FINANCIAL OPERATIONS & Accounting Services for Growing Chicagoland Businesses
You've Built Something Worth Protecting. Your Books Should Reflect That.
Supporting Strategies provides expert accounting and financial oversight to businesses generating $1M or more in revenue — so you can stop worrying about your numbers and get back to running your business.
✓ US-Based Expert Team | ✓ Flat-Rate, Transparent Pricing | ✓ Dedicated to Chicagoland Businesses | ✓ Serving 200+ Clients Nationwide
Your Business Has Grown.
Your Accounting Hasn't Kept Up.
You're not alone. Most businesses at your stage hit the same wall — and the cost of staying stuck is higher than you think.
You're Managing Finances by Feel
You know roughly where the money is. But you don't have real-time visibility into your cash position, your margins, or what's coming next quarter. You're making decisions on instinct instead of data — and it's starting to cost you.
Your Current Accounting Resource Is Overwhelmed
Whether it's a part-time hire, a family friend, or a solo accountant who's stretched too thin, you've felt the cracks. Month-end closes are late. Reports are inconsistent. You're not sure you can trust what you're seeing.
Your Growth Deserves Better Infrastructure
At $1M+ in revenue, your financial operations need to match the ambition of your business. Reactive accounting isn't just inefficient — it creates risk. You need a team, a process, and a system that scales with you.
This is exactly the problem Supporting Strategies was built to solve.
YOUR LOCAL TEAM
Meet Lynette & George
Two experienced Managing Directors. One Chicagoland team. When you work with Supporting Strategies, you work directly with people who are invested in your business - not handed off to a call center.
Lynette DeRose
Managing Director - Chicago Southland
BS in Accounting, Calvin College
20+ years in operations & finance
Expertise in commercial real estate & managed IT
Founded SS Chicago Southland, 2018
George Stephen
Managing Director - Northern Chicago
- MBA, Warwick Business School London
- BS Economics, University of Illinois
- 20+ years leading startups & high-growth companies
- Founded SS Northern Chicago, 2018
How It Works
Expert Outsourced Accounting, Built Around Your Business
We handle the day-to-day financial operations so you have accurate books, clean data, and a team that actually picks up the phone.
We Learn Your Business
Your engagement starts with a thorough onboarding — we get to know your accounts, your processes, your pain points, and your goals. No cookie-cutter setup. Your books are managed the way your business actually operates.
We Manage the Work — You Stay in the Loop
Our team handles your day-to-day accounting: transaction categorization, reconciliations, AP/AR, payroll coordination, and month-end close. And we don't disappear after setup — you'll have a dedicated point of contact who knows your file.
Monthly Review Calls Keep You in Control
Every month, you sit down (virtually) with your Accounting Team for a financial review. We walk you through your numbers, flag anything that needs attention, and make sure you're always looking ahead — not scrambling to catch up.
Supporting Strategies is not a CPA firm and does not provide tax preparation, tax advisory, or attestation services. For tax-related needs, we are happy to work alongside your existing CPA or provide a referral.
The Essentials Package
Accurate, timely accounting and a complete month-end close process — giving you the financial clarity and dependable foundation required to manage your operations with confidence. Choose the tier that fits your business.
CORE
Peace of mind that your books are up-to-date, accurate, and properly maintained.
- Weekly cash & credit card transaction categorization & processing
- Full accrual-based month-end close process
- Monthly financial review call
FULL
Gain additional data and details in a monthly accounting review of the numbers.
- Everything in Core
- Daily cash & credit card transaction processing
- Deeper monthly accounting review & analysis
COMPLETE
Get more value and insights from your financial data via complex tracking and management.
- Everything in Core & Full
- Class, location & customer tracking
- Job costing
- Grant accounting
- Multi-entity & consolidations
- Inventory, multi-currency, IOLTA & more
Pricing is customized to your business. Supporting Strategies also offers Insights, Compliance, Revenue, Expenses, and People service areas — including controller-level and fractional CFO services. Ask us what's right for your stage of growth.
