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FutureSight

Co-Founder & CEO - AI Retail Planning Autopilot

LocationChicago, Illinois, United States
DepartmentEntrepreneur in Residence for FutureSight Ideas
Company size51+ people
First seen1w ago
Last seen2d ago
The Opportunity
FutureSight is seeking a Co-Founder & CEO to lead Maestro, an AI-native inventory-planning intelligence venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role.
Maestro is an autopilot planning intelligence for SMB operators managing physical inventory complexity without a planning team. It connects across channels and ERPs, handles routine decisions silently, and surfaces exceptions with context and a recommended action before they become revenue losses. The institutional memory that today lives only in a planner’s head gets externalized, structured, and queried in plain language.
We didn’t just build a thesis; we validated it directly with the market. We have spoken with founders, VP E-Commerce leaders, merchandise planners, and multi-channel operators at DTC and specialty retail brands across the US. The market signal is clear:
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Autopilot is the vision: Every named competitor generates recommendations that humans still have to act on manually. No product at this revenue tier is building toward full autonomous execution of the planning lifecycle. Maestro’s product vision is full autopilot: the system owns the buy decision, allocation, and markdown trigger end-to-end. But buyers earn that trust incrementally, starting with routine decisions handled silently and exceptions surfaced with context.
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The pain is in the dollars, not the dashboards: Documented annual losses across just five buyer accounts total $1.25–1.5M+. Buyers currently spend $0–500/month on software; the entire planning budget is tied up in headcount. The payback case is immediate, and ROI demonstration, not feature demos, will be the critical sales motion.
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Institutional memory failure is systemic and unresolved: One SVP with 30 years of domain expertise described relying entirely on personal recall to flag which materials, colours, and styles underperformed last season. When he leaves, that knowledge disappears, and no tool captures it today. Every buyer interviewed described a version of this problem.
Market Context
We are targeting a large, structurally underserved segment: SMB operators managing multi-channel physical inventory complexity at $5M–50M revenue — importers, distributors, Amazon aggregators, and specialty retailers. The beachhead SAM is estimated at $200M–$225M across approximately 15K–16K brands in the US and Canada. Excel is the universal incumbent! 5/5 buyers in our discovery sprint were on spreadsheets, with zero dedicated planning tools in use. EBITDA across the $10–50M DTC cohort is compressed to 7.25% in 2025 with revenue declining ~4.6% YoY. Planning waste attacks the margin stack directly.
About FutureSight
FutureSight is a leading venture builder that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale.
You’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 Partnership
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Founder equity with meaningful ownership from inception
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Pre-seed capital committed by FutureSight for early hires and MVP development, with potential for follow-on funding
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Venture building resources, including embedded design, engineering, growth, and fundraising support from day one
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Investor and advisor network across vertical AI and early-stage capital markets
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A true co-creation model in which you operate as CEO with FutureSight’s cross-functