Wintrust Ventures

Wintrust Ventures is a division of Wintrust Financial Corporation, established to foster and support the innovative community in Chicago through strategic investments and guidance for venture start-ups. Based in Rosemont, Illinois, Wintrust Financial operates a comprehensive array of financial services, including community banking, wealth management, and specialty finance, across the greater Chicago metropolitan area and southern Wisconsin. Wintrust Ventures collaborates with entrepreneurs across various sectors such as B2B, technology, e-commerce, artificial intelligence, analytics, and software as a service. While maintaining a sector-agnostic approach, it primarily focuses on start-ups that are based or have significant connections in the Chicago area, positioning itself as a key player in the local entrepreneurial ecosystem.

Connor Detjen

Senior Associate

Eric Eversman

Senior Associate

Bailey Moore

Senior Vice President

Past deals in Illinois

Cohesion

Series A in 2021
CohesionIB, Inc. is a technology company based in Chicago, Illinois, that specializes in developing an artificial intelligence-enabled platform for the commercial real estate sector. The company offers an integrated software solution that connects building systems and streamlines operations, enhancing the experiences of tenants and operators. Cohesion's offerings include features like tenant comfort, touchless controls, automated workflows, and actionable insights, all aimed at optimizing portfolio management and increasing property value. Additionally, the platform includes tools such as a digital twin and an agile return suite, providing real estate owners with a comprehensive suite of building solutions that prioritize connectivity and intelligence within their portfolios. Founded in 2018, Cohesion continues to innovate within the realm of smart building technology.

The Mom Project

Series B in 2020
The Mom Project, Inc. is a digital marketplace that connects women with companies seeking to fill various roles across fields such as marketing, finance, technology, and project management. Founded in 2015 and based in Cincinnati, Ohio, the platform serves a community of over 275,000 professionals and more than 2,000 companies, focusing on helping mothers stay active in the workforce. The Mom Project not only provides job opportunities tailored to the needs of working mothers but also offers companies insights into their workplace practices regarding women, along with recommendations to improve conditions for mothers and their employees. By facilitating connections and advocating for better workplace policies, The Mom Project aims to create a more supportive environment for women and redefine career trajectories that align with their personal goals.

Apervita

Venture Round in 2019
Apervita is a trusted healthcare collaboration platform for quality measurement, clinical intelligence, value optimization, and interoperability. They empower payers and providers and other stakeholders to more efficiently and effectively measure clinical and financial performance, improve clinical quality, and administer and run analytics on value-based contracts. By providing an independent, secure, trusted platform to perform shared analyses, Apervita uniquely allows stakeholders to gain mutual, continuous clinical and financial insights and integrate those insights into various systems and workflows simultaneously and at scale. Serving more than one in three hospitals in the United States and several nationally recognized health plans, Apervita conducts more than 10 billion value-based computations and insights for their clients every year. The company maintains office locations in Chicago and Boston.

Packback

Series B in 2019
Packback, Inc. is an educational technology company based in Chicago, Illinois, founded in 2014. It operates an artificial intelligence-driven platform designed to enhance online discussions in academic settings. This platform enables professors to evaluate and improve students' critical thinking skills through structured digital interactions. Packback offers two main products: PB Books, which provides online textbooks on a rental basis, and PB Questions, a digital discussion forum that fosters engagement and personalized learning. The company's innovative approach aims to make learning more engaging and effective, helping students develop a deeper understanding and appreciation for their subjects.

The Mom Project

Series A in 2018
The Mom Project, Inc. is a digital marketplace that connects women with companies seeking to fill various roles across fields such as marketing, finance, technology, and project management. Founded in 2015 and based in Cincinnati, Ohio, the platform serves a community of over 275,000 professionals and more than 2,000 companies, focusing on helping mothers stay active in the workforce. The Mom Project not only provides job opportunities tailored to the needs of working mothers but also offers companies insights into their workplace practices regarding women, along with recommendations to improve conditions for mothers and their employees. By facilitating connections and advocating for better workplace policies, The Mom Project aims to create a more supportive environment for women and redefine career trajectories that align with their personal goals.

