Chicago Ventures
Venture capitalChicago · Pre-Seed–Late Stage · 10 people tracked
Also known as Chicago Ventures Founders · CHICAGO VENTURES FUND MANAGEMENT, LLC
Investment thesis
Chicago Ventures positions itself as an early-stage partner to founders building in sectors often overlooked by other investors. The firm writes high-conviction checks, takes board seats, and acts as an active advocate for founders while maintaining direct, candid communication. Its stated areas of interest span supply chain, logistics and warehousing, healthcare, fintech, enterprise tools, consumer media and entertainment, data management, proptech, small business tools, and mobility.
Source: firm website, verified Aug 7, 2026.
Team · 10 people
from the firm's website & public directories
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What they invest in
from 24 of 115 portfolio companiesSaaS ×8AI & Machine Learning ×5Healthtech ×5Enterprise Software ×4Fintech ×4Consumer ×3Digital Health ×3Future of Work ×3
HQs:United States×38Mexico×1
Investments · 115 tracked
founders shown can be your intro pathHouston, US
Jackie DiMonte(Director)Denman Moody Heard(Executive Officer, Director)Jarrod Pollock(Director)Alexander Brown(Executive Officer, Director)Adrian Fortino(Director)
Board seatStuart Larkins· per SEC Form D · $10.1M raise · filed Dec 2025
Scottsdale, US
Stuart Larkins(Director)Jon Kaiden(Director)Larry Jenkins(Executive Officer)Jeffrey M. Pruitt(Executive Officer, Director)
Board seatStuart Larkins· per SEC Form D · $1.3M raise · filed Sep 2015
Chicago, US
Board seatJai Shekhawat· per SEC Form D · $50M raise · filed Feb 2019
Chicago, US
Board seatStuart Larkins· per SEC Form D · $6.7M raise · filed May 2024
HealthJoy is a benefits management platform that consolidates employers' health and wellness offerings into a single digital system guided by AI and human support.
AI & Machine LearningHealthtechHR TechChicago, US
Clint Jones(Director)Brandon Cruz(Director)Stuart Larkins(Director)Shane Cruz(Director)Justin Holland(Executive Officer, Director)Doug Morse-Schindler(Executive Officer)
Board seatStuart Larkins· per SEC Form D
Chicago, US
Robert Ghoorah(Director)Philippe Lunardelli(Executive Officer)Orazio Buzza(Director)Jai Shekhawat(Director)Vipon Sandhir(Executive Officer, Director)Christopher Capps(Director)
Board seatJai Shekhawat· per SEC Form D · $7.5M raise · filed Jan 2018
Skokie, US
Michael Murray(Executive Officer)Thomas Parkinson(Executive Officer, Director, Promoter)Andrew Parkinson(Executive Officer, Director, Promoter)
Board seatStuart Larkins· per SEC Form D
Santa Monica, US
Alex Bamberger(Director)Stefan Heinrich(Executive Officer, Director)Rob Chesney(Director)
Board seatRob Chesney· per SEC Form D
Chicago-based office management platform offering cleaning services and procurement solutions.
Chicago, US
Kathryn Madden(Executive Officer, Director, Promoter)Gleb Zarkh(Director)Paul Lee(Director, Promoter)Orazio Buzza(Director)
Board seatJai Shekhawat· per SEC Form D · $4M raise · filed Mar 2016
Prisidio is a digital vault service that helps individuals and families collect, protect, and securely share important documents, assets, and information.
ConsumerCybersecuritySaaSNaples, US
Rob Chesney(Director)Glenn Shimkus(Co-Founder & CEO)inVanessa Pegueros(Director)James Dugan(Director)Jason Heltzer(Director)Paul Koziarz(Director)
Board seatRob Chesney· per SEC Form D
Kentfield, US
Maya Mikhailov(COO & President)Alejandro Muller(CEO)
Board seatStuart Larkins· per SEC Form D
ZenBusiness (operating as Ureeka) provides AI-powered guidance and support for entrepreneurs to create LLCs and develop business ideas.
Future of WorkLegalTechSaaSHillsborough, US
David Jakubowski(Executive Officer, Director)Stuart Larkins(Director)Melissa Bradley(Director)Robert Gatto(Executive Officer)
Board seatStuart Larkins· per SEC Form D
Betterfly offers employee benefits platform with configurable benefit packages, including life insurance starting from $20,000 MXN and dental insurance from $10,000 MXN, serving Mexican employers and their workforces.
HR TechInsurTechMexico City, MX
Eduardo della Maggiora(Executive Officer, Director)Martin Molina(Director)Cristobal della Maggiora(Executive Officer, Director)
BoardMike Packer(Director)
This page describes PagerDuty Workflow Automation, a product that automates manual business processes for development and IT operations by combining human-in-the-loop steps such as approvals and decisions with technical automation.
Developer ToolsEnterprise SoftwareSaaSChicago, US
Peter Barris(Director)Sean Chou(Executive Officer, Director)Ravi Singh(Executive Officer, Director)
Chowly is a restaurant technology platform that integrates third-party delivery apps with point-of-sale systems and offers bi-directional menu sync, dynamic pricing, dispute management, and AI marketing.
FoodTechSaaSChicago, US
Sterling Douglass-Barnes(Executive Officer, Director)Sterling Douglass(Co-Founder & CEO)Justin McNally(Co-Founder & Chief Innovation Officer)Joseph Lawton(Chief Operating Officer)Tom Lawton(Chief Revenue Officer)Mark Whittle(Chief Technology Officer)
AI-driven data compliance and risk management solutions helping brands, agencies, and publishers manage data integrity across the digital media supply chain.
AI-powered care coordination platform connecting hospitals, health plans, and in-home providers with real-time collaboration and home-based insights.
