A structured review of a company's current technology environment including systems, integrations, vendor relationships, technical debt, and known gaps. Delivered as a written document with findings organized by priority.
This engagement is useful for companies that need a clear, objective picture of where their technology stands before making investment decisions, hiring technology leadership, or preparing for a transaction. It is not a sales document and does not advocate for a particular vendor or platform. The goal is an honest inventory of where things are, with observations on what matters most.
What this engagement delivers
- A written inventory of every system in use, how it connects, and what the organization does and does not control
- A vendor relationship review covering contracts, concentration risk, and performance gaps
- A technical debt assessment with observations on what is slowing delivery or creating operational risk
- A prioritized findings document organized by what matters most, not by category
“Jon led our team through an assessment of our current technology platform and organizational capabilities, including a build vs. buy analysis, to give our business partners real options and clear recommendations. His biggest contribution was championing a shift that made technology decision-making an organizational process rather than a technology-only process. He built relationships across the company so that stakeholders understood what was possible and could participate in selecting the best path forward. The roadmap we produced was designed to solve genuine business problems while bringing a legacy tech stack up to date, always treating technology as a servant of the business.”
Senior Director, Application Development, Clearway Health
A review of the engineering team's structure, delivery practices, Agile maturity, DevOps practices, and capacity relative to what the organization is asking of it. Includes specific observations and recommendations on role clarity, team structure, and development priorities.
Useful for leadership teams that want better visibility into their technology organization and an outside perspective on what is and is not working. The engagement involves structured conversations with engineering leaders and, where appropriate, individual contributors, along with a review of how work is planned, tracked, and delivered.
What this engagement delivers
- A structured review of team composition, role clarity, and capacity relative to current demands
- An assessment of delivery practices including sprint planning, Agile maturity, and CI/CD pipeline health
- Specific observations on what is working, what is not, and what changes would have the most impact
- A written recommendations document the leadership team can act on without an engineering background
“Jon inherited an in-house electronic medical records system that had been built quickly and was showing the consequences: stability problems, quality issues, and a legacy codebase that had become genuinely difficult to work with. Rather than treating it as a delivery problem to be outrun, he brought in quality assurance specialists, hired the right experts, and built a more rigorous software delivery pipeline that gave the team far greater confidence in what was going out the door. At the same time, he incrementally replaced components of the legacy system with modern architecture, sequenced thoughtfully so ongoing operations were never disrupted. He also created room to build things right rather than maintaining singular pressure to ship as fast as possible, which is a difficult shift to achieve politically in most organizations. The result was a system and a team that the business could actually rely on.”
Enterprise Architect, Velocity Made Good
Helping companies think through the right technology roles, reporting structures, and hiring profiles for their current stage of growth. Includes a review of the current structure, identification of gaps, and recommendations on role definitions and what to look for in future technology hires.
Particularly useful for companies that are not sure whether their current technology leadership structure matches what the business needs next. Many companies reach a point where they have outgrown their current setup but are not certain what the right next step looks like. This engagement helps clarify that question and produces concrete, specific guidance rather than generic frameworks.
What this engagement delivers
- A review of the current technology org structure and where it does not match the company's current stage
- Role definitions and reporting structure recommendations specific to the company's situation
- A hiring profile for any technology leadership role the company needs to fill next
- Guidance on what to look for in candidates that is grounded in the company's actual environment
“Jon has a clear-eyed understanding of how engineering organizations need to be structured at different stages of a company's growth, and he's particularly skilled at balancing long-term investment in full-time talent with the elastic capacity that contracting organizations can provide. Under his leadership, FTEs and contractors don't operate as two separate tiers , they function as a unified team with shared standards and shared accountability. He also handles underperformance with a combination of humanity and decisiveness that is rare: he holds both the individual and the organization in mind simultaneously. The result is a leadership team that doesn't depend entirely on Jon to function well, which is exactly what you want from a fractional CIO.”
Enterprise Architect, Velocity Made Good
A practical review of your security and compliance posture against SOC 2, HIPAA, NIST, or other frameworks relevant to your industry. Delivered as a gap inventory with prioritized next steps.
Useful for companies preparing for an attestation cycle, responding to customer security questionnaires, or tightening posture after a compliance or security event. Common across healthcare, insurance, financial services, and regulated SaaS.