Brideside

Seed Round in 2018
Brideside is an apparel and fashion company that offers customized bridesmaid dresses. Brideside provides an online marketplace that allows people to browse bridesmaid dresses and shop online and it specializes in wedding, fashion, and wedding services. The company was founded in 2013 and headquartered in Chicago, Illinois.

The Mom Project

Seed Round in 2018
The Mom Project, Inc. is a digital marketplace that connects women with companies seeking to fill various roles across fields such as marketing, finance, technology, and project management. Founded in 2015 and based in Cincinnati, Ohio, the platform serves a community of over 275,000 professionals and more than 2,000 companies, focusing on helping mothers stay active in the workforce. The Mom Project not only provides job opportunities tailored to the needs of working mothers but also offers companies insights into their workplace practices regarding women, along with recommendations to improve conditions for mothers and their employees. By facilitating connections and advocating for better workplace policies, The Mom Project aims to create a more supportive environment for women and redefine career trajectories that align with their personal goals.

Monica+Andy

Series A in 2018
Monica+Andy is an operator of an online baby clothing shopping platform. The company's baby clothing platform offers an organic clothing line that enables consumers to purchase clothes for their children which are made from trustworthy fabric. Founded in 2014 by first-time mom Monica Royer, Monica + Andy was created from her heart to deliver the softest GOTS-certified organic essentials, to support new parents in a seamless shopping experience online and in Guideshops, and foster a community committed to making things better for babies and making things better for the planet.

Packback

Series A in 2018
Packback, Inc. is an educational technology company based in Chicago, Illinois, founded in 2014. It operates an artificial intelligence-driven platform designed to enhance online discussions in academic settings. This platform enables professors to evaluate and improve students' critical thinking skills through structured digital interactions. Packback offers two main products: PB Books, which provides online textbooks on a rental basis, and PB Questions, a digital discussion forum that fosters engagement and personalized learning. The company's innovative approach aims to make learning more engaging and effective, helping students develop a deeper understanding and appreciation for their subjects.

Curiosity

Series A in 2017
Why do people sneeze in sunlight? Why is a black hole called a "singularity"? Why aren't fish electrocuted when lightning hits the water? Curiosity answers the questions you never knew to ask, and digs into the things you've always wondered about. The company spun out of Discovery in 2014 and today reaches an audience of 70 million a month globally through a website, iOS and Android app, weekly podcast, daily email, Chrome extension, and Amazon Alexa skill. With five new stories on a variety of topics every day (plus thousands more to discover), it helps people have fun learning about everything from the scientific and relatable to the awe-inspiring and downright weird. Count on Curiosity to explain even the densest subjects in a way that's entertaining, witty, and easy to understand.

Rewards21

Series A in 2016
Rewards21, Inc. operates a rewards program that allows clients to earn cash back and reward points for dining at their preferred restaurants. Utilizing a card-linked technology platform, registered consumers can earn cash back by using their credit or debit cards at participating establishments. In addition to dining rewards, the program also provides opportunities for earning cash back and points on hotel, airline, and rental car purchases. Users can redeem their rewards by collecting 2,100 points, which equates to $21 credited directly to their card. Founded in 2015, Rewards21 is headquartered in Arlington Heights, Illinois.

DRYV

Series A in 2016
DRYV LLC is an on-demand dry-cleaning and laundry service that operates through a mobile application, allowing users to schedule pickup and delivery of their garments conveniently. Founded in 2013 and based in Chicago, Illinois, the company serves customers in various neighborhoods in Chicago, Detroit, and Los Angeles. DRYV provides a range of services, including dry cleaning, laundry, and alterations, available seven days a week. As of November 2020, DRYV operates as a subsidiary of Rinse, Inc.

Page Vault

Series A in 2016
Page Vault enables legal professionals to easily capture web content for use as evidence in the U.S. courts. It is a cloud-based Software-as-a-Service subscription solution that provides a trusted third party chain of custody for captures with the simplicity of a screenshot. It was incorporated in 2013 and is based in Chicago, Illinois.