Highland Park, US
Adam Koopersmith(Director)Tim Handorf(Executive Officer, Director)Tim Kopp(Director)Godard Abel(Director)
Online compliance software giving global teams a single place to manage policies, training, third parties, and investigations.
GoodShip provides a platform for freight transportation procurement and management, unifying systems for RFPs, carrier bidding, and network operations.
AI & Machine LearningEnterprise SoftwareLogistics & Supply ChainSaaSSeattle, US
Ryan Soskin(Co-Founder and CEO)inDavid Tsai(Co-Founder and CTO)inJody Ann Hall(Executive Officer, Director, Promoter)Ty Findley(Director)
Platform and expert team making construction permitting fast, predictable, and transparent.
Philadelphia, US
Theodore Lambert Baumgardner(Executive Officer, Director)Rob Chesney(Director)Kelly Burke(Director)
PartnerRob Chesney· quoted
Madison, US
Eric Langshur(Director)Ted Meisel(Director)Jonathan Baran(Executive Officer, Director)Rishi Shah(Director)Sanaz Cordes(Executive Officer)Lyle Berkowitz(Executive Officer, Director)
Chicago, US
Charlie Connor(Executive Officer, Director)David Barnes(Executive Officer, Director)Andrew Abbott(Executive Officer, Director)
Account activation infrastructure for business banking that automates the switching workflow to make new accounts active primary relationships.
Dover, US
ERIC DUBOE(Director)JACK MCCARTHY(Executive Officer, Director)FERGUS PLANT(Director)STEFANO BENIGNI(Director)HUGO VILLALOBOS(Executive Officer)
PartnerEric Duboe· quoted
E-commerce
Rows marked “SEC filing” are inferred from directors named on the company's SEC Form D — public regulatory data, not a portfolio list published by the firm.
Frequently asked questions
- What stage does Chicago Ventures invest at?
- Chicago Ventures invests at the Pre-Seed, Seed, Series A, Series B, Series C, Late Stage stages.
- What is Chicago Ventures's typical check size?
- Chicago Ventures typically writes checks of $250K – $1M.
- What sectors does Chicago Ventures focus on?
- Chicago Ventures focuses on Consumer, Data & Infrastructure, Enterprise Software, Fintech, Healthtech, Logistics & Supply Chain, Media & Entertainment, Mobility & Transportation, PropTech, SaaS.
- Where is Chicago Ventures located?
- Chicago Ventures is headquartered in Chicago, US.
- Does Chicago Ventures lead rounds?
- Yes, Chicago Ventures leads investment rounds.
Images
Co-investors · 59
Hyde Park Venture Partners (HPVP) is an early-stage venture fund investing in AI, software, and tech-enabled services companies connected to the Midwest, Toronto, or the Southeast.
Techstars is a startup accelerator and early-stage investor that funds ambitious founders and provides capital, mentorship, and access to a global network of investors, operators, and corporate partners.
Sandalphon Capital is an early-stage venture firm that partners with entrepreneurs to help maximize positive outcomes, with a focus on the Midwest and underserved US markets. It also hosts midwest.tech/connect, a virtual summit connecting Midwest startups with investors.
Bullpen Capital is an early-stage venture firm that has funded over 100 companies, focusing on businesses that have found product-market fit but are overlooked by other investors.
US Venture Partners (USVP) is an early-stage venture capital firm investing in information technology and healthcare companies, with four decades of investing experience.
Lightbank is a Chicago-based venture capital firm that invests in early-stage technology companies and provides operational support to portfolio companies. The firm was founded by Eric Lefkofsky and Brad Keywell, entrepreneurs behind Groupon, Mediaocean, InnerWorkings, Echo Global Logistics, and Uptake.
Left Lane Capital is an investment firm focused on hyper-growth consumer and technology businesses that have enduring customer relationships, applying a data-driven, specialized approach to help companies scale.
Origin Ventures is an early-stage venture capital firm backing founders building companies in the artificial intelligence economy, focusing on infrastructure, software, applications, services, and marketplaces that transform productivity and automation.
Jump Capital is a venture capital firm that leads and participates in startup financing rounds, providing capital, strategic guidance, hiring support, and operational assistance to its portfolio companies.
Group 11 is a venture capital firm that backs founders and technology companies, describing its success as entirely dependent on the success of the companies it invests in.
OCA Ventures is a venture capital firm that partners with founders from seed stage onward, providing capital along with strategic advice and introductions across sectors including biotech, healthcare, and technology.
Great Oaks Venture Capital is a New York-based early-stage investor that partners with founders at the earliest stages of company building across the United States.
▶47 more co-investors
Emergence Capital PartnersTribeca Venture PartnersHigh AlphaZeev VenturesGrotech VenturesIronspring VentureFlyover CapitalAndreessen HorowitzGeneral CatalystAlumni VenturesNotable CapitalFJ LabsBain Capital VenturesUberEverywhere VenturesDCVC (Data Collective)Spark CapitalB Capital GroupQuiet CapitalHardware ClubFoundry GroupSocial LeverageHanabi Capital468 CapitalTeamworthy VenturesAnthemis VentureScience VenturesBrand Foundry VenturesSpero VenturesMontage VenturesConversion CapitalSutter Hill VenturesFoundamentalMusha VenturesAutotech VenturesArthur VenturesGeneration Investment ManagementAlpine MeridianTensility Venture PartnersAlpha Venture PartnersFirstMile VenturesLas Olas Venture CapitalUpheaval InvestmentsHealth Velocity CapitalThoma BravoBarrel VenturesRevelry Venture Partners
Firms observed investing alongside Chicago Ventures, from public investor directories. Shared companies are the overlap with Chicago Ventures's recorded portfolio.
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