Chicagoland's Trusted Bookkeeping Partner

You've Built Something
Worth Protecting.
Your Books Should
Reflect That.

Expert bookkeeping and financial operations for Chicagoland businesses at $1M+ in revenue. Local team. Flat-rate pricing. Real results.

US-Based Expert Team
Flat-Rate, Transparent Pricing
Local Chicagoland Team — Not a Call Center
Trusted by Growing Businesses
Chicago skyline
Sound Familiar?

Your Business Has Grown.
Your Bookkeeping 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 Bookkeeper Is Overwhelmed — or Overstepped

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 bookkeeping 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
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
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 Bookkeeping, 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.

1

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.

2

We Manage the Work — You Stay in the Loop

Our team handles your day-to-day bookkeeping: transaction categorization, reconciliations, AP/AR, payroll coordination, and month-end close. You'll have a dedicated point of contact who knows your file.

3

Monthly Review Calls Keep You in Control

Every month, you sit down with your bookkeeper for a financial review. We walk through your numbers, flag anything that needs attention, and make sure you're always looking ahead — not scrambling to catch up.

The Essentials Package

Accurate, timely bookkeeping 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
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.

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.
Industries We Serve

Serving Chicagoland Businesses Across Industries

Our team brings deep, industry-specific experience — not one-size-fits-all bookkeeping. 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.

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.

L
Leslie Kischer G Google Review

We love our bookkeeper Patty! She did an amazing job cleaning up our books. They were an absolute mess! Even my new accountant was very impressed. He said it made his job easier. Patty is also very professional, friendly, and great with communication. We're so glad we connected with Julyn, the marketing professional because she did a great job helping us identify what we needed and assisted with a seamless onboarding. Thank you Supporting Strategies — I highly recommend!

J
Jennifer Dexter G Google Review · Local Guide

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!!!

M
Maria Vasos G Google Review
Where We Work

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.

Arlington Heights Buffalo Grove Burr Ridge Deerfield Des Plaines Evergreen Park Evanston Frankfort Glencoe Highland Park Inverness Joliet Kenilworth Lake Forest Lincolnshire Morton Grove Mount Prospect Northbrook Orland Park Palatine Park Ridge Rosemont Skokie Vernon Hills Wheeling Winnetka And more…

Lynette and George together serve businesses across the full Chicagoland metro — from the North Shore and Northwest Suburbs to the Southland and Southwest. Wherever you're located, you'll work directly with a local team that knows your market.

Why Supporting Strategies

Built for Business Owners
Who Are Done Settling

There is no shortage of bookkeepers. There is a shortage of bookkeeping partners who think ahead, communicate clearly, and actually care about your business.

All U.S.-Based Team

Every member of our team is U.S.-based. No offshore contractors, no call centers. When you reach out, you're talking to someone who understands your business environment.

10+ Years Average Experience

Our team averages over a decade of real-world accounting and bookkeeping experience — so your books are handled by professionals who have seen every scenario, not junior staff learning on the job.

Degree-Qualified Staff

Every associate holds a bachelor's degree in accounting or a related field. Many hold advanced degrees or CPA credentials. You're not hiring a generalist — you're hiring a specialist.

Built-In Backup Coverage

Our cross-trained team model means your books are never held hostage by one person's vacation or departure. Continuity is built into how we operate — not something you have to worry about.

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.

Relational, Not Transactional

We're your financial operations partner, not a vendor. Your dedicated team knows your business, picks up the phone when you call, and brings you solutions — not just reports.

Free Resource

Is Your Bookkeeping Ready for the Next Level?

Download the Bookkeeping Health Checklist — a practical, no-fluff assessment for businesses generating $1M or more in revenue. In 10 minutes, you'll know exactly where your financial operations stand and where the risks are hiding.

  • The 12 signs your bookkeeping is holding your business back
  • Month-end close checklist — what should be happening and when
  • The questions you should be asking your bookkeeper (but probably aren't)
  • Red flags that signal it's time to make a change
  • A simple scorecard to grade your current financial health
Free Download
Bookkeeping Health Checklist for $1M+ Businesses
  • 12 signs your books are holding you back
  • Month-end close checklist
  • Financial health scorecard
  • Red flags & action steps
Get Instant Access — It's Free
Fill out the form below and we'll send the checklist straight to your inbox.
Based in Chicagoland. Available when you need us.

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Let's Talk

Your Business Has Outpaced
Reactive Bookkeeping.
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.

Proudly serving Chicago's northwest suburbs, the greater Chicagoland metro, and surrounding communities.

Book My Free 15-Minute Call