IT strategy and fractional-CTO advice in Chicago

001/ Deliverables5 parts · 1 plan

• Technology roadmapwhat to buy, fix and retire, in order
• Vendor & software selectionrequirements, shortlist, recommendation
• IT budgetcosts and timing, month by month
• Security baselinethe essentials, checked and documented
• Fractional CTOsenior advice on a flat monthly retainer
• Systems inventoryevery tool you pay for, and who owns it

Most businesses we meet didn’t choose their technology so much as accumulate it: a tool for each new problem, a subscription someone signed up for in 2019, a server nobody wants to touch. An IT strategy turns that into a list of decisions, in order, with costs — written so an owner can act on it without a translator.

Illustration of the format — every roadmap is built from your own systems and priorities.

We build it from interviews with the people doing the work, an inventory of every system and subscription, and a look at where time and money leak today. Each item is ranked by impact, effort and risk, so the order is defensible — not just the loudest request. Read why every small business needs an IT roadmap for the longer argument.

Vendor and software selection

We define requirements with your team, shortlist 2–4 options, run demos against your real scenarios, check contracts and total cost, and recommend one in writing.

1. Requirements

   What the software must do, written with the people who’ll use it — and what it doesn’t need to do.

2. Shortlist

   2–4 realistic options, including “keep what you have” when that’s the honest answer.

3. Demos & contracts

   Vendors demo your scenarios, not theirs. We read the contract and total three-year cost.

4. Recommendation

   One written recommendation with reasons, risks, and a rollout plan.

Typical choices we help with: CRM (see comparing CRM software), Microsoft 365 vs Google Workspace, accounting and ERP, phone systems, and whether a custom tool beats another subscription. Our guide to evaluating IT vendors covers what to ask.

IT budgeting: costs and timing

We turn the roadmap into a budget: what you spend today on subscriptions, hardware, services and people, what each roadmap item will cost, and when the money is needed — so technology spend stops being a surprise.

The budget separates one-time project costs from recurring ones, flags renewals before they auto-renew, and shows which items pay for themselves by replacing something else. It’s built to be updated each quarter, not filed away. More in our article on IT budget planning.

• Multi-factor authenticationon email, finance, and every admin account
• Managed devicesupdates, encryption, remote wipe
• Tested backupsrestored at least once, not just running
• Email protectionfiltering, SPF, DKIM and DMARC
• Least-privilege accesspeople get what their job needs
• Written incident planwho to call, in what order

We check what you have, close the gaps together with your IT provider, and document the result in plain English. It won’t make you unhackable — nothing does — but it closes the gaps behind most small-business incidents. Our cybersecurity checklist is a good self-check before we talk.

Fractional CTO: senior advice without a full-time hire

A fractional CTO gives you senior technology leadership for part of each month on a flat monthly retainer — typically $2,000–$6,000 a month — instead of a full-time executive salary.

• Monthly planning sessionroadmap progress and next decisions
• Vendor calls & contractswe’re in the room, on your side
• Project oversightSalesforce, custom builds, migrations
• Quote and proposal reviewis this price and scope reasonable?
• Leadership updatesplain-English status for owners and boards
• On call for decisionsa quick answer before you sign

It’s a good fit when technology decisions keep landing on an owner or office manager who has a different day job. We coordinate with your managed IT provider rather than replacing it — see managed IT vs in-house IT vs fractional CTO for how the roles fit together.

Typical ranges, not quotes. Timelines are estimates and subject to change based on scope.

1. Interviews

   Short conversations with owners and the people doing the daily work.

2. Inventory

   Every system, subscription, device type and vendor — and who owns each.

3. Plan

   The prioritized roadmap, budget and security baseline, in writing.

4. Readout

   We walk leadership through it and agree what happens first.

How we make these decisions ourselves

We run five live software products, so we make the same buy-vs-build, hosting and vendor decisions we advise on — and live with the results. Here are the real choices behind our own products.

The pattern is the one we recommend to clients: buy the commodity, build what makes you different, keep the number of moving parts small, and write down why. See the products themselves on our products page.

• Nobody can list every subscriptionor who has the admin password
• The same data is typed twiceCRM, accounting, spreadsheets
• Renewals surprise youand costs creep up each year
• One person holds it all togetherand they’re thinking of leaving
• A security questionnaire arrivedfrom a customer or insurer
• Staff use AI with no rulesand nobody has decided what’s allowed

If three or more of these sound familiar, a roadmap will pay for itself. Our article on signs you’ve outgrown your technology goes deeper, and how to choose an IT consulting partner helps you compare us with others.

Who it’s for

IT strategy is for owners and leaders of small and mid-size businesses who make technology decisions without a CTO — and want someone senior, independent and plain-spoken on their side.

• Owner-led businesseswhere tech decisions land on the owner
• Growing teamswhose tools were chosen for a smaller company
• Companies with an MSPwho need strategy, not more tickets
• Leaders facing a big decisionCRM, ERP, a custom build, a migration

Where the plan points to Salesforce, we can start with a Salesforce health check; where it points to people and AI, with an AI acceptable-use policy and training.