
You are acquiring a company, evaluating an environment, or preparing for integration and need to understand the technology, cost, dependencies, risks, and first priorities.
A Critical Transition or Operating Model Is Not Working
Ownership is unclear, teams are disconnected, deadlines are moving, or the organization needs one workable model across services, vendors, and technology.
IT Performance Does Not Match the Report
SLAs may be green and dashboards may look fine, but the business is still frustrated, service confidence is falling, or the numbers are not telling the whole story.
A Vendor, Sourcing, or Technology Decision Is Too Important to Guess
You are selecting, renewing, replacing, challenging, or negotiating with a provider and need an experienced independent view before committing.
Bring me in when the issue is important, cross-functional, or expensive enough that independent senior judgment matters.
Where Rob Can Help
Common Reasons Clients Call
Real Operating Problems
Problems Solved
Selected examples of situations where unclear ownership, weak governance, vendor failure, transition risk, or operating complexity required senior intervention.
01
Green SLAs. Red business reality.
Monthly vendor SLAs were reporting green, but business leaders were experiencing poor service and losing confidence in IT. The CIO suspected contract value leakage and needed a fact-based view.
What changed: Rob reviewed the contract and SLA environment, exposed inaccurate vendor reporting, and identified approximately $3M in potential commercial exposure. IT leadership gained a clearer basis for vendor governance, recovery discussions, and corrective action.
02
Too many tools. Too much spend. No enterprise owner.
Ticketing and help desk tools were spread across IT, business units, regions, vendors, and support providers. The CFO's question was direct: why are there so many tools, why is pricing not better, and why is there no clear enterprise strategy?
What changed: Rob helped turn ServiceNow and Service Desk capability into a stronger internal value model. The work supported broader adoption, duplicate tool reduction, chargeback alignment, Service Catalog maturity, and better leverage from enterprise platform use.
03
The transition was failing. The deadline could not move.
A major insourcing program was approximately 45 days from a fixed deadline when key leadership resigned. Contractual timelines could not move, while vendor offboarding, knowledge transfer, service readiness, and retained-team coordination still had to be completed.
What changed: Rob stepped in as transition owner, clarified priorities, coordinated remaining activities, closed gaps between executive expectations and operational readiness, and drove the transition to completion on time. Critical offboarding finished before the deadline and the operating model moved forward without triggering penalty exposure.
04
The multi-provider model needed one operating agreement.
Retained teams, Tier-1 providers, third-party providers, and internal service groups needed one operating language for how services would be delivered, measured, escalated, governed, and improved. Without it, ownership, handoffs, collaboration, service expectations, and provider accountability could fracture..
What changed: Rob helped establish a common IT operating model and governance language across processes, SLAs, OLAs, XLAs, service obligations, and provider accountability. That language was incorporated into the MSA, SOW, and Governance Appendix for each Tier-1 vendor, creating a shared basis for multi-provider service management.
05
The offshore Service Desk needed to be built for more than RTB.
A new offshore Service Desk and Service Management function needed the right people, operating practices, and leadership foundation. The requirement extended beyond after-hours support to providing critical continuity capability for Americas operations.
What changed: Rob supported offshore interviewing, hiring, team buildout, coaching, training, and remote leadership until local management was ready to take over. Rob also helped design, source, contract, and deploy cloud-based call routing that enabled the offshore team to provide critical support during an Americas Service Desk disruption.
Why Rob
Senior judgment built from actually operating IT.
Rob Weldon’s career started close to the machinery of IT in print, tape, systems, and batch operations, then expanded through data center, application development, management, senior leadership, consulting, enterprise transformation, ServiceNow, ITSM, vendor governance, sourcing, and executive roles, including interim COO/CTO responsibilities.
That range matters. Rob can move from detailed conversations with Service Desk leaders, operations managers, developers, architects, security teams, and vendors into an executive discussion with a CIO without losing the thread.
He does not just know the questions to ask. He knows what question should come next because of the answer he just received.
Today, that same operating perspective includes the major shift AI is driving across IT. Two years of focused immersion have sharpened Rob’s view of where AI can responsibly improve service delivery, governance, decision-making, automation, and operating models, and where it should not be forced.
30+ Years
in IT
Across data center, operations, programming, service management, governance, sourcing, vendors, transformation, and executive leadership.
Enterprise IT Leadership
Led 100+ direct resources across complex IT functions, global services, major vendors, and business-critical operations.
Cross-Industry Experience
Banking, healthcare, manufacturing, outsourcing, technology, and global enterprise environments.
Operator-to-Executive Range
Moves from frontline and technical detail to CIO-level decisions without losing the operational thread.
Why Clients Bring Rob Into Complex IT Situations
At a Glance
Executive Operating Profile
Senior judgment beyond the dashboard, the org chart, and the explanation in the room.
Rob built his perspective from the operating floor to the executive table, across technical delivery, service management, infrastructure, vendors, sourcing, governance, transformation, and CIO/CTO/COO-level leadership.
He does not view those areas in isolation. Each answer changes the picture, exposes the next question, tests an assumption, or reveals a dependency elsewhere. He connects technical reality, business impact, cost, risk, ownership, and execution as the situation unfolds.
The result is depth, range, and real-world operating judgment that helps clients see more, miss less, make better decisions, and achieve better results.
Experience Behind the Judgment
Experience That Reveals What Others May Miss
Rob’s perspective comes from decades working across the full IT operating environment, from frontline operations and technical delivery through service management, infrastructure, sourcing, vendors, governance, transformation, and executive leadership.
