Co-Founder & CEO - AI Communication Agents for Freight & Logistics FutureSightCo-Founder & CEO - AI Communication Agents for Freight & LogisticsChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. HawkAI deploys always-on, multi-channel "AI workers" that autonomously manage high-volume freight communications across calls, texts, and emails, integrating directly with core freight systems including TMS, load boards, and broker/carrier databases.
Co-Founder & CEO - AI E-Commerce Operations System FutureSightCo-Founder & CEO - AI E-Commerce Operations SystemChicago, ILYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. Sellers operating across Amazon, Shopify, eBay, Walmart, and other channels constantly switch between dashboards, reconcile conflicting data, and make hundreds of operational decisions every day across pricing, inventory, advertising, fulfillment, and customer support.
Chief Financial Officer YEAR UP CORPORATIONChief Financial OfficerChicago, IL$300,000–$350,000 / yearYear Up United's nationwide presence includes Arizona, Austin, Bay Area, Charlotte, Chicago, Dallas/Fort Worth, Greater Atlanta, Greater Boston, Greater Philadelphia, Jacksonville, Los Angeles, the National Capital Region, New York City/Jersey City, Pittsburgh, Puget Sound, Rhode Island, South Florida, Tampa Bay, and Wilmington. These inequities only further perpetuate the opportunity gap that exists in our country-a gap that Year Up United is determined and positioned to close through three interconnected strategies: providing targeted skills training and connections to livable-wage employment for students and alumni; empowering others to serve and support young adults, and changing systems that perpetuate the opportunity gap.
Entrepreneur in Residence - Technical Co-founder (CTO) FutureSightEntrepreneur in Residence - Technical Co-founder (CTO)Chicago, ILRemoteBuild — Use modern tools and frontier models to move fast without sacrificing quality or maintainability, designing agentic systems with first-principles thinking and knowing when orchestration adds genuine leverage versus when simplicity is the better call. Technical Direction — Own problem framing, architecture, system design, and product judgment from day one, translating rough product intent into structure, context, and specs that both humans and AI systems can execute against.
Co-Founder & CEO - AI Communication Agents For Freight & Logistics FutureSightCo-Founder & CEO - AI Communication Agents For Freight & LogisticsChicago, ILYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. HawkAI deploys always-on, multi-channel "AI workers" that autonomously manage high-volume freight communications across calls, texts, and emails, integrating directly with core freight systems including TMS, load boards, and broker/carrier databases.
Co-Founder & CEO - Entrepreneur in Residence FutureSightCo-Founder & CEO - Entrepreneur in ResidenceChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. Validation — Partner with our team on early-stage testing, validation, and refinement of the business idea, including prototyping to validate and sell potential solutions, with the readiness to kill ideas that don't hold up before committing to the one that does.
Co-Founder & CEO - AI WealthTech FutureSightCo-Founder & CEO - AI WealthTechChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. It integrates market and news signals with client and portfolio data to surface prioritized next-best actions and auto-draft client communications in the advisor's voice.
Co-Founder & CEO - AI Clinical Documentation Compliance FutureSightCo-Founder & CEO - AI Clinical Documentation ComplianceChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. The market signal is incredibly strong: Unprompted Product Pull: Every single lead described the exact product we want to build: a pre-billing, real-time, EHR-integrated flagging layer that checks documentation against payer-specific rules before claims are submitted.
Co-Founder & CEO - AI Healthcare Revenue Recovery FutureSightCo-Founder & CEO - AI Healthcare Revenue RecoveryChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. Reclaim AI resolves denied and aged claims end-to-end, embedding outcome-based contingency pricing—meaning practices pay zero upfront, and we only take a cut of the dollars we successfully recover, for our target ideal customer profile (practices with $80K+ in annual recoverable claims).
Co-Founder & CEO - AI Accounting Agents for CPA Firms FutureSightCo-Founder & CEO - AI Accounting Agents for CPA FirmsChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. Crossfoot is agentic accounting for small-to-mid CPA firms; a segment where accountant shortages are structural, client intake is capped by production headcount, and the manual close and tax prep workflow consumes the majority of senior staff capacity.
Co-Founder & CEO - AI LegalTech | AI-Native Litigation Defence Operations FutureSightCo-Founder & CEO - AI LegalTech | AI-Native Litigation Defence OperationsChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. Product — Partner with the FutureSight product and engineering team to ship V1 (records retrieval, key-fact flagging, billing-reasonableness analysis, and discovery triage) and iterate on user feedback; sequence carrier reserving and prediction as a later phase.
