Bookkeeping built for
Chicago businesses.
AI-powered, expert-reviewed bookkeeping for Chicago businesses of every size — from solo founders and corner shops to multi-location restaurants, growing manufacturers, finance firms, and logistics operations. Same dedicated team, same Portal, same monthly close.
From the trading floor
to the loading dock.
Chicago runs on more than one industry, and at every size — from solo operators and one-location shops to mid-market manufacturers and trading firms. We've handled books for them all, including the Illinois-specific quirks the national firms miss.
Finance & FinTech
Trading desk reconciliation, FCM accounting, prop firm books, futures/derivatives margin tracking. Built for Chicago's trading and FinTech ecosystem.
Prop · brokerage · FinTechManufacturing & Industrial
Job costing, materials vs. labor, COGS rollups, multi-state sales tax for shipping. From small machine shops to mid-sized industrial operations.
Job costing built-inReal Estate
Property-level books, syndications, K-1 distributions, depreciation schedules. From single-property LLCs to Cook County multi-entity portfolios.
Multifamily · commercial · STRRestaurants & Hospitality
Daily sales reconciliation, food cost tracking, tip pooling, multi-location rollups. From West Loop tasting menus to Lincoln Park neighborhood spots.
Multi-location readyLogistics & Distribution
Multi-state nexus, freight expense allocation, fuel tax, fleet depreciation, warehouse cost rollups. Built for Chicago's role as the country's freight hub.
Multi-state freight readyProfessional Services
Trust accounting, retainer recognition, partner draws — built for law firms, consultancies, and agencies across the Loop, River North, and Fulton Market.
Law · consulting · agenciesLive in 14 days.
Reviewed every month.
No 90-day onboarding nightmare. No mystery process. Here's exactly what working with us actually looks like.
Discovery call
30 minutes. We review your current setup, walk you through the Yesler Portal, and quote a clear monthly engagement scoped to your business — before any work begins.
Onboarding
We connect to your bookkeeping software (or set you up fresh in QuickBooks/Xero), build your Portal, and your dedicated Illinois-savvy team learns your business. Live in 14 days.
Monthly close, 3-tier review
AI handles the first pass. Your dedicated specialist reviews and catches edge cases. Senior management or our in-house CPA signs off. You see every step in the Portal.
Everything Chicago businesses need.
Pick one. Bundle them all. Most clients combine monthly bookkeeping with payroll, Illinois sales tax filings, and annual replacement tax.
Monthly Bookkeeping
Categorization, reconciliation, clean reports — done in QuickBooks, Xero, FreshBooks, or Wave.
Payroll
W-2, 1099, multi-state for remote teams. Illinois-specific compliance (PFML, unemployment) handled.
Illinois Sales Tax
Chicago's 10.25% stack (state + county + city + RTA) tracked and remitted correctly. Multi-state if you ship out.
Tax Prep + Annual Report
Federal returns, K-1s, 1099s. IL Annual Report & Personal Property Replacement Tax filed on time.
Tax Planning
Year-round strategy to reduce liability — entity structure, S-corp elections, retirement plans.
Catch-Up Bookkeeping
Six months behind? Twenty-four? We've seen worse. We'll get you current and audit-ready.
Illinois-aware bookkeeping.
Real humans on every account.
National firms treat you like a number. Small local shops disappear when their one bookkeeper takes vacation. We're built differently.
Illinois-specific expertise
We handle Illinois Annual Report filings with the Secretary of State, navigate Chicago's 10.25% sales tax stack (state + county + city + RTA), manage Personal Property Replacement Tax (PPRT) for corporations and pass-throughs, and understand Cook County's specific business taxes and reporting that catch national firms off-guard.
Three layers of review on everything
AI handles the repetitive work. Your staff specialist checks it and handles edge cases. Senior management or our in-house CPA signs off before anything is finalized. No single point of failure, no "trust us" black box.
Multi-platform specialists
QuickBooks Online & Desktop, Xero, FreshBooks, Wave, Sage. We work where you already do — your books stay where your CPA, lender, and tax software expect them.
Central business hours
Your dedicated team is available during CST. Same-day responses on weekday messages. No outsourced call centers, no 3am email chains.
Right-sized for your business — and scales with you
Whether you're a one-person shop, an owner-operator with a small team, or a multi-entity company outgrowing your last firm, we scope every engagement to where you actually are. As you grow, your team stays the same — we scale alongside you instead of handing you off to a different tier.
Built to scale with your business.
Whether you're a solo founder finally getting your books in order or a multi-entity company outgrowing your last firm — we'll show you what life looks like with Yesler running your back office.
- Same dedicated team as you grow
- Free Portal walkthrough
- Month-to-month, cancel anytime
- Books stay in your software
We're a Loop-based consulting firm that grew from 3 to 22 people in 18 months. Our old bookkeeper couldn't keep up — and didn't understand Illinois replacement tax or Chicago's sales tax stack. Yesler took over, and our quarterly cleanup nightmare became a non-event. Their Portal means I actually know what's happening with our finances now.
Questions Chicago business owners ask.
Honest answers to what we hear before every demo.
Are you actually based in Chicago?
Do you handle Illinois Annual Report and replacement tax filings?
We're a prop firm / trading shop — can you handle the complexity?
How does Chicago's sales tax stack actually work?
We're already in QuickBooks Desktop — is that a problem?
I'm a solo founder / small business — am I the right fit?
How fast can you actually start?
Ready to get your Chicago books in order?
Tell us about your business. We'll show you what life looks like with an Illinois-aware bookkeeping team running your back office — built for businesses of every size, from solo founders to multi-entity companies.