Co-Founder & CEO - AI Wealthtech FutureSightCo-Founder & CEO - AI WealthtechChicago, ILYou’ll co-create with a proven venture building 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. Every wealth management firm already staffs an Operations function to do this work, typically at a ratio of roughly one Operations person to every three advisors, and that function is chronically stretched: slow, error-prone, and unable to give any single advisor's book the full attention it deserves.
Co-Founder & CEO - Entrepreneur In Residence FutureSightCo-Founder & CEO - Entrepreneur In ResidenceChicago, 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. 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-Native Mortgage Origination FutureSightCo-Founder & CEO - Ai-Native Mortgage OriginationChicago, ILYou’ll co-create with a proven venture building 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. Customer discovery validates a real, recurring cost problem in this segment: lenders spend thousands of dollars to originate a single loan today, a cost that's climbed roughly 35% over the past three years, with up to 80% of that time spent on manual document review.
Co-Founder & CEO - AI Retail Planning Autopilot FutureSightCo-Founder & CEO - AI Retail Planning AutopilotChicago, IL$1.25–$1.50 / hourYou’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. Customer Development — Lead pilots with VPs, operations managers, and merchandise planners at importers, distributors, and multi-channel retail brands, convert them to paid engagements, and build the go-to-market motion.
Co-Founder & CEO - AI Native Recruiting Firm FutureSightCo-Founder & CEO - AI Native Recruiting FirmChicago, 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. Foundry is an AI-native recruiting firm built around a simple idea: use AI agents to handle sourcing, screening, and candidate evaluation, and keep a small human team focused on what still requires a person: building trust with clients and candidates, exercising judgment on close calls, and closing the placement.
Co-Founder & CEO - AI Accounting Agents For CPA Firms FutureSightCo-Founder & CEO - AI Accounting Agents For CPA FirmsChicago, 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. 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, 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. 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.
NewProduct CEO / Venture Studio Director - Chicago Human AgencyProduct CEO / Venture Studio Director - ChicagoChicago, ILRemoteOur mission is to bring on individuals, from creative producers to technical experts to entrepreneurial leaders, who can help us realize this next chapter of growth. We're hiring someone who is mostly going to be building and running their own venture within Human Agency's studio — and who also sets the rules for how ventures flow across the entire studio.
Commercial Specialist, Board And CEO Team Egon ZehnderCommercial Specialist, Board And CEO TeamChicago, IL$85,000–$95,000 / yearIn this dynamic role, you will collaborate with our teams of consultants and subject matter experts to drive business development efforts and support the growth of Top of The House (ToTH) relationships across segments – Board Search, Board Effective Reviews, Board Advisory, Spin-out Board projects as well as a range of CEO Succession / CEO Search projects. Lead and support business development initiatives by proactively tracking market trends, company developments, and executive movements to inform strategic outreach in collaboration with the Community Leaders, Research Leader and ToTH Practice Specialists.
Commercial Specialist, Board and CEO Team Egon Zehnder International AGCommercial Specialist, Board and CEO TeamChicago, IL$85,000–$95,000 / yearIn this dynamic role, you will collaborate with our teams of consultants and subject matter experts to drive business development efforts and support the growth of Top of The House (ToTH) relationships across segments - Board Search, Board Effective Reviews, Board Advisory, Spin-out Board projects as well as a range of CEO Succession / CEO Search projects. Lead and support business development initiatives by proactively tracking market trends, company developments, and executive movements to inform strategic outreach in collaboration with the Community Leaders, Research Leader and ToTH Practice Specialists.
Remote CEO for ATAX Franchise ATAX Corporate OfficeRemote CEO for ATAX FranchiseChicago, ILRemoteThe ideal candidate is energized by helping franchise owners succeed while identifying new opportunities to grow the brand and enter new markets. ATAX is looking for a growth-minded CEO to lead and scale a nationally recognized franchise organization serving communities across the United States.
Co-Founder & CEO - AI Native Recruiting Firm FutureSight VenturesCo-Founder & CEO - AI Native Recruiting FirmChicago, IllinoisYou’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. Foundry is an AI-native recruiting firm built around a simple idea: use AI agents to handle sourcing, screening, and candidate evaluation, and keep a small human team focused on what still requires a person: building trust with clients and candidates, exercising judgment on close calls, and closing the placement.
Co-Founder & CEO - AI Healthcare Revenue Recovery FutureSight VenturesCo-Founder & CEO - AI Healthcare Revenue RecoveryChicago, IllinoisYou’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 - Entrepreneur in Residence FutureSight VenturesCo-Founder & CEO - Entrepreneur in ResidenceChicago, IllinoisYou’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 LegalTech | AI-Native Litigation Defence Operations FutureSight VenturesCo-Founder & CEO - AI LegalTech | AI-Native Litigation Defence OperationsChicago, IllinoisYou’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.
Co-Founder & CEO - AI Communication Agents for Freight & Logistics FutureSight VenturesCo-Founder & CEO - AI Communication Agents for Freight & LogisticsChicago, IllinoisYou’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 Retail Planning Autopilot FutureSight VenturesCo-Founder & CEO - AI Retail Planning AutopilotChicago, Illinois$1.25–$1.50 / hourYou’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. Customer Development — Lead pilots with VPs, operations managers, and merchandise planners at importers, distributors, and multi-channel retail brands, convert them to paid engagements, and build the go-to-market motion.
Co-Founder & CEO - AI Accounting Agents for CPA Firms FutureSight VenturesCo-Founder & CEO - AI Accounting Agents for CPA FirmsChicago, IllinoisYou’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 Content Intelligence for Professional Services FutureSight VenturesCo-Founder & CEO - AI Content Intelligence for Professional ServicesChicago, IllinoisYou’ll co-create with a proven venture building 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 platform captures private input through conversation, audio, and dictation, drafts voice-matched content grounded in that person's real expertise, and routes every draft through configurable firm guardrails and human verification before it reaches a ready-to-publish queue.
Co-Founder & CEO - AI E-commerce Operations System FutureSight VenturesCo-Founder & CEO - AI E-commerce Operations SystemChicago, IllinoisYou’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.