Director National Title Production Advocus National Title Insurance CompanyDirector National Title ProductionChicago, IllinoisJob Profile: Director of National Title Services Job Description Summary: The Director of National Title Operations is responsible for the day-to-day management of title production operations across Advocus National Title Insurance Company’s underwriting business and direct title operations. Monitor workflow, staffing levels, production queues, and file pipelines to ensure timely completion of search package delivery, abstract, title commitment and related title products as needed per individual market demand.
Chief Claims Officer, Argo Group Argo Group International Holdings IncChief Claims Officer, Argo GroupChicago, ILPossesses an extensive knowledge and experience with adjudicating and management claims for a portfolio of commercial products/program lines including surety, auto, general liability, workers' compensation, property, asbestos/environmental, reinsurance and the relevant claims handling practices supporting such products/programs. The Chief Claims Officer, Argo Group provides claim leadership and direction to the Senior Management of all the Argo Group claims operations with a focus on supporting the consistent execution of claims functions and maintenance of operational excellence.
Billing Specialist -Full-Time ELEVATION INDIVIDUAL AND FAMILY THERAPY PLLCBilling Specialist -Full-TimeChicago Heights, ILThe Billing Specialist will utilize their knowledge of revenue cycle management, commercial and Illinois Medicaid billing requirements, and medical billing systems to support the company's medical billing and revenue operations. Skilled at establishing and maintaining positive and effective work relationships with co-workers, clients, members, providers, and other business partners.
Senior Manager, CFO Advisory - Cost Optimization & Value Creation West Monroe Partners, LLCSenior Manager, CFO Advisory - Cost Optimization & Value CreationChicago, IL$194,100–$228,400 / yearThis role is designed for a finance transformation leader who combines financial rigor, operating model expertise, analytical depth, and practical implementation experience to help CFOs and private equity sponsors deliver sustainable cost improvement. Establish defensible cost baselines across labor, third-party spend, technology, facilities, and other operating expenses using general ledger, payroll, procurement, vendor, organizational, and operational data.
Clinical Research Coordinator 2 - Pediatrics University of ChicagoClinical Research Coordinator 2 - PediatricsChicago, IL$60,000–$75,000 / yearThe Pediatric Clinical Trials Office (Peds CTO) is an existing centralized support office that provides services and high-level guidance to individuals (faculty, investigators, research staff, and clinic coordinators from the University and Hospital) involved in human subjects research. The CRC 2 will be involved in multiple research trial types: multi-centered cooperative group and intergroup studies at a national level, multi-institutional pharmaceutical trials, and multi-centered trials designed, implemented and coordinated in a disease-specific Section.
Business Development Executive ConvrBusiness Development ExecutiveChicago, ILRemoteOur modular platform manages underwriting from submission through quote with a purpose-built AI decisioning context engine - grounded in a commercial insurance ontology - ensuring complete data and smarter decisions, faster, while enabling a frictionless experience and superior performance. Role Overview: As a Convr Business Development Executive (BDE) you will use your extensive experience, domain expertise and consultative selling skills to initiate and support sales of the Convr d3 Platform with Large Enterprise prospects.
Wellness Sales Representative (Schaumburg) TVG-Medulla LLCWellness Sales Representative (Schaumburg)Schaumburg, ILAs a Wellness Sales Representative you will: Execute wellness screening events and workshops at business, retail and community venues to educate attendees on spinal health, the positive impacts of chiropractic care and convert these leads to new patient appointments. Medulla is comprised of 830+ employees, with corporate headquarters in Oak Brook, IL and 150+ clinic locations in Illinois, Indiana, Wisconsin, Missouri, Kansas, Kentucky, West Virginia, Texas, Oregon, Washington, and Alaska.
Chief Technology Officer - IntelliScript (Remote) Milliman IncChief Technology Officer - IntelliScript (Remote)Chicago, ILRemote$254,900–$498,295 / year10+ years of experience in leadership roles, including 3+ years of prior experience in a CTO role demonstrating the ability to effectively lead teams and drive strategic initiatives. For candidates residing in: Alaska, California, Connecticut, Illinois, Maryland, Massachusetts, New Jersey, New York City, Pennsylvania, Virginia, Washington, or the District of Columbia the range is $293,135 - $498,295.
Entrepreneur In Residence - Technical Co-Founder (Cto) FutureSightEntrepreneur In Residence - Technical Co-Founder (Cto)Chicago, ILBuild — Use modern tools and frontier models to move fast without sacrificing quality or maintainability, designing agentic systems with first-principles thinking and knowing when orchestration adds genuine leverage versus when simplicity is the better call. Technical Direction — Own problem framing, architecture, system design, and product judgment from day one, translating rough product intent into structure, context, and specs that both humans and AI systems can execute against.