Practical IT leadership for growing organizations
Rook helps growing, multi-site, and regulated organizations improve Microsoft 365, IT operations, SaaS governance, and technology decision-making without adding a full-time IT executive.
Principal-led • Vendor-independent • Experienced in multi-site and regulated environments • Defined, usable deliverables
Choose how to work with Rook
Start with a free checkup
A 30-minute screen share of your Microsoft 365 setup. You leave with your top 5 fixes. No pitch.
Purchase a defined outcome
Best for clients who already know the deliverable they need and want a clear scope, timeline, and starting point.
Request a tailored scope
Best for implementation, ongoing advisory work, project oversight, or needs that cross multiple service areas.
Where Rook helps
Microsoft 365 and Collaboration
Improve how Microsoft 365 and collaboration platforms are governed, licensed, organized, and used. Rook identifies configuration and ownership gaps, clarifies priorities, and develops an improvement roadmap that fits the organization's actual capacity.
View related engagementsIT Operations and Governance
Bring structure to service management, SaaS ownership, employee access, documentation, and recurring operational processes. The goal is a technology function that is easier to manage, support, and maintain.
View related engagementsFractional IT Leadership
Add experienced technology leadership for a defined initiative or ongoing advisory need. Rook supports planning, vendor decisions, project oversight, executive communication, and operational accountability.
View related engagementsStart with a defined project
These are fixed-scope engagements with a clear deliverable, defined timeline, and a starting price. If you know what you need, you can get started directly on Upwork.
Microsoft 365 Assessment & Prioritized Improvement Roadmap
Organizations using Microsoft 365 without a clear governance or optimization strategy.
- Tenant configuration review
- Prioritized improvement roadmap
- Actionable recommendations document
Starting at $1,500
View Project Details on UpworkIT Operations Assessment & 90-Day Improvement Roadmap
IT teams looking to improve service delivery, reduce operational debt, or establish clearer ownership.
- Current-state operations review
- Gap and risk summary
- 90-day prioritized improvement plan
Starting at $1,500
View Project Details on UpworkIT Onboarding & Offboarding Workflow Design with SOPs
Organizations with inconsistent or undocumented employee lifecycle processes.
- Documented onboarding workflow
- Documented offboarding workflow
- Standard operating procedures
Starting at $1,500
View Project Details on UpworkWays to work with Rook
Free, 30 minutes
Free Microsoft 365 checkup
A screen share of your Microsoft 365 setup. You leave with your top 5 fixes. No pitch.
$450 fixed
M365 Lockdown
We fix your top 5 security and access gaps. For teams up to 25 users.
$1,500 to $2,500
Fixed-scope projects
Microsoft 365 Assessment & Roadmap, IT Operations Assessment & 90-Day Roadmap, Onboarding and Offboarding SOPs.
From $1,500/month
Fractional IT leadership
Teams under 50 staff. From $3,500/month for 50 to 100 staff.
Built for organizations that have outgrown informal IT
Rook is best suited for growing, multi-location, remote, regulated, or privacy-sensitive organizations that rely heavily on technology but do not need another full-time technology executive. Typical clients have a small internal IT team, significant vendor dependence, unclear system ownership, inconsistent processes, or more technology initiatives than they can manage effectively.
Experienced IT leadership, not a vendor
Rook brings the perspective of someone who has run IT operations, managed teams, and made real technology decisions. Not a sales organization with a product to push.
Practical and outcome-focused
Every engagement is oriented toward clear, usable deliverables. Assessments produce prioritized recommendations. Projects produce documented outcomes. Nothing is designed to extend the engagement.
Honest about fit and scope
If a project is outside scope or a different approach would serve you better, Rook will say so. The goal is to help you move forward, not to fill a statement of work.
A straightforward engagement process
Initial conversation
We discuss the organization, the immediate problem, and the outcome you need.
Defined scope
Rook confirms the objectives, boundaries, timeline, deliverables, and information required.
Assessment and delivery
The current state is evaluated and findings are translated into usable recommendations, documentation, or project direction.
Next-step support
If additional help is needed, implementation or advisory support can be scoped separately.
Founded and led by Jeremiah Reed
Principal Consultant, Rook Technology Consulting
Jeremiah Reed is an experienced IT Director and hands-on technology leader. His background includes leading technology operations in a complex, multi-site healthcare environment, with experience spanning Microsoft 365, IT service management, SaaS governance, vendor management, employee lifecycle processes, documentation, project delivery, and technology roadmaps. Before entering IT, Jeremiah served in a U.S. Army communications role. Rook is intentionally principal-led: clients work directly with the consultant responsible for understanding the problem, developing the recommendations, and delivering the work.
The goal is a technology environment that works reliably, scales with the organization, and does not require heroics to maintain.
Ready to move forward?
Choose the path that fits where you are.
Free, 30 minutes