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Fractional CIO

Fractional CIO partner for the systems that cannot drift.

When your systems carry real operational risk, the problem is rarely one tool. It is the drift between decisions, data, vendors, and the humans who still have to run the business.

I come in as a fractional CIO partner and stay close enough to help the work actually land.

Dmitri Sunshine
23+ years
building systems that had to hold
~80 clients
served through a bootstrapped ERP SaaS company
Hands-on
implementation plus oversight

The fit

I am useful when the system is already important and the handoffs are getting expensive.

The best fit is an owner or operator who has real work stuck between tools, teams, vendors, and half-trusted reports.

I can step in as the senior partner who sees the technical risk and the operating cost at the same time.

Brittle systems that still carry daily operations.

Messy handoffs between internal teams and outside vendors.

AI pressure without a clear human control model.

Migration risk where one bad cutover can hurt the business.

What I can take off your plate

Implementation help with founder-level judgment.

I can work as a fractional CIO first, with CTO and COO depth when the work crosses architecture, process, accountability, or execution.

Fractional CIO roadmap

Turn tool sprawl into a decision path your team can run without false comfort.

Data migrations

Plan data migrations with validation steps, rollback choices, and a cutover path that does not depend on luck.

Systems integrations

Design systems integrations and API flows that reduce manual re-entry instead of hiding new operational drag.

AI agents

Build internal AI agents with human review, permission boundaries, and clear ownership of the next decision.

CRM, ERP, and reporting

Clean up the operating layer around CRM, ERP, dashboards, and recurring reports so people can trust what changed.

Security and resilience

Review cybersecurity, disaster recovery, vendor risk, and continuity plans with proof instead of policy theater.

How I work

Careful transition, not rip and replace.

I am not coming in to replace everyone or shame the stack you already have. I want to keep what works, reduce hidden risk, and help the next version of the system hold under pressure.

Use what works

I start by finding what is already carrying value, because ripping out a system can create more risk debt than it removes.

wrap before replace

When the existing system still has a useful core, I build the safer operating layer around it first.

Verify before trust

Backups, migrations, reports, and AI outputs need proof under pressure before they become part of the operating system.

Keep humans in control

AI should make the next decision clearer; it should not hide accountability behind a confident answer.

Why this is different

You get the pattern recognition of someone who has carried the whole thing.

I have been the founder responsible for payroll, the architect responsible for the data, and the operator who gets called when the handoff breaks.

That history changes the work because I am watching for quiet failure before it becomes visible.

23+ years in the work

I have built, scaled, fixed, sold, supported, and operated systems where bad assumptions became real cost.

Exited founder/operator

I bootstrapped an ERP SaaS company to around 80 clients and carried regulated data for more than a decade.

COO context

I have stepped into the operating side too, building process, accountability, and handoffs when the company needed structure.

AI systems builder

I build AI agent workflows for real work, then put governance and verification around them so the system does not drift.

Engagement shape

Start practical, then keep the relationship close enough to prevent drift.

1

Assessment and decision map

I map systems, risks, owners, and constraints so we can see what matters before anyone spends money.

2

Implementation sprint

I help plan, build, migrate, integrate, document, and test the parts that are creating drag right now.

3

Ongoing fractional partner

I stay close enough to help the work hold as a long-term partner through decisions, delivery, and handoff.

Next step

If your systems are starting to limit the business, I can help you get them back under control.

The first conversation is simple: we talk about the constraint, the risk, and whether a fractional CIO partner is the right shape of help.

Voice check: mechanical triads reviewed; paragraphs kept short; no em dashes in public copy.