Background
The methodology described on this page is grounded in real experience. As an incoming CIO at a regional health plan that had recently completed an acquisition, one of the first responsibilities was a structured assessment of the combined technology environment across both entities. That engagement shaped the approach Groundwork now brings to similar situations. The deliverables, timeline, and outcomes described here reflect what that work produced and what it made possible.
Experience behind the approach
The methodology described on this page draws from engagements like these, conducted over 30 years in technology leadership.
M&A technology integration
Led technology due diligence and post-close integration for a multi-entity healthcare acquisition.
- The combined entity had two separate IT organizations, overlapping systems, unresolved vendor contracts, and no shared view of the technology environment across both entities.
- Scoped the combined environment, identified redundancies and gaps, and assessed vendor concentration risk across both organizations.
- Produced the integration roadmap the merged organization used to rationalize systems and consolidate vendors over 18 months.
SOC 2 Type II readiness
Guided three separate organizations through SOC 2 Type II readiness programs, each starting from an informal security posture.
- Each organization was starting with no prior audit experience and an unclear picture of where their gaps were relative to the Trust Services Criteria.
- Ran a gap assessment against the applicable criteria, produced a prioritized remediation plan, and managed the readiness process through to audit for each organization.
- Each engagement resulted in successful SOC 2 Type II attestation within the agreed timeline.
Technology assessment for a growing nonprofit
Conducted a full technology ecosystem assessment for a regional behavioral health organization with 300-plus staff following a major EHR transition.
- Leadership had no consolidated view of the technology environment after the EHR transition and needed a reliable baseline before setting priorities.
- Conducted structured interviews with executive and IT staff, reviewed systems and vendor relationships, and assessed compliance posture across HIPAA and related requirements.
- Delivered a landscape document, compliance gap review, executive priorities map, and 18-month roadmap within 90 days. Leadership described it as the first time they had a single, accurate picture of their technology environment.
The situation
The organization was a regional health plan that had recently acquired a smaller competitor. The combined entity had two separate IT organizations, overlapping systems, unresolved vendor contracts, and a technology roadmap that had been paused during the deal. Leadership needed a clear picture of what they had, what was at risk, and what to prioritize before committing to a post-merger integration plan. No single person had visibility across both environments, and the board was asking questions the existing team could not yet answer.
What a 90-day assessment engagement delivers
The following describes the scope and deliverables from that engagement, structured as a replicable approach Groundwork brings to similar situations. Organization details have been generalized. Actual scope, timeline, and fee for any Groundwork engagement are agreed upon before work begins.
Technology landscape document
A written inventory of every system in use: what it does, how it connects to other systems, where the known gaps and pain points are, and what the organization does and does not control.
Compliance and security review
A structured review of the organization's posture across HIPAA, applicable privacy regulations, and disaster recovery and business continuity. Delivered as a gap inventory with a prioritized action list.
IT team and organizational review
Structured conversations with each member of the IT team to understand workload, capacity, strengths, and gaps. The review surfaces role clarity issues and structural adjustments that can make the existing team more effective without adding headcount.
Executive priorities map
Individual conversations with each executive to understand what they need most from technology in their own words. The process surfaces alignment and misalignment that has been implicit but never documented, giving the leadership team a shared language for technology conversations.
18-month technology roadmap
A practical roadmap organized into near-term actions the existing team can begin immediately, medium-term initiatives addressing the most important gaps, and longer-term investments requiring additional planning. Designed to be realistic and executable from day one.
How the work typically unfolds
| Timeframe | Focus | Output |
|---|---|---|
| Weeks 1, 3 | Introductory conversations with executive team and IT staff. Review of current systems, documentation, and known issues. | Preliminary landscape notes shared with CEO |
| Weeks 4, 6 | Deeper dives into system configuration, compliance posture, vendor relationships, and team capacity. | Executive priorities map drafted for feedback |
| Weeks 7, 9 | Synthesis of findings. Draft deliverables prepared and reviewed informally with CEO before finalization. | Draft roadmap shared with CEO for review |
| Weeks 10, 12 | Final deliverables completed. Presentation to leadership team. | All five deliverables delivered |
Engagement models
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.
What organizations walk away with
Clarity
A complete, written picture of the technology environment shared across the full leadership team
Prioritization
A ranked list of technology investments with clear rationale, ending the debate about where to focus first
Compliance confidence
A documented gap inventory and action plan giving leadership an honest picture of their risk posture
Team alignment
Surfaced misalignment between what executives needed from technology and what the IT team understood those needs to be
Does this sound like your organization?
Every engagement starts with a conversation to make sure the scope is right. No pitch, just an honest discussion about whether there is a useful fit.