UrbanBound

Series B in 2016
UrbanBound, LLC specializes in relocation management software that assists employers and employees in managing and tracking all facets of job-related relocations. The platform facilitates a seamless experience by enabling employees to review and utilize their relocation benefits while providing companies with tools to attract candidates by showcasing their organizational strengths and culture. UrbanBound also offers specific solutions for managing intern relocations, which include financial disbursements and housing arrangements. Additionally, the software provides comprehensive reporting capabilities that enhance transparency regarding relocation expenditures and streamline tax processes. Founded in 2011 and based in Chicago, Illinois, UrbanBound serves a diverse clientele, including Fortune 500 companies and emerging startups, by delivering a tech-driven approach that improves the relocation experience and reduces overall program costs.

Bucketfeet

Convertible Note in 2016
BucketFeet, Inc., doing business as BucketFeet, designs and manufactures shoes for men, women, and children. It also offers tees, hoodies, and socks. The company provides its products online. BucketFeet, Inc. was founded in 2011 and is based in Chicago, Illinois. As of October 23, 2017, BucketFeet, Inc. operates as a subsidiary of SkinnyCorp, LLC.

Rippleshot

Seed Round in 2015
Rippleshot reduces over 25% of fraud losses for banks and merchants by uncovering merchant data breaches and stopping card fraud sooner. Rippleshot’s technology monitors tens of millions of merchants to pinpoint when and where a data breached occurred. Rippleshot stops losses, protects brand reputation, and safeguards the consumer payment experience. Get immediate results visualized through our cloud-based big data analytics platform.

Bucketfeet

Series A in 2015
BucketFeet, Inc., doing business as BucketFeet, designs and manufactures shoes for men, women, and children. It also offers tees, hoodies, and socks. The company provides its products online. BucketFeet, Inc. was founded in 2011 and is based in Chicago, Illinois. As of October 23, 2017, BucketFeet, Inc. operates as a subsidiary of SkinnyCorp, LLC.

Monica+Andy

Venture Round in 2015
Monica+Andy is an operator of an online baby clothing shopping platform. The company's baby clothing platform offers an organic clothing line that enables consumers to purchase clothes for their children which are made from trustworthy fabric. Founded in 2014 by first-time mom Monica Royer, Monica + Andy was created from her heart to deliver the softest GOTS-certified organic essentials, to support new parents in a seamless shopping experience online and in Guideshops, and foster a community committed to making things better for babies and making things better for the planet.

Bucketfeet

Debt Financing in 2015
BucketFeet, Inc., doing business as BucketFeet, designs and manufactures shoes for men, women, and children. It also offers tees, hoodies, and socks. The company provides its products online. BucketFeet, Inc. was founded in 2011 and is based in Chicago, Illinois. As of October 23, 2017, BucketFeet, Inc. operates as a subsidiary of SkinnyCorp, LLC.

Packback

Seed Round in 2015
Packback, Inc. is an educational technology company based in Chicago, Illinois, founded in 2014. It operates an artificial intelligence-driven platform designed to enhance online discussions in academic settings. This platform enables professors to evaluate and improve students' critical thinking skills through structured digital interactions. Packback offers two main products: PB Books, which provides online textbooks on a rental basis, and PB Questions, a digital discussion forum that fosters engagement and personalized learning. The company's innovative approach aims to make learning more engaging and effective, helping students develop a deeper understanding and appreciation for their subjects.

Lumere

Series A in 2014
Lumere (previously Procured Health) is an organization comprised of clinicians, researchers, pharmacists, and strategic thought leaders focused on helping health systems eliminate unwarranted clinical variation and cut unnecessary costs—specifically related to device and drug selection and utilization. It was incorporated in 2012 and is based in Chicago, Illinois.

Gesture

Series A in 2014
Gesture, LLC operates an online mobile fundraising platform tailored for charities, nonprofits, schools, churches, and political organizations. Founded in 2011 and based in Westmont, Illinois, Gesture specializes in mobile bidding, which allows guests to participate in silent auctions via their smartphones, thereby enhancing fundraising efforts. The platform offers a suite of services including guest management, online ticketing, expedited check-in and checkout processes, direct donations, and real-time dashboards that track user engagement and revenue. Gesture's solutions are designed to streamline the organization of various fundraising events, from school auctions to elegant galas, ensuring clients can maximize revenue through efficient management of live and silent auctions. The company's mobile auction software is user-friendly and PCI-compliant, allowing participants to use their personal devices without needing additional equipment. Gesture's team of experts supports clients throughout the event lifecycle, from registration to post-event reporting, helping them achieve their fundraising goals effectively.