Strategic Technology Leadership for Executives
Navigate technology complexity with confidence. Get CIO level insights on tech investments, risk management, and strategic positioning without the full time executive commitment.
When You Need CIO Level Thinking Without the Full Time Executive
Evaluating Major Tech Investments
Should you build or buy? Cloud or on premise? How do you justify ROI to the board while managing technical risk?
Managing Cybersecurity & Compliance Risk
Navigating evolving regulations, implementing security frameworks, and convincing leadership that prevention beats crisis response.
Building IT Leadership Capability
Your team is strong technically but needs strategic guidance. How do you elevate thinking from operations to business enablement?
Modernizing Legacy Infrastructure
Balancing operational continuity with innovation. What's the right migration path that won't bring the business to a halt?
Our Strategic Advisory Approach
Practical wisdom from 25+ years navigating boardroom strategy and server room reality. We translate technology complexity into executive clarity.
Context Discovery
We start by understanding your business drivers, not your tech stack. What’s the board pressure? Where are operational bottlenecks? What keeps your CEO awake at night?
- Business context assessment
- Stakeholder interviews (board, executives, IT leadership)
- Current capability mapping
- Risk & opportunity identification
Strategic Options Analysis
We present technology choices as business decisions ROI, risk, timing, and organizational readiness. No vendor bias, no tech jargon without translation.
- Technology landscape assessment
- Build vs. buy economic modeling
- Risk-adjusted ROI scenarios
- Vendor evaluation frameworks (when applicable)
Executive-Ready Recommendations
Deliver clear, defensible recommendations designed for board level consumption. We prepare you to confidently present technology strategy as business strategy.
- Strategic roadmap with investment timeline
- Risk mitigation frameworks
- Board presentation materials
- Decision support documentation
Implementation Support (Optional)
Strategy without execution is hallucination. We can guide implementation, coach your team, or stay engaged as a sounding board for emerging decisions.
- Ongoing advisory retainer
- Implementation oversight & coaching
- Vendor negotiation support
- Change leadership facilitation
What You Receive
Actionable intelligence designed for executive decision making, not shelfware.
Technology Strategy Roadmap
12-36 month phased plan with investment priorities, risk mitigation, and success metrics
Investment Business Cases
Board ready ROI analysis with assumptions, alternatives, and sensitivity modeling
Risk Assessment Frameworks
Cybersecurity, compliance, operational continuity, and vendor lock in mitigation strategies
Vendor Evaluation Criteria
Objective scorecards for technology selection, RFP templates, negotiation playbooks
Governance Structures
Decision rights, oversight committees, KPI dashboards, and accountability frameworks
Executive Briefing Materials
Board presentation decks, one pagers, and talking points for stakeholder communication
Common Advisory Scenarios
Organizations engage us when facing these critical decision points:
"We're being pitched a $2M ERP system is this the right move?"
What we assess:
- Vendor claims vs. your actual requirements
- Total cost of ownership (licensing, integration, training, customization)
- Organizational change readiness
- Alternative solutions (build, modular SaaS, phased approach)
- Contract negotiation leverage points
Typical outcome: 30-40% cost reduction through right-sizing scope, alternative architectures, or better commercial terms. Sometimes the answer is “yes, but not like this.”
"Our IT costs keep rising but business value isn't clear"
What we diagnose:
- Technology portfolio rationalization (eliminate redundancy)
- Service provider contract optimization
- Licensing compliance and usage optimization
- Outsourcing vs. in-house economic models
- Value-based budgeting frameworks
Typical outcome: 15-25% operational cost reduction while improving service levels. Establish business aligned investment governance.
"We need to modernize but can't afford downtime"
What we architect:
- Strangler pattern migration strategies
- Parallel run frameworks with fallback plans
- Data migration risk assessment
- Business continuity planning during transformation
- Phased rollout with value realization checkpoints
Typical outcome: Zero downtime modernization roadmaps. Turn “big bang” risk into managed, reversible steps.
"Our CIO just left what's our interim strategy?"
How we stabilize:
- Emergency technology leadership (fractional CIO role)
- Critical decision making continuity
- Team stabilization and knowledge capture
- Vendor and stakeholder relationship management
- Permanent CIO recruitment support (requirements, screening)
Typical outcome: 3-6 month continuity bridge while you find the right permanent leader. No strategic drift, no vendor opportunism.
"We're expanding regionally how do we scale technology?"
What we plan:
- Standardization vs. localization trade offs
- Infrastructure architecture for multi country operations
- Data sovereignty and compliance requirements
- Shared services vs. federated IT models
- Technology M&A integration playbooks
Typical outcome: Scalable technology blueprint that balances efficiency with local market needs. Avoid the “copy paste then fix” trap.
"The board wants a digital transformation plan yesterday"
What we deliver:
- Rapid strategic assessment (current state, opportunity mapping)
- Business capability mapping to technology enablers
- Prioritized transformation roadmap with quick wins
- Investment framework and governance model
- Board presentation materials with defensible assumptions
Typical outcome: 4-6 week intensive engagement producing a credible 18-36 month transformation plan. Enough detail to act, enough flexibility to adapt.
“Jared didn’t just give us a technology plan he translated our business ambitions into a roadmap the board could actually understand and fund. His ability to bridge technical depth with executive communication saved us from a $3M mistake and set us on a sustainable modernization path.”
Chief Financial Officer
Regional Financial Institution
Ready to Make Technology Decisions with Confidence?
Schedule a confidential advisory session. No sales pitch just strategic insight from someone who’s navigated these challenges hundreds of times.
First consultation: Strategic assessment of your most pressing technology decision no commitment required.
Complementary Services
Digital Strategy
Turn CIO insights into comprehensive digital transformation roadmaps
Project Delivery
Execute the strategic plans with precision implementation management
Data Governance
Ensure technology decisions rest on trusted, well-governed data foundations