Services

“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.”

“Jon's approach to assessment is one of his quieter strengths. He asks the right questions and leads an organization to its own conclusions, aligning the team to industry best practices while making it feel like the team's own mission to solve. Across two enterprise organizations under his leadership we executed system consolidations, cloud migrations, and modernized QA practices that meaningfully increased speed and agility. On the vendor side, his deliberate diversification strategy drove better performance from every partner and proved more cost effective than the single-vendor approach many organizations default to.”

“Jon distilled the quality and age of our home-built technology stack independently from what those systems actually did, which allowed us to assess the stack's needs separately from the question of whether to keep our internally developed EHR or go off the shelf. That clarity guided us through an EMR system decision that had not been seriously evaluated in 15 years of do-it-yourself development. Without that separation of concerns, we would have conflated two very different questions and likely made a worse call.”

“We had a good understanding of our gaps in our data systems, but what we did not have was a good understanding of gaps in our alignment with future strategic directional shifts. Jon provided executive and financial air cover for data work that required non-trivial investment and time. Beyond that, he worked directly with our CEO to read the tea leaves and prepare us for multiple eventualities.”

“We spent years struggling with complex business rules related to medical providers and network agreements, trying everything from custom builds to vendor purchases without success. Jon recognized that what we truly needed was master data management, a framing none of our previous efforts had landed on. He structured the problem in a way that finally allowed us to contend with the complexity and reduce the error and chaos that had plagued us.”

“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.”

“What stood out about Jon's approach to defining roles and structuring the organization was his ability to align the team with the company's stage and evolving business priorities. He built a strong foundational team responsible for the core software platform and then adjusted roles and responsibilities as the company's direction and project scope changed. Jon was pragmatic about organizational design, understanding that early-stage and growth-stage companies require flexibility. As business needs evolved, he refined the organization by adding capabilities, redefining responsibilities, and ensuring the right people were in place to support both immediate priorities and long-term objectives.”

“Jon moved our engineering team away from a traditional waterfall model to shorter development cycles, which made a real difference in how quickly we could respond to changing business needs. The improvement in predictability and transparency stood out most to us as a business. He established a communication and feedback process that gave stakeholders genuine visibility into priorities, progress, and timelines. Engineering became consistently aligned with what the business actually needed, and we had confidence that the right work was being delivered on time and with the quality required.”

“Jon put a team of leaders in place, including me, and then guided us as we built out the engineering organization. He drew on an extensive network of leaders and strong direct contributors, and provided direct guidance to our interviewing and scaling process. He helped determine the size and composition of the team against our short-, mid-, and long-term goals, then aligned our full-time headcount and operating expenditures to the anticipated long-term state. He also identified and managed partners to provide augmentation out of capital expenditure budgets to deliver on several major builds.”

“Across three organizations I worked in under Jon, we built nearshore and offshore models using a pod and SIP vendor approach, always anchored by in-house technical leadership that owned the architecture, the roadmap, and the standards. What made the model work was a single decision: vendor teams and internal teams were held to the same KPIs, so there was no ambiguity about what success looked like regardless of which company's badge someone wore. Internal leadership owned technical direction while vendors brought capacity and execution inside that frame, which meant we could flex up or down on cost without ever losing institutional knowledge. That clarity is what kept the model durable across multiple companies.”

“Jon led full Scaled Agile and DevOps transformations at two enterprise-level organizations I worked in under him, and he didn't just adopt the frameworks, he made them stick. Delivery became predictable, and business stakeholders started trusting engineering commitments again. The cultural shift was as significant as the operational one: turnover dropped, engineers wanted to stay, and engineering went from being a cost center the business tolerated to a function it relied on. That credibility compounded over time and changed how engineering was perceived in roadmap conversations, budget cycles, and executive planning.”

“Jon and I worked together on building out the data team at HumanKind, and his knowledge was invaluable in determining the right mix of staff, both in functional roles and levels of experience. What set him apart from other CIOs I had worked with was that he structured the team to match our company's actual goals and culture rather than simply replicating what he had built elsewhere. He intuitively understood how to design an IT function that fit a small to mid-size company, not just on paper but in practice.”

“Before Jon engaged with our engineering teams, we had no real rigor around sprint estimation or completion. With his leadership, our story point completion rate jumped from 50 to 60 percent per sprint into the mid-80 percent range, well within accepted industry standards. He held teams accountable to monitor their own completion rates and finish what they committed to each sprint.”

“Jon approached engineering team structure with real intentionality, making sure organizational design matched both our growth stage and strategic priorities. What stood out most was his ability to balance immediate delivery needs with long-term organizational maturity, hiring leaders and technical talent not just for execution, but for scalability, adaptability, and culture fit. His emphasis on role clarity across engineering, product, and data significantly improved collaboration, accountability, and execution efficiency.”

“Jon brought much-needed structure and operational discipline to engineering delivery by implementing clearer prioritization frameworks, realistic roadmap planning, and stronger cross-functional coordination between product, engineering, and data teams. His transparency around tradeoffs, risks, and capacity helped leadership make better-informed decisions. As a result, delivery became more predictable, teams operated with greater velocity and focus, and speed increased without sacrificing technical integrity or team morale.”

