About
An outside perspective from someone who has done the work.
Groundwork Technology Advisors is led by Jon McAnnis, a technology executive with 30 years of experience leading engineering, platform, and product organizations across healthcare, insurance, financial services, and consumer products and platforms. He has served as CIO or CTO at eight organizations and has led post-acquisition technology integration, SOC 2 and HIPAA compliance programs, cloud migrations, and cybersecurity governance in regulated environments.
30
Years in technology leadership
8
CIO or CTO roles held
300
Largest engineering team led
3×
SOC 2 attestation lead
Services
Services
Engagements are structured around specific deliverables or defined retainer scopes. Every engagement starts with a conversation to make sure the scope is right before any work begins.
Technology Ecosystem Assessment
A structured review of your current technology environment covering systems, integrations, vendors, debt, and gaps. Delivered as a prioritized written document.
Learn moreEngineering Organization Assessment
A review of your engineering team's structure, delivery practices, Agile maturity, and DevOps practices, with specific observations and recommendations.
Learn moreTechnology Role and Organizational Design
Helping companies think through the right technology roles, reporting structures, and hiring profiles for their current stage of growth.
Learn moreSecurity and Compliance Readiness
A practical review of your posture against SOC 2, HIPAA, or NIST requirements. Delivered as a gap inventory with a prioritized list of recommended next steps.
Learn moreFractional CIO and CTO Services
Part-time senior technology leadership on a monthly retainer for companies that are not ready for a full-time executive hire.
Learn moreTechnology Roadmap Development
Working with your leadership team to develop a practical technology roadmap aligned to business priorities. Designed to be actionable by your existing team, not aspirational.
Learn moreAI Readiness Assessment
A structured assessment of where your organization stands with AI today: what tools are in use, what governance is missing, and whether your data environment is positioned to get real value from AI investment.
Learn moreSelf-assessment
Is your technology foundation ready for what's next?
Answer 12 questions about your technology environment and get an instant read on where you stand and where the gaps are. Takes about 3 minutes.
How engagements work
How engagements work
Fixed-fee project
A defined assessment with a specific written deliverable at the end. Scope, timeline, and fee are agreed upon before work begins. Appropriate for most assessment engagements.
Monthly retainer
Ongoing fractional CIO or CTO services at a defined time commitment per week. Scope is set at the start of the engagement and revisited as the relationship evolves.
Hourly or daily advisory
For companies that need a senior technology perspective on a specific decision or situation without committing to a larger engagement. Available by the hour or day.
Start with a conversation.
If you're not sure which engagement fits your situation, reach out. A brief call is usually enough to figure out whether there's a useful fit.