Wintrust Financial

Wintrust Financial Corporation is a financial services holding company headquartered in Rosemont, Illinois, with assets exceeding $18 billion. The company operates primarily in the Chicago metropolitan area, southern Wisconsin, and northwest Indiana through its network of community-oriented banking subsidiaries. Wintrust offers a range of services, including personal and commercial banking, mortgage origination, and wealth management. Its Community Banking segment provides deposit accounts, various types of loans, and cash management services to individuals and businesses. The Specialty Finance segment focuses on commercial insurance premium financing and short-term accounts receivable financing, while also offering administrative services such as payroll processing and treasury management. Established in 1991, Wintrust is committed to delivering comprehensive financial solutions tailored to meet the needs of its diverse clientele.

Timothy S Crane

CEO

9 past transactions

Macatawa Bank

Acquisition in 2024
Macatawa Bank Corporation is a bank holding company based in Holland, Michigan, that operates Macatawa Bank. Established in 1997, the bank offers a range of commercial and consumer banking services, including various deposit accounts such as checking, savings, and certificates of deposit. Its lending portfolio encompasses commercial and industrial loans, commercial real estate loans, residential mortgages, and consumer loans like automobile and home equity lines of credit. Additionally, Macatawa Bank provides financial planning, asset management, and trust services, alongside internet and mobile banking options. The bank caters to a diverse clientele, including individuals, businesses, nonprofit organizations, and government entities. As of early 2020, Macatawa Bank operated 26 full-service branches across Kent, Ottawa, and northern Allegan counties in Michigan.

P1 Dental Partners

Debt Financing in 2023
P1 Dental Partners is a Dental Partnership Organization that comprises a network of successful and established dental practices primarily located in the Midwest. The organization collaborates with engaged dental professionals to foster a supportive environment for its affiliated offices. By emphasizing the delivery of clean, safe, and compassionate dental care, P1 Dental Partners aims to inspire high standards of practice among its partners. The company's focus on collaboration and quality care positions it as a key player in the dental industry, committed to enhancing patient experiences and outcomes across its affiliated practices.

CAC Specialty

Debt Financing in 2023
CAC Specialty is an integrated insurance brokerage and investment banking firm that specializes in providing expert services across a wide range of insurance and alternative capital markets. The company offers a diverse array of solutions, including cyber liability, executive liability, environmental risk management, property and casualty insurance, and transactional liability. By leveraging its deep industry knowledge and placement capabilities, CAC Specialty assists businesses and clients in navigating complex risk challenges and enhancing value during mergers and acquisitions. Through its comprehensive approach, the firm aims to deliver tailored solutions that meet the specific needs of its clients in an evolving risk landscape.

SageSure

Debt Financing in 2023
SageSure is a managing general underwriter focused on coastal residential and commercial property markets. Founded in 2009, SageSure specializes in providing over 50 competitively priced insurance products across 14 coastal states through its carrier partners. The company serves more than 415,000 policyholders with over $850 million in-force premium to date. SageSure is known for its innovative online quoting and binding platform, as well as advanced risk modeling and scoring technology. It distributes its products through a network of over 11,400 insurance producers and national brokers, ensuring customers receive expert advice on protecting their assets.

Apervita

Venture Round in 2019
With wasteful healthcare spending in the U.S. estimated at $935 billion, we take our role as a healthcare innovator very seriously. Simply put, we’re on a mission to transform quality measurement and care delivery. To drive toward a Learning Health System—a framework that drives better outcomes and cost efficiencies across the health ecosystem—the industry has to commit to real change. Apervita is that change. Through our solutions and trusted collaboration platform, we’re committed to making the Learning Health System a reality, making healthcare smarter and ultimately improving patient care. As we move into our next phase of growth, we’re looking for passionate and fearless professionals to help us pursue our mission. We’ve earned the trust of our investors, including Optum Ventures, Baird Capital, Pritzker Group Venture Capital and Math Venture Partners, to further grow and scale our business. We’ve also been recognized as an industry leader by Gartner, CIOReview, Healthcare Tech Outlook, and Healthcare Informatics. Always in search of the next “first,” Apervita was named the first company to certify electronic clinical quality measures from the National Committee for Quality Assurance (NCQA) using our proprietary clinical quality language (CQL) ingestion engine. And, we were recently awarded by Healthcare Innovation for our innovative work with The Joint Commission, one of the nation’s largest regulatory organizations. We believe we’re making a difference every day to drive improvements in quality care that lead to better patient outcomes with a lower cost of care. We’re honored to be on this incredibly important journey to build a better healthcare system.

The Mom Project

Seed Round in 2018
The Mom Project, Inc. is a digital marketplace that connects women, particularly mothers, with employment opportunities across various sectors, including marketing, finance, technology, and project management. Founded in 2015 and based in Cincinnati, Ohio, the company serves a community of over 500,000 individuals, including moms, dads, and allies, facilitating access to flexible work arrangements at both large corporations and small businesses. In addition to matching job seekers with employers, The Mom Project also provides insights and recommendations to companies on improving workplace conditions for women, aiming to foster a more supportive environment for mothers while redefining traditional career structures.

First Community Financial

Acquisition in 2016
First Community Financial is the parent company of first community bank that provides various banking and financial services.

Bucketfeet

Debt Financing in 2015
Bucketfeet is a direct-to-consumer shoe brand based in Chicago, Illinois, founded in 2011 by Raaja Nemani and Aaron Firestein. The company collaborates with a global community of artists to design limited-edition shoes, allowing each artist to create unique shoe designs that are printed on sneakers once ordered online. This responsive commerce model enables Bucketfeet to disrupt traditional manufacturing cycles by letting the community select styles they’d like to purchase and wear, thereby informing demand. In addition to shoes, Bucketfeet offers tees, hoodies, and socks, all available for purchase through its online platform. The company aims to spark meaningful conversations and create a brighter world by empowering artists to share their stories and perspectives using art on footwear as their canvas.

Great Lakes Advisors

Acquisition in 2011
Great Lakes Advisors, established in 1990 and headquartered in Chicago, is an employee-owned investment management firm. It offers a range of services, including equity and fixed income investment strategies, primarily for institutional clients such as public funds, endowments, and corporations. The firm manages approximately $2.4 billion in assets, focusing on value-oriented, bottom-up stock picking, and socially responsible investments within the U.S. public equity and fixed income markets.
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