“Jon joined when we had a structure that was headcount-heavy in data but skills-weak. He evaluated this quickly against our actual business needs, updated role definitions, set clear expectations, and hired from both his network and outside sources. He also knew when our stage called for converting people in place rather than bringing in new hires, which mattered because we were not in a big spend mode. The result was a significantly skilled-up group delivering at pace and with consistently high quality, at a lower overall cost.”

“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.”

“What stood out about Jon's approach to defining roles and structuring the organization was his ability to align the team with the company's stage and evolving business priorities. He built a strong foundational team responsible for the core software platform and then adjusted roles and responsibilities as the company's direction and project scope changed. Jon was pragmatic about organizational design, understanding that early-stage and growth-stage companies require flexibility. As business needs evolved, he refined the organization by adding capabilities, redefining responsibilities, and ensuring the right people were in place to support both immediate priorities and long-term objectives.”

“Jon put a team of leaders in place, including me, and then guided us as we built out the engineering organization. He drew on an extensive network of leaders and strong direct contributors, and provided direct guidance to our interviewing and scaling process. He helped determine the size and composition of the team against our short-, mid-, and long-term goals, then aligned our full-time headcount and operating expenditures to the anticipated long-term state. He also identified and managed partners to provide augmentation out of capital expenditure budgets to deliver on several major builds.”

“Across three organizations I worked in under Jon, we built nearshore and offshore models using a pod and SIP vendor approach, always anchored by in-house technical leadership that owned the architecture, the roadmap, and the standards. What made the model work was a single decision: vendor teams and internal teams were held to the same KPIs, so there was no ambiguity about what success looked like regardless of which company's badge someone wore. Internal leadership owned technical direction while vendors brought capacity and execution inside that frame, which meant we could flex up or down on cost without ever losing institutional knowledge. That clarity is what kept the model durable across multiple companies.”

“Jon and I worked together on building out the data team at HumanKind, and his knowledge was invaluable in determining the right mix of staff, both in functional roles and levels of experience. What set him apart from other CIOs I had worked with was that he structured the team to match our company's actual goals and culture rather than simply replicating what he had built elsewhere. He intuitively understood how to design an IT function that fit a small to mid-size company, not just on paper but in practice.”

“Jon approached engineering team structure with real intentionality, making sure organizational design matched both our growth stage and strategic priorities. What stood out most was his ability to balance immediate delivery needs with long-term organizational maturity, hiring leaders and technical talent not just for execution, but for scalability, adaptability, and culture fit. His emphasis on role clarity across engineering, product, and data significantly improved collaboration, accountability, and execution efficiency.”

“Jon joined when we had a structure that was headcount-heavy in data but skills-weak. He evaluated this quickly against our actual business needs, updated role definitions, set clear expectations, and hired from both his network and outside sources. He also knew when our stage called for converting people in place rather than bringing in new hires, which mattered because we were not in a big spend mode. The result was a significantly skilled-up group delivering at pace and with consistently high quality, at a lower overall cost.”

“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.”

“Jon integrated security and compliance into our core technology strategy at Zoomcare rather than treating them as afterthoughts. He maintained strong oversight of our SOC 2 and HIPAA compliance initiatives and placed significant emphasis on business continuity and disaster recovery planning. His steady attention to these areas meant the appropriate controls, policies, and recovery plans were always in place. That leadership gave us real confidence that we were prepared for audits, regulatory expectations, and unexpected disruptions.”

“SOC2 compliance is an area a lot of companies downplay or delay because they misunderstand what it requires or see it as an operational burden. Jon sponsored the SOC2 program and brought the team together to identify process improvements that led to documented, repeatable processes and audit successes. The work he drove turned a perceived burden into a foundation we could actually build on.”

“Jon built our security program from scratch in one organization and matured an existing one in another, moving the second team from reactive remediation to a proactive posture within two years. We self-audited annually against SOC 2, PCI, HIPAA, and ISO, rolling course corrections into regular delivery cycles rather than treating them as separate projects. When a near-miss incident occurred, Jon gave the technical team space to diagnose while working directly with legal and the FBI, compressing what could have been months of work into four or five days. The final outcome was that only extremely low-risk IP was exposed and all customer data was confirmed safe.”

“Jon assessed where we were, where we needed to be, and built a plan to get us there while continuously reassessing risk as the threat landscape shifted. He moved us from fragmented, non-scoped security issues to SOC 2 compliance within 18 months, all within a complex environment of multiple vendors, platforms, and interoperability requirements. That kind of structured progress across a messy vendor landscape is not easy to pull off.”

“Jon managed the noise of the IT function, worked with our executives on business strategy, then developed a series of options and ultimately a plan that was coherent and executable. Our outside board had deep industry and IT backgrounds and was concerned about our SOC status and our EHR platform. Jon's ability to work across the board and our executive team allowed the board to approve a significant financial investment to move forward.”

