Advisory and project leadership
Independent advice for projects that can’t slip.
I work with small businesses planning their next step, and with executives, CIOs, and private equity teams facing an acquisition, a carve-out, a fixed cutover date, or a program that has started to drift. You get someone who has run this work from the inside, and a clear read on where the risk actually is.
Andrew WeinbergPrincipal, Adaptive Technology GroupWhen it makes sense to call
Most engagements start with one of these situations.
- Your IT grew one fix at a time, and nobody has a picture of how it all fits together.
- You’re moving email, files, or systems, and the business can’t lose a day doing it.
- A deal has closed, and the integration plan is still a slide rather than a plan.
- You’re separating a business, and the transition services clock is already running.
- A go-live date is fixed, and nobody can say what happens if it goes wrong at 2 a.m.
- Every status report is green, and the program keeps missing dates anyway.
- Leadership is getting updates, but not the decisions it needs to make.
- You need a senior lead in the seat for a defined phase, not another consultant’s deck.
Engagements
Each one is scoped in writing before work starts, with a defined deliverable.
Planning and delivery
Project management
For a technology project with a deadline and more moving parts than your team has time for: an office move, a system rollout, a vendor change. I build the plan, run the schedule and the vendors, and keep you informed in plain terms until it’s done.
You get: a written plan and schedule, managed vendors and tasks, and a clean close-out with documentation.
Migration planning
Before you move email, files, or systems, whether to Microsoft 365, to the cloud, or off an aging server. I inventory what you have, map what has to move and in what order, and plan the cutover so the business keeps running.
You get: an inventory, a sequenced migration plan with rollback steps, and a cutover checklist.
IT architecture for small and growing businesses
For a business whose IT grew one fix at a time. I look at how your network, devices, accounts, and applications fit together, and design what they should look like for the next few years.
You get: a map of what you have today, a target design, and a prioritized roadmap you can budget against.
Integrations, cutovers, and recovery
Integration readiness review
For an acquisition or divestiture, before or just after close. I map systems, identity, contracts, and dependencies on both sides, find what gates Day 1 and TSA exit, and sequence the work so both organizations can act on it.
You get: a written assessment, a sequenced integration roadmap with named decision owners, and an executive readout.
Cutover risk assessment
An independent review before a high-stakes go-live. I test the plan against reality: rollback triggers, go/no-go criteria, decision authority, rehearsal coverage, and the dependencies nobody has put on the critical path.
You get: a readiness verdict, a prioritized list of what to fix before the window, and a decision framework for the night itself.
Program recovery
For an initiative that has stalled or started to drift. I separate real risk from noise, find where ownership and dependencies have broken down, and reset governance so leadership sees exposure early.
You get: a recovery plan, a re-baselined critical path, and reporting that surfaces decisions instead of status.
Leadership in the seat
Fractional program leadership
When you need senior leadership running the program, not just advice about it. I step in as interim program lead for an integration, carve-out, or platform transition, and hand off cleanly to your team.
You get: hands-on leadership for a defined phase, with governance and documentation your team can keep running.
Fractional CTO
For a private equity–backed or growth-stage company without a technology leader. I lead technology for a defined period, covering architecture, vendors, staffing, and cost, and report to leadership in terms of risk, dates, and dollars. We confirm the fit in the first conversation.
You get: a technology roadmap, vendor and staffing plans, and leadership until a permanent hire is in place.
Security and compliance program leadership
For an organization facing an audit, a regulatory deadline, a cyber-insurance requirement, or a security program that exists mostly on paper. I turn findings and requirements into a sequenced program with named owners and realistic dates, so remediation actually closes.
You get: a gap-to-plan roadmap, a remediation tracker with owners, and executive reporting through the deadline.
Where this experience comes from
All stories at andrewweinberg.usMoved St. Francis Hospital and 13 clinics between two health systems in a single cutover.
Read the storyOnboarded two acquisitions in parallel at Qualifacts, run as a standalone program with its own governance.
Read the storyCut downtime on Asurion logistics systems carrying $1.5 million a day in exposure.
Read the storyAlso: helped build Windows Update at Microsoft · Vanderbilt Epic rollout and 22,000-endpoint Windows 10 migration · Jefferson / Einstein disaster recovery and business continuity transformation · 25+ years across healthcare IT, enterprise infrastructure, SaaS, and M&A integration.
How engagements work
Every engagement starts with a conversation about the situation: what’s at stake, what the deadline is, and what has already been tried. If I’m not the right fit, I’ll say so.
Scope, deliverables, and timeline are agreed in writing before work begins. I take on a small number of engagements at a time so each one gets real attention.
Adaptive Technology Group is the firm that contracts the work, and I’m its principal. My background and longer writing are at andrewweinberg.us.
Tell me what’s at stake.
Describe the project, the deadline, and what worries you. I’ll give you an honest read on whether I can help.