Fractional CFO & Controller Services for Chicago Businesses

Chicago companies rarely fail from lack of work. They fail from the distance between when the work is done and when it is paid, stretched over a winter that does not care. A $10 million concrete contractor in Aurora does 70 percent of its revenue between April and November and carries a union crew, an equipment fleet, and a shop lease through the rest. A $6 million distributor in Schaumburg has the mirror problem: customers who order in the spring and pay in the summer, and a supplier who wants the pre-season inventory paid for in March. A professional-services firm in the Loop has no season at all, just a 90-day receivable cycle and a rent bill.

The symptoms repeat across the metro. Receivables age past 75 days while the line of credit covers payroll. Change orders were performed on a field directive and never priced. Retainage from a job that finished in October is still on the balance sheet in May. The surety asks for a WIP schedule that reconciles to the ledger and gets a spreadsheet that reconciles to a memory. The Chicago general contractor license class was set when the company was half its current size, and the next bid exceeds it. And every controller worth hiring already has an offer from a hospital system, a bank, or a manufacturer in the suburbs.

The fix is a sequence rather than a hire. Assess what is true about cash, margin, and debt. Clean up the ledger so the numbers can be believed. Stabilize the weekly cash cycle and the monthly close. Document the process so it survives without us. Then transition it to your team or to a full-time hire when the company can support one. That sequence is how a $5 million company becomes a $20 million company without the back office becoming the reason it stalls, and how a company survives its third winter as comfortably as its first.

Our clients are privately held companies between roughly $3 million and $50 million in revenue, owned by the people who run them. In Chicago that means general contractors and construction managers working the city and the collar counties, mechanical, HVAC, electrical, and plumbing contractors with union crews across Cook and DuPage, paving, concrete, and site contractors in Will and Kane, specialty trades in masonry restoration and curtain wall, and the building-materials distributors and equipment dealers in Elk Grove Village, Bedford Park, and along I-55 that serve them.

We also work with the middle-market companies Chicago is built on: light manufacturers and metal fabricators in the industrial corridors, food and beverage producers, wholesale distributors, logistics and trucking operators near the intermodal yards in Joliet and Elwood, professional-services firms, medical groups, and the property-management and real estate operating companies that live on the same slow receivable cycle. The situations repeat: the owner still approves every check and reads cash from the bank app; the controller retired, or was really a bookkeeper with a title; the bank wants a monthly package and a covenant certificate and receives neither; a sale, a partner buyout, or a second-generation transition is coming and the books would not survive diligence; or cash is short and the winter is long.

You should hire someone else if you need bookkeeping alone, tax preparation, an audit opinion, or legal advice. We coordinate with your CPA and your attorney and we stay in our lane. If your plan is to hire a full-time CFO and hope the ledger fixes itself, we will talk you out of it on the first call, at no charge, which is more than the last consultant did.

A fractional CFO gives you the judgment of a chief financial officer for a fraction of the week and a fraction of the cost. For a Chicago company that means a 13-week cash forecast updated every Monday that reflects the actual pay-application calendar, the actual retainage schedule, and the actual union remittance dates; a bank relationship managed with a monthly package instead of an annual scramble; and pricing, bidding, and hiring decisions made with margin data by customer instead of by instinct. The national fractional CFO page covers the full scope. This page is about how it works between the lake and the collar counties.

Chicago lenders and sureties have financed a century of building cycles and they underwrite accordingly. A contractor deciding whether to take a package on the 1901 Project, an O'Hare concourse, a Chicago Public Schools job, or a distribution center in Joliet needs to know before signing whether it can fund 90 days of labor and material ahead of the first pay application, and what a pay-when-paid clause and a lender's inspector do to that number in December. A manufacturer deciding whether to add a second shift needs to know what the shift has to produce to pay for itself. Those are CFO questions. We answer them with a model, a bank conversation, and a decision, usually inside the same week.

Engagements start at $3,500 per month for a Fractional CFO and $8,500 per month for an Operating CFO who owns the finance function day to day. CFO Advisory starts at $5,000, Embedded CFO at $12,500, and interim leadership is custom. Those are starting points, not quotes. Final pricing reflects company size, entity count, transaction volume, the condition of the books, urgency, and what the bank, surety, and investors are asking for. Travel to Chicago is scoped in the engagement letter, and one-time cleanup and software are separate unless expressly included.

A controller makes the numbers true and on time. Ours close the month within 10 business days, keep a job-cost or product-cost ledger that ties to the general ledger, produce a WIP schedule the surety can read, run receivables and payables on a published calendar, and reconcile every bank, loan, and credit-card account monthly. For an Illinois contractor that includes retainage receivable by project, change-order billing with the directive attached, union remittance and certified payroll tracking, and the lien notice calendar that keeps rights alive on every job where you are not the prime.

In Chicago the hard part is not the work. It is finding someone who can do it and keeping them through the next recruiter call from a hospital system, a bank, or a manufacturer in Lake County. A $10 million subcontractor in Cicero cannot win that contest on salary. A fractional controller solves the retention problem by running the function remotely and documenting it, so the next hire inherits a process instead of a mystery. We work in QuickBooks, Sage 300 CRE, ServiceTitan, JD Edwards, and Power BI, which covers most of what is installed between Evanston and Orland Park.

