Groundwork Technology Advisors was founded by Jon McAnnis, a technology executive with 30 years of experience leading IT and engineering organizations. Across his career, Jon has served as CIO or CTO at eight organizations and has run technology functions ranging from 20 to 300 people.
His deepest expertise is in healthcare and insurance, where he has held CIO and CTO roles at Providence Health Plans, Optum International, Western Reliance, ZoomCare, Humankind, and CMD. He has also led technology in financial services and consumer products and platforms, giving him a practical view of what works and what does not in environments where trust and reliability are table stakes.
Groundwork Technology Advisors exists to bring that experience to small and mid-size companies that need senior technology leadership without the cost of a full-time hire. The practice is deliberately focused on assessment, organizational design, security and compliance readiness, and fractional leadership engagements where a seasoned practitioner can deliver meaningful impact quickly.
Credentials include CHIME certification as a Healthcare CIO, Information Security Leader, and Digital Health Executive, a master's degree in Engineering and Technology Management, and the Chief AI Officer certification (AI CERTs, in progress).
Experience across each service area
Technology Ecosystem Assessment
The firm's principal has conducted technology landscape assessments at multiple organizations as part of CIO onboarding and strategic planning cycles, producing documented inventories of systems, integrations, vendor relationships, and technical debt that served as the foundation for multi-year technology roadmaps.
Engineering Organization Assessment
Has built and led engineering organizations ranging from 20 to 300 people across eight CIO and CTO roles. Has assessed and restructured engineering teams, clarified roles and accountability frameworks, and implemented delivery practices that measurably improved output quality and predictability. At one organization, elevated system uptime from 75 percent to 98.5 percent through engineering culture and process improvements. At another, drove Agile delivery efficiency from 65 percent to 95 percent across a 300-person engineering team.
Technology Role and Organizational Design
Has hired and developed technology leadership teams across multiple organizations at different stages of growth, from early-stage startups to established enterprise organizations. Has defined technology org structures and hiring profiles appropriate to each company's growth stage and strategic priorities.
Security and Compliance Readiness
Has led SOC 2 attestation at three separate organizations while serving simultaneously as CISO and CIO. Has built NIST-aligned cybersecurity programs from the ground up. Has deep experience with HIPAA compliance in clinical and insurance environments, and has prepared organizations for regulatory audits and maintained compliance in CMS-regulated Medicare Advantage and Medicaid environments.
Fractional CIO and CTO Services
Has served in CIO and CTO roles at organizations that did not previously have a technology executive, building technology functions and leadership capability in environments where none existed. Understands what it takes to provide senior technology direction in organizations with lean teams and constrained resources.
Technology Roadmap Development
Has developed and executed multi-year technology roadmaps across multiple organizations, translating business strategy into technology investment priorities. Has led stakeholder alignment processes with C-suite partners including CEOs, CFOs, CMOs, and COOs to ensure roadmaps reflect organizational priorities rather than technology team assumptions.
Why Groundwork Technology Advisors exists
Many small and mid-size companies are making technology decisions without a clear picture of where they stand today or a practical plan for where they are going. An experienced outside perspective can help with both.
That is what Groundwork Technology Advisors is designed to provide. The firm works with a small number of clients at a time and structures engagements around specific deliverables: a written assessment, a practical roadmap, or consistent senior leadership on a retainer basis. Not open-ended relationships that extend beyond their useful life.
Have a question or want to discuss a potential engagement?
Reach out by email or phone. Most conversations start with a brief call to understand the situation before discussing whether there is a useful fit.