The value is not knowing one part of IT deeply. It is knowing how the parts connect, where to look next, and what an answer means to the rest of the operating environment. — Rob Weldon
Triple8 Advisory
Independent Senior IT Operating Advisor. Provides independent senior judgment through Assess, Decide, and Govern engagements. Rob applies the Triple8 Integrated Operating Lens across the full IT environment to uncover material risks, hidden dependencies, ownership gaps, costs, operating weaknesses, and opportunities, then turns those findings into clear recommendations for decisions and practical next actions.
Triple8 Advisory
Independent Advisory, Technology & AI Operating Immersion. Following three decades in enterprise IT, Rob launched an independent advisory and research platform to deepen his work across IT operating models, governance, service management, vendors, sourcing, emerging technology, and AI. The two-year immersion included intensive hands-on exploration of generative and agentic AI, automation, governance implications, operating-model impacts, and practical enterprise use cases, while continuing voluntary advisory work around ServiceNow, ITSM, vendor governance, transformation, and executive decision-making. That period became the foundation for the Integrated Operating Lens and the current Triple8 Advisory model.
Jun 2024 — Aug 2026
Nov 2023 – Sep 2024
Amazon.com, LLC
Manager III, Global IT Deployment Resource Strategy. Built a Deployment Resource Management Office to improve demand intake, project forecasting, capacity planning, and resource governance across global deployment operations.
Jan 2021 – Nov 2023
Amazon.com, LLC
Manager III, Global IT Deployment Resource Strategy. Built a Deployment Resource Management Office to improve demand intake, project forecasting, capacity planning, and resource governance across global deployment operations.
Apr 2007 – May 2020
Nissan North America
Sr. Manager, IT Service Management, Vendor Governance, Strategy & Portfolio Leadership. Led Service Desk, ServiceNow/ITSM tooling, Service Management Integration, Demand Management, Infrastructure Strategy, Infrastructure PMO, and Vendor Governance through major sourcing-model transitions.
Dec 2006 – Apr 2007
UpSurge, LLC
Consultant, IT Service Management and Vendor Governance. Contracted by Nissan to support ITIL v2 rollout across multiple Tier-1 technology providers and strengthen outsourced service-provider governance.
Dec 2003 – Dec 2006
UpSurge, LLC
Consultant, Technology & Operations Management. Provided interim technology and operations leadership for a Nashville-based marketing company. Led the move from manual regional sales processes to a web-based sales and early CRM solution, reducing customer acquisition costs by more than 70%.
Apr 1996 – Dec 2002
Bank of America
Vice President, Data Center Operations. Led predictive and proactive data center management supporting Banking, Mortgage, Investment, Securities, and International Trade Finance business operations.
Sep 1993 – Apr 1996
Bank of America
Sr. Systems Programmer. Provided technical support for 300+ CICS and IMS regions across multiple data centers, and traveled to merger/acquisition companies to determine resource transition strategy.
Aug 1990 – Sep 1993
Richmond Memorial Hospital ( Bon Secours)
Systems Programmer / Data Center Infrastructure Specialist. Completed data center buildout, software installation, performance tuning, and problem resolution activities across mainframe, midrange, distributed, and Wintel systems and clinical applications supporting hospital and remote patient-care environments.
Earlier
Career
Foundation
Time Life (Time Warner) / James River Paper
IT Operations Specialist. Provided enterprise problem solving, production monitoring, automation thinking, and systems reliability support for mainframe and midrange systems, databases, applications, and storage.
Aug 2026 — Present
IT rarely behaves as a collection of separate functions. Service performance affects business confidence. Vendor decisions affect cost and control. Architecture affects operations. Governance affects accountability. People, process, technology, risk, finance, data, and execution constantly influence one another.
The Triple8 Integrated Operating Lens is designed to examine those connections together, follow the evidence across boundaries, and test assumptions as the picture changes.
The result is a clearer picture of what is happening, why it matters, and what should happen next.
COBIT
Governance, accountability, controls, risk, and decision rights.
PMP / PMBOK
Structured project planning, dependencies, risks, milestones, and execution discipline.
IT4IT
Technology value flow across strategy, planning, delivery, operations, and improvement.
Agile/Scrum
Fast feedback, accountability, prioritization, and visible progress.
SIAM
Service integration, ownership, and accountability across multiple providers.
ITIL
Service ownership, management practices, performance, and continual improvement.
AIGP
Responsible AI adoption, governance, controls, risk, and operating model implications.
Lean Six Sigma
Process improvement, waste reduction, variation, and root-cause discipline.
To Connect the Dots, You Have to Understand the Full IT Picture
“The agentic future will not run on isolated frameworks or disconnected tools. It will require people who know how to integrate governance, service, risk, delivery, vendors, data, platforms, controls, and execution into one working system.” - Rob Weldon
Eight core frameworks. Three key views. One operating lens.
The Triple8 Integrated Operating Lens
Optional Follow-on Support
Where Rob Can Stay Engaged
Every assessment and decision engagement is designed to stand on its own. When continued senior involvement would add value, Rob can remain engaged through separately scoped support in selected areas.
Service Management
& Governance
SMO strategy, service performance, ServiceNow governance, operating discipline, SLAs/XLAs, service integration, service improvement, ITIL practices maturity.
Operating Models
& Transition
Functional ownership, decision rights, responsible AI, transition governance, M&A integration, transformation readiness, cross-functional operating models, and complex organizational change.
Vendors, Sourcing
& Outsourcing
RFI/RFP support, provider selection, sourcing strategy, vendor accountability, MSP governance, outsourcing transitions, contract operating and governance models, and multi-provider integration.
Popular Questions
Common Questions
Bring Me Into The Situtation
Tell me what you are working through, what decision is in front of you, and when you need help. We can quickly determine the best next step and whether an Assess, Decide, or Govern engagement makes sense.