INDUSTRIES WE SERVE
Serving Chicagoland Businesses Across Industries
Our team brings deep, industry-specific experience — not one-size-fits-all accounting. We understand the nuances of your sector because we've worked in it.
Commercial Real Estate
Law Firms & Trust Accounting
Nonprofits & Fund Accounting
Healthcare Practices
Technology Companies
Construction & Trades
Light Manufacturing
Retail & Wholesale
What Our Clients Say
Real Businesses. Real Results.
Supporting Strategies serves 200+ clients nationwide. Here's what growing business owners say about working with us.
Supporting Strategies has been a great partner in helping us streamline our accounting practices. Their expertise and willingness to learn our processes has been incredibly valuable.
Hired SS Southland to handle the bookkeeping for our law firm after firing another outside bookkeeper for lack of performance. SS really stepped up and not only has done their job timely and efficiently, but also found and fixed mistakes from the prior bookkeeper. Highly recommend!!!
Excellent expertise and knowledge! The team at Supporting Strategies is responsive and efficient. Highly recommended!
Serving Communities Across Chicagoland
Lynette and George both serve businesses across the entire Chicagoland area. No matter where you're located, you're getting a local team — not a call center.
WHY SUPPORTING STRATEGIES
Built for Business Owners Who Are Done Settling
There is no shortage of bookkeepers. There is a shortage of financial operations partners who think ahead, communicate clearly, and actually care about your business.
A Real Team, Not a Solo Act
Every client is supported by an expert team — not one person who calls in sick. You get consistency, depth, and a bench that scales as you do.
Flat-Rate Pricing. No Surprises.
You know what you're paying before the month starts. No hourly billing. No scope creep invoices. Just straightforward, value-based pricing built around your business.
Monthly Review Calls — Included
We don't just send reports and disappear. Every month, you sit down with your Accounting Team to review your numbers, ask questions, and plan ahead. Proactive, not reactive.
US-Based Experts Only
Your books are handled by experienced, US-based accountants — not offshore contractors. Real expertise, real accountability, real communication.
Technology That Works for You
We work within your existing tech stack or help you build one. QuickBooks, Xero, Bill.com, Gusto — we know the tools and know how to use them right.
Relational, Not Transactional
We're not just processing transactions — we're your financial operations partner. You get a team that remembers your business, understands your goals, and picks up the phone when you call.
FREE RESOURCE: The Month‑End Benchmark Report
The Month‑End Benchmark Report — Self‑Assessment for $1M+ growth‑stage Chicagoland businesses
This free self‑assessment diagnostic walks through the key benchmarks of a healthy financial operation — from close timelines and cash flow visibility to controller-level oversight and reporting accuracy — and lets owners identify exactly where their current setup is falling short. Connect with Lynette and George at Supporting Strategies Chicagoland for a no‑pressure conversation to discuss your results.
Get Instant Access — It's Free
We'll send you the report via email.
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Lynette DeRose — Managing Director
Supporting Strategies Chicago Southland
George Stephen — Managing Director
Supporting Strategies Northern Chicago
Let's Talk
Your Business Has Outpaced Reactive Accounting. Let's Build Something Better.
If your revenue is at $1M or above and your financial operations aren't keeping pace, this is the conversation you've been putting off. It's a 15-minute call — no pressure, no pitch. Just an honest conversation about where you are and whether we're the right fit. We work with a limited number of clients at a time so that everyone gets the attention they deserve. If you're curious, the best time to reach out is now.
Supporting Strategies Chicagoland
Serving the Greater Chicago Metropolitan Area
GET IN TOUCH
Lynette DeRose
George Stephen
Supporting Strategies — Chicagoland is a licensed franchise of Supporting Strategies, LLC. Supporting Strategies is not a CPA firm and does not provide tax preparation, tax filing, tax advisory, audit, or attestation services. © 2026 Supporting Strategies — Chicagoland. All rights reserved.