“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.”

“Jon moved our organization away from annual planning commitments toward a quarterly planning cadence, which gave the business a far more honest and actionable view of what technology could deliver. He participated actively in bi-weekly executive leadership sessions, helping business leaders engage with the roadmap as a living document rather than a fixed plan. His approach to build versus buy decisions stood out because he was never dogmatic , every decision was evaluated on its own merits, through the lens of what was actually right for the business at that stage. That intellectual honesty consistently led to decisions that held up well over time.”

“Jon moved our engineering team away from a traditional waterfall model to shorter development cycles, which made a real difference in how quickly we could respond to changing business needs. The improvement in predictability and transparency stood out most to us as a business. He established a communication and feedback process that gave stakeholders genuine visibility into priorities, progress, and timelines. Engineering became consistently aligned with what the business actually needed, and we had confidence that the right work was being delivered on time and with the quality required.”

“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.”

“Jon's approach to assessment is one of his quieter strengths. He asks the right questions and leads an organization to its own conclusions, aligning the team to industry best practices while making it feel like the team's own mission to solve. Across two enterprise organizations under his leadership we executed system consolidations, cloud migrations, and modernized QA practices that meaningfully increased speed and agility. On the vendor side, his deliberate diversification strategy drove better performance from every partner and proved more cost effective than the single-vendor approach many organizations default to.”

“Jon led full Scaled Agile and DevOps transformations at two enterprise-level organizations I worked in under him, and he didn't just adopt the frameworks, he made them stick. Delivery became predictable, and business stakeholders started trusting engineering commitments again. The cultural shift was as significant as the operational one: turnover dropped, engineers wanted to stay, and engineering went from being a cost center the business tolerated to a function it relied on. That credibility compounded over time and changed how engineering was perceived in roadmap conversations, budget cycles, and executive planning.”

“Jon assessed where we were, where we needed to be, and built a plan to get us there while continuously reassessing risk as the threat landscape shifted. He moved us from fragmented, non-scoped security issues to SOC 2 compliance within 18 months, all within a complex environment of multiple vendors, platforms, and interoperability requirements. That kind of structured progress across a messy vendor landscape is not easy to pull off.”

“Jon distilled the quality and age of our home-built technology stack independently from what those systems actually did, which allowed us to assess the stack's needs separately from the question of whether to keep our internally developed EHR or go off the shelf. That clarity guided us through an EMR system decision that had not been seriously evaluated in 15 years of do-it-yourself development. Without that separation of concerns, we would have conflated two very different questions and likely made a worse call.”

“Jon is not just technology-focused. He has excellent soft skills that are invaluable in building a team. As VP of Data and Analytics, I saw him hold our data team accountable where needed while also having our back with the rest of the business. When our company was significantly upgrading its technical and data offerings, Jon's participation at a senior leadership forum was especially helpful in convincing company leadership to exhibit the patience and perseverance needed to roll out those changes in a way that actually mattered to the business.”

“Jon assembled a team to review our technology and data roadmap, covering workstreams across architectural improvements, coding standards, and data contracts. The data contracts work was particularly useful, creating enforceable agreements between our technology and data teams and the business that defined how data should be structured, validated, and governed as it moves through its pipelines. This gave us a concrete framework for accountability between technical and business stakeholders that we had not had before.”

“Jon played a critical role in shaping our technology strategy by ensuring the roadmap was grounded in both business priorities and technical scalability. He consistently aligned technology investments to operational realities, product goals, and future growth needs. What stood out most was his ability to modernize our platform strategy while maintaining delivery continuity, balancing innovation with pragmatism. He championed architectural decisions that improved platform scalability, governance, and long-term flexibility, so the organization could evolve efficiently as business needs expanded.”

“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.”

“Jon brought much-needed structure and operational discipline to engineering delivery by implementing clearer prioritization frameworks, realistic roadmap planning, and stronger cross-functional coordination between product, engineering, and data teams. His transparency around tradeoffs, risks, and capacity helped leadership make better-informed decisions. As a result, delivery became more predictable, teams operated with greater velocity and focus, and speed increased without sacrificing technical integrity or team morale.”

“We had a good understanding of our gaps in our data systems, but what we did not have was a good understanding of gaps in our alignment with future strategic directional shifts. Jon provided executive and financial air cover for data work that required non-trivial investment and time. Beyond that, he worked directly with our CEO to read the tea leaves and prepare us for multiple eventualities.”

“Jon's key contribution for us was identifying and championing a specific path to data quality and data responsiveness. The roadmap he laid out included multiple business checkpoints, continue/redirect/halt type evaluations, and pre-defined goals for each phase. We knew our problem overall, but we did not know how to get from current to desired state. Jon showed us that viable path, and then guided us on execution of it.”

“Jon has an amazing way of designing a technology roadmap and strategy that balances infrastructure and stability with experimentation and innovation. He keeps tech debt in check while still supporting business growth, and he brings business and tech stakeholders together in a way that produces a plan everyone can buy into.”

“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.”