The Winkler Group Llc

What The Winkler Group Llc does

The Winkler Group LLC is a private boutique law firm headquartered in Schaumburg, Illinois, founded by Thomas W. Winkler, who has practiced law continuously since 1982, with the LLC entity formed in 2008. The firm provides five core practice areas: Transactional & Commercial law, Real Estate, Property Tax Appeals, Trusts/Estates/Probate, and Banking & Financing. Its client base consists of small-to-mid-sized businesses, mid-market commercial entities, and medium-to-high-net-worth individuals, with operating geography centered in Illinois and adjacent Wisconsin via the founder's Wisconsin bar admission.

The firm is staffed by a small team comprising two primary attorneys (Thomas W. Winkler and Mehreen M. Rajabali, the latter licensed in Illinois and Texas), a third attorney (John B. Sprenzel, licensed in 2009), and a paralegal (Maggie Anderson). The firm's distinguishing technical capability rests on founder Thomas Winkler's dual Attorney and CPA credentials, which underwrites its tax-aware transactional, banking, and property tax work. No technology platform, automation infrastructure, or AI tooling is described beyond unspecified "proprietary systems" for document preparation.

The business model is fee-for-service legal representation with no publicly disclosed alternative fee arrangements, subscription pricing, or volume tiers. Go-to-market relies entirely on professional referral networks — attorneys, accountants, financial advisors, lenders, and bankers — supplemented by external reputational signals such as Illinois Leading Lawyers (a designation held by less than 5% of Illinois attorneys) and Avvo/lawyer rating profiles. There is no evidence of marketing investment, business development hires, or growth-oriented client acquisition infrastructure, and the firm shows no signs of operating as a venture-backed or roll-up-oriented practice.

Name

The Winkler Group Llc

Legal name

THE WINKLER GROUP LLC

Website

https://winkler-law.com

Company type

Private

Founded year

2008

Operating status

Operating

Headcount range

1–10 employees

Short description

The Winkler Group LLC is a Schaumburg, Illinois-based boutique law firm delivering transactional, real estate, property tax, trusts/estates, and banking legal services to small and mid-sized businesses and high-net-worth individuals across Illinois and Wisconsin.

Ownership category

akta.pro rank

Product category

Legal Services

NAICS

Offices of Lawyers (541110), Legal Services (5411)

SIC

Services-Legal Services (8111)

akta.pro primary industry

Family & Private Client (Trusts & Estates) Law (BPAHAAAK)

Keywords

• Commercial real estate law
• Estate planning services
• Business transaction law
• Property tax appeals
• Banking financing law

Headquarters

HQ city

Schaumburg

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure

Revenue model

1. Legal Services Fees: The firm generates revenue through legal service fees for representation in transactional, commercial, real estate, estate planning, banking and financing matters. Services are provided to businesses ranging from sole proprietorships to companies valued at around $100 million.

Pricing tiers

Go-to-market motion1 record

Distribution channels1 record

Marketing channels4 records

Core offering

The Winkler Group LLC is a Schaumburg, Illinois-based boutique law firm providing transactional, commercial real estate, banking and financing, property tax assessment appeal, and trusts/estates/probate legal services. Founded in 2008 by Thomas W. Winkler (Attorney at Law and CPA), the firm serves small and mid-sized businesses and high net worth individuals. The practice combines legal counsel with the founder's CPA background to advise on business transactions and tax matters.

Product overview

The Winkler Group LLC is a law firm offering personalized legal representation through five distinct practice areas: Transactional & Commercial, Commercial & Industrial Real Estate, Property Tax Assessment Appeals, Trusts & Estates, and Banking & Financing services. The firm serves entrepreneurial individuals and small-to-mid-sized businesses with a team of attorneys and staff, emphasizing accessibility, cost-efficiency, and customized solutions tailored to each client's specific needs and concerns.

Differentiator

Problem solved

Functional benefit

Products and services

• Transactional & Commercial Law

Quantifiable outcome

• 35+ years of Illinois legal experience
• +1 more outcomes

Named customers4 records

Segments4 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature2 records

Partnerships

Nine partnerships are on record, tiered core and minor.

