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, founded in 1997 and headquartered in Holland, Michigan, operates as a bank holding company for Macatawa Bank, which offers a range of commercial and consumer banking services. The bank accepts various types of deposits, including checking and savings accounts, certificates of deposit, and money market accounts. Its lending portfolio encompasses commercial loans for business operations and real estate, residential mortgages, and personal loans such as automobile and home equity loans. Additionally, Macatawa Bank provides financial planning, asset management, cash management, and trust services. The bank also facilitates internet and mobile banking, as well as debit card processing. Serving individuals, businesses, and organizations across Kent, Ottawa, and northern Allegan counties, Macatawa Bank aims to meet the diverse financial needs of its community.

P1 Dental Partners

Debt Financing in 2023
P1 Dental Partners is a Dental Partnership Organization that brings together a network of established and successful dental practices primarily located in the Midwest. The organization focuses on collaborating with dedicated dental professionals to enhance the quality of care provided by its affiliated offices. By fostering a supportive environment, P1 Dental Partners aims to inspire its partner practices to deliver safe and compassionate dental care to their communities.

CAC Specialty

Debt Financing in 2023
CAC Specialty is an insurance brokerage and investment banking firm that specializes in delivering expertise across various areas of insurance and alternative capital markets. The company offers a wide range of services, including cyber liability, executive liability, environmental risk management, and transactional liability, as well as support for mergers and acquisitions and value creation. By providing tailored solutions, CAC Specialty helps businesses and clients effectively manage their risk challenges and navigate complex insurance needs.

SageSure

Debt Financing in 2023
SageSure is a managing general underwriter that specializes in coastal residential and commercial property insurance markets in the United States. Established in 2009, the company offers over 50 competitively priced insurance products across 14 coastal states, serving approximately 415,000 policyholders with more than $850 million in in-force premium. SageSure utilizes a tech-focused approach, featuring an advanced online quoting and binding platform along with sophisticated risk modeling and scoring technology. The company distributes its products through a network of over 11,400 insurance producers and national brokers, ensuring that customers receive tailored solutions that protect their most valuable assets while helping them save on premiums without sacrificing coverage.

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 flexible employment opportunities across various sectors, including marketing, finance, technology, and project management. Established in 2015 and based in Cincinnati, Ohio, the platform serves a community of over 500,000 moms, dads, and allies, facilitating access to job openings at both Fortune 500 companies and small businesses. In addition to matching jobseekers with suitable roles, The Mom Project provides companies with insights into their workplace policies regarding women and offers recommendations to improve conditions for mothers and their employees. By promoting a more supportive work environment, The Mom Project aims to redefine career structures for women and enhance their professional potential while balancing personal goals.

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 that allows artists to create shoe designs and prints them on sneakers once ordered online. Each pair of BucketFeet is designed by a different artist. Find curated inspiration that connects you with the artists that design them. It collaborates with a global community of artists to design limited-edition shoes with the goal of sparking meaningful conversations to create a brighter world. Through a responsive commerce model, Bucketfeet is disrupting traditional manufacturing cycles and redefining the $300B footwear industry, letting the company community select styles they’d like to purchase and wear to help inform demand. It empowers artists to share their stories and perspectives using the universal language of art and the shoe as their canvas. Bucketfeet was founded in 2011 by Raaja Nemani and Aaron Firestein and is headquartered in Chicago, Illinois, USA.
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