Hire a Professional Business Broker in Chicago
Introduction
Why Hire a Business Broker?
Looking to sell your business in Chicago in 2025? Playbook Corporate Advisory, with over $100M in successful sales, offers expert business broker services to maximize your value and deliver a streamlined process at each step of your sale. From valuation to closing, our Chicago-based team ensures business owners a one-stop firm that can deliver the experience and know how to sell your business confidentially and successfully. Since our founding in 2016, Playbook has delivered results to many different industries including manufacturing, distribution, supply chain, technology, business services as well as retail and brick and mortar.
Expert Valuation: We provide accurate business valuations that reflect the current market trends and the unique aspects of your business. Business assets, working capital, vendor and customer contracts are all inputs to assess for proper valuations.
Confidentiality: We maintain the highest level of confidentiality, ensuring that the sale process does not disrupt your business operations or devalue your business. Our team will manage data rooms to secure your business information and secure NDA’s from all prospective parties.
Marketing Expertise: Our targeted marketing strategies are designed to attract qualified buyers quickly and discreetly. Our current database has over 10,000 active business buyers located not only in Chicago but nationwide. In 2025 our team has onboarded over 2569 new buyers that are actively searching to acquire companies. We leverage past listings to generate activity quickly and kick off marketing in the first week of going to market. (How to Sell in 120 days)
Negotiation Skills: With a wealth of experience in negotiating business sales, we strive to secure the best possible outcome for you. Price is important but so is deal structure. A recent client was able to generate an additional $195,000 in earnout payments in the first 12 months post closing. Another client leveraged a $250,000 holdback to earn an additional $750,000 in seller note payments.
Streamlined Process: We handle all aspects of the sales process, from initial listing to closing, ensuring compliance with all legal and financial requirements. Our firm has experienced 3rd party attorneys and quality of earnings professionals that can help you structure a deal that maximizes payments, post closing rep and warranties and tax allocations.
Our Business Broker Services
At Playbook Corporate Advisory, we offer a comprehensive range of services to facilitate the sale of your business:
Business Valuation:
Referrals to top nationwide approved SBA valuation firms that can give you a complete seller assessment of your business before you go to market. Learn about your operations from 3rd parties that prepare comprehensive valuation services for owners.
Market Analysis:
How does your company compare to the industry? What are the challenges you face in 2025-2026 with the advent of AI? How do buyers perceive your industry? Who are the likely buyers? Private equity? Individual buyers backed by SBA?
Where does your business get listed online? How does the broker protect confidentiality?
Buyer Screening:
Playbook Corporate Advisory has an active database of over 10,000 in their Hubspot database that is actively updated. In fact, we’ve added over 2600 buyers in 2025.
Due Diligence - Secure Data Rooms
Closure and Post-Sale Assistance
Active Professional Network of Transaction Attorneys, Lenders, Title Companies
Client Testimonials
Hear from some of our past clients who have successfully sold their businesses with our help:
Testimonial 1: "Jim demonstrated, with his perseverance and professionalism, how to successfully manage the sale of our company Comercializadora del Midwest (CDM Foods), overcoming all the typical challenges of a negotiation of this magnitude. After months of hard work, we happily closed the sale of our company. We are grateful to Jim for his dedication and effort, as he not only captured the client's interest in our company but also helped us achieve our ultimate goal: selling our company to a client who met all our expectations. We highly recommend Jim for his seriousness, extensive experience, and deep respect for both parties involved in the process.”
Roberto Gomez, President & Founder, Sold to Lipari Foods (Press Release)
Testimonial 2: "Jim made the process of selling my business easier than I could have ever expected. As a small business owner, the idea of selling something you have put everything into for several years can be daunting. Jim helped me through every aspect of the process from understanding what to expect, getting the most return on my investment, and helping me through some of the unexpected hurdles and concerns along the way. If you are considering selling your business don't try to do it on your own and I highly recommend Jim/ Playbook!”
Darren Seefeldt, President & Founder, Good Steward Management, (Website)
Testimonial 3: “Playbook was a tremendous asset as our family navigated the 2025 sale of our family business. With over 6 stockholders the sale necessitated the skills of a business broker that had the ability to work with many parties including our multiple attorneys. Jim and Linda were key to getting a deal done and we appreciate the way they handled the marketing, keeping confidentiality and handling the data room. If you need an experienced firm we recommend you give them a call!”
Margaret A., Shareholder, Confidential Seller
Ready to Sell Your Business? Contact Jim and the Playbook Team Today!
Take the first step towards a successful business sale. Contact us at 312-525-9622 or email us at president@playbookadvisory.com to schedule a free consultation. Let us help you navigate the complexities of selling your business with ease and confidence.
Business Glossary - Commonly Used Terms