What this engagement delivers
- A gap inventory against the applicable framework, SOC 2, HIPAA, or NIST, with findings organized by severity
- An honest assessment of what it would take to get audit ready and how long it would realistically take
- A prioritized remediation list the leadership team can use to assign ownership and track progress
- A written deliverable leadership can share with auditors, insurers, or board members as evidence of active remediation
“Jon viewed cybersecurity, compliance, and risk management as core business functions rather than standalone IT activities, which meant security had real executive visibility in our organization. What stood out most was his ability to lead through complex compliance and risk initiatives while keeping leadership focused on outcomes instead of just meeting requirements. During periods of growth and operational change, he aligned executive leadership, technology teams, and security initiatives in a way that improved accountability, governance, and overall organizational maturity. He understood how to balance security requirements with operational realities, which made large initiatives far more achievable and sustainable.”
CISO, OnPoint Credit Union
Part-time senior technology leadership on a monthly retainer, typically one to two days per week. Useful for companies that need a seasoned technology executive guiding strategy, engineering delivery, vendor decisions, and security posture without the cost of a full-time hire.
My fractional clients typically come from healthcare, insurance, financial services, and consumer products and platforms, usually in the 50 to 500 employee range.
What this engagement delivers
- Senior technology leadership available one to two days per week without a full-time executive salary
- Ongoing ownership of technology strategy, vendor relationships, and engineering team direction
- A senior technology voice in leadership meetings, board conversations, and key vendor negotiations
- Continuity of technology direction during a leadership transition or gap
“Jon has a clear-eyed understanding of how engineering organizations need to be structured at different stages of a company's growth, and he's particularly skilled at balancing long-term investment in full-time talent with the elastic capacity that contracting organizations can provide. Under his leadership, FTEs and contractors don't operate as two separate tiers , they function as a unified team with shared standards and shared accountability. He also handles underperformance with a combination of humanity and decisiveness that is rare: he holds both the individual and the organization in mind simultaneously. The result is a leadership team that doesn't depend entirely on Jon to function well, which is exactly what you want from a fractional CIO.”
Enterprise Architect, Velocity Made Good
Working with a company's leadership team to develop a practical technology roadmap aligned to business priorities. Starts with structured conversations with key stakeholders to understand what they need from technology, synthesizes those inputs into a prioritized view of technology investments, and produces a phased roadmap organized into near-term actions and longer-term initiatives.
The roadmap is designed to be actionable by the existing team rather than aspirational. The goal is not a slide deck that gets filed away. It is a working document that gives the organization a shared, realistic picture of where technology is going and why.
What this engagement delivers
- Structured stakeholder conversations with each executive to surface what they actually need from technology
- A prioritized technology investment plan organized into near-term actions and longer-term initiatives
- A phased roadmap document the existing team can execute against without outside help
- Alignment across leadership on technology priorities, ending the recurring debate about where to focus
“Jon inherited an in-house electronic medical records system that had been built quickly and was showing the consequences: stability problems, quality issues, and a legacy codebase that had become genuinely difficult to work with. Rather than treating it as a delivery problem to be outrun, he brought in quality assurance specialists, hired the right experts, and built a more rigorous software delivery pipeline that gave the team far greater confidence in what was going out the door. At the same time, he incrementally replaced components of the legacy system with modern architecture, sequenced thoughtfully so ongoing operations were never disrupted. He also created room to build things right rather than maintaining singular pressure to ship as fast as possible, which is a difficult shift to achieve politically in most organizations. The result was a system and a team that the business could actually rely on.”
Enterprise Architect, Velocity Made Good
AI is showing up in your organization whether you planned for it or not. Your staff is using it daily. Your vendors are embedding it in the tools you already pay for. The question is no longer whether AI is part of your technology environment. It is whether you have the visibility, governance, and readiness to use it well and avoid the risks that come with using it poorly.
This engagement delivers a written assessment with specific, prioritized recommendations your leadership team can act on. It is structured as a fixed-fee project with scope and fee agreed before work begins, and is typically completed in 30 to 45 days.
What this engagement delivers
- An inventory of AI tools and capabilities already in use across your organization, including shadow adoption your IT team may not be tracking
- An honest assessment of your data environment and whether it supports the AI use cases you are considering
- A governance gap review covering acceptable use policy, data handling, vendor AI terms, and regulatory exposure
- A prioritized set of recommendations organized by what to do first, what to defer, and what to avoid
Fixed-fee engagement. Scope and fee agreed before work begins. Typically completed in 30 to 45 days.
“Jon understood that scalable AI and meaningful business intelligence require a strong data foundation first. One of the most valuable initiatives he led was building a new, scalable data layer that unified fragmented systems, improved data integrity, and created reliable infrastructure for analytics, reporting, and future AI capabilities. Without it, inconsistent data quality would have limited our ability to measure outcomes, support enterprise growth, or credibly demonstrate business impact. His work significantly improved data confidence, operational scalability, and strategic decision-making while positioning us for more advanced predictive capabilities over time.”
Former SVP of Product, Self-Employed
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