Controller engagements start at $2,500 per month. The scope is written down on day one, the close calendar is published, and the deliverables are the same every month: financial statements, job or product reports, WIP, aging, and a cash position you can read in five minutes on the Metra. When the company is ready for a full-time controller, the documented process goes with the job. Fix it. Run it. Document it. Hand it off.

Illinois does not license general contractors at the state level. Plumbing contractors are licensed by the Illinois Department of Public Health and roofing contractors by the Department of Financial and Professional Regulation, and everything else is municipal. The City of Chicago licenses general contractors in five classes by single-contract value: Class E up to $500,000, Class D up to $2 million, Class C up to $5 million, Class B up to $10 million, and Class A with no limit. A growing contractor that wins a $3 million package on a Class D license has a problem the estimator did not price. We track the license class, the insurance certificates, and the suburban registrations per entity inside the close checklist, so the class is raised before the bid rather than after the award.

The Illinois Mechanics Lien Act has its own calendar. A subcontractor or supplier generally serves a notice of its lien claim on the owner within 90 days of its last day of work or delivery, and a lien is recorded within four months of completion to be effective against later purchasers and lenders. Public work substitutes bond claims and their own notices. None of that is legal advice, and we do not give it. What we do is build the notice calendar into the billing process so the same person who issues the pay application confirms the notice went out, and your construction attorney is called before a deadline rather than after one. Our principal has managed mechanic's liens, claims, and litigation support coordination for multi-entity contractors.

Surety capacity in Chicago rests on financial statements a bonding company can trust: a WIP schedule that reconciles to the ledger, consistent gross margins by job, working capital that is real at year end, and an owner who can explain the numbers. Chicago Public Schools, the Public Building Commission, the Tollway, and the airport program all require bonds, and the surety's appetite is set by your last statement. A construction CFO builds the package the surety wants and keeps it current so the next bid is not held up by the last close. Milwaukee contractors work under a different licensing regime with the same surety questions, and the process travels.

Trouble in Chicago usually arrives in February. The line of credit that was supposed to come down in December is still fully drawn. The last pay application of the season is stuck behind a lender's inspection that will not happen until the snow melts. Union benefit remittances slip a month, and the fund's auditors will notice before the bank does. Payroll taxes slip a quarter. The supply house moves the account to COD. The owner has been funding payroll from savings since Thanksgiving and calls it seasonal. None of that is fatal if someone takes control of cash in the next two weeks.

We start with a 13-week cash forecast built from the actual receivables, the actual payables, the actual payroll, and the actual remittance schedule, not the budget. Then vendor triage: who gets paid, when, and what they are told, in writing. Then a lender conversation with a plan attached, because banks extend patience to borrowers who show up with numbers and a calendar. The principal has led finance through a Chapter 11 process, including debtor-in-possession operations and court-required reporting, so nothing on the list will be the first time. Our turnaround CFO and 13-week cash-flow forecast pages cover the mechanics.

The 2026 cycle in Chicago is uneven. A handful of very large projects are absorbing labor and bonding capacity while suburban commercial and some manufacturing work has slowed, unemployment has drifted up, and the county keeps losing residents on net. A site contractor that lived on suburban retail is resizing at the same time a curtain-wall sub on the West Side is turning down work. Both need the same discipline: real margin by job, a cash forecast that goes past next Friday, and the resolve to stop taking work that loses money slowly. One of them is about to learn that its favorite customer was never profitable, and it is cheaper to learn that in a spreadsheet.

Seasonality is the first challenge and it shapes everything. An outdoor contractor in Chicagoland earns most of its revenue in about seven months and carries a 12-month cost structure, and the cash from the last good month arrives after the first bad one. Winter work, whether indoor fit-outs, plant maintenance, or snow removal, has to be priced to cover the fixed cost it is actually carrying, not the marginal cost the estimator prefers. We build the seasonal curve into the forecast, size the line of credit to the trough rather than the peak, and time equipment purchases so they do not land in the same month as the union true-up.

Union and public-work administration is the second. Certified payroll, prevailing wage, benefit remittances due on fixed dates, and the fund audits that follow are not optional and they are not forgiving. A contractor that slips a remittance to make payroll has borrowed from the people least likely to forgive it. We put the remittance calendar in the cash forecast alongside payroll and taxes, so the decision to delay anything is made on paper a month early rather than at the bank on a Thursday. The same discipline covers Chicago Public Schools, Tollway, and airport payment cycles, which run on their own schedules and their own paperwork.

Cost and transition round out the list. Illinois taxes, Cook County property costs, insurance, and the wage rates that come with a union workforce all belong in the job cost, not in overhead where they quietly eat the margin. And Chicago is full of second- and third-generation companies where the founder still signs every check and the succession plan is a handshake. Owners planning a family transition, a management buyout, or a sale need two years of clean statements before the conversation starts, and the buyers active in the Midwest middle market read every line. We build the reporting that makes the transition financeable and the company sellable, and we get the CPA in the room before year end rather than after it.

• Seasonal revenue curves and winter fixed-cost coverage built into pricing and the 13-week forecast
• Union remittance, certified payroll, and prevailing-wage calendars carried alongside payroll in the forecast
• Illinois lien notices and Chicago license classes tracked inside billing and the close checklist, in coordination with counsel
• Public-agency, construction-manager, and lender-inspection payment cycles modeled by customer
• Surety and bank packages built on a WIP schedule that reconciles to the general ledger
• Succession, buyout, and sale readiness built on two years of clean statements
• Controller retention answered with a documented, transferable process