• Accountants/CPAscoreStrategic or Co-development PartnerProfessional affiliations with accountants and CPAs for coordinated client service, particularly in estate planning, business succession, and tax-related matters.
• Business BrokerscoreStrategic or Co-development PartnerProfessional affiliations with business brokers for business transactions, mergers and acquisitions, and business succession planning.
• Real Estate BrokerscoreStrategic or Co-development PartnerProfessional affiliations with real estate brokers for commercial and industrial real estate transactions and property tax matters.
• Title Insurance CompaniescoreStrategic or Co-development PartnerProfessional affiliations with title insurance companies for real estate transactions.
• Investment AdvisorscoreStrategic or Co-development PartnerProfessional affiliations with investment advisors for coordinated wealth management and estate planning services.
• Personal & Business BankerscoreStrategic or Co-development PartnerProfessional affiliations with bankers for banking and financing transactions, loan documentation, and commercial lending matters.
• Civil Engineers & SurveyorsminorOthersProfessional affiliations with civil engineers and surveyors for real estate development and transaction support.
• Environmental EngineersminorOthersProfessional affiliations with environmental engineers for property assessments and due diligence.
• Trust OfficerscoreStrategic or Co-development PartnerProfessional affiliations with trust officers for estate administration and trust management services.

Scale indicators2 records

Recent moves4 records

Expansion highlights4 records

Direct peers

• Robbins Schwartz: Illinois-based law firm serving businesses, municipalities, and individuals with commercial real estate, corporate, banking, and trusts/estates practices. Strong geographic and practice-area overlap with The Winkler Group.
• Rathje Woodward LLC: Wheaton, Illinois-based law firm serving closely-held businesses and individuals with real estate, business transactions, estate planning, and banking practices. Most comparable in size, geography (Chicago western suburbs), and client profile to The Winkler Group.
• Much Shelist, P.C. Chicago-based business law firm serving closely-held businesses, entrepreneurs, and emerging companies. Practice areas overlap directly with The Winkler Group's transactional/commercial, real estate, and M&A work for similar client profiles.
• Aronberg Goldgehn Davis & Garmisa: Chicago-based mid-sized business law firm practicing in closely-held business, real estate, banking, and trusts/estates matters for middle-market companies and individuals. Comparable practice composition and client base.
• Momkus LLC: Small DuPage County/Chicago suburb law firm focused on business transactions, real estate, estate planning, and banking matters for closely-held businesses and entrepreneurs. Closest peer by size, geography, and practice mix.

Broad incumbents

• SmithAmundsen LLC: Larger full-service Illinois law firm with business transactions, real estate, banking, and trusts/estates practices. Serves a similar mid-market and entrepreneurial client base across the Chicago metro and broader Midwest.
• Barack Ferrazzano Kirschbaum & Nagelberg LLP: Established Chicago business law firm with commercial real estate, banking, corporate transactions, and trusts/estates practices. Comparable focus on mid-market businesses and closely-held companies, but with significantly more attorneys and resources.
• Levenfeld Pearlstein LLC: Mid-sized Chicago-based business law firm with closely-held business, real estate, and trusts/estates practices. Comparable practice mix serving entrepreneurial and mid-market clients in Illinois, though materially larger in scale than The Winkler Group.

Regional players

• Kelley Kronenberg: Multi-office business and commercial law firm with real estate, business transactions, and banking practices serving closely-held businesses. Similar practice areas to The Winkler Group but operating in different geography (Florida and other markets).

Others

• Resolute Legal PLLC: Technology-enabled legal services provider serving real estate investors and small businesses with transactional, property tax, and entity formation matters. Not a direct competitor, but representative of the technology-enabled disruption potentially impacting The Winkler Group's template-based differentiation in coming years.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat3 records

Key risks5 records

Key highlights6 records

Customer concentration

• LinkedInlinkedin.com/company/the-winkler-group-llc

Revenue estimate

Valuation estimate

Number of profiles

Profiles4 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about The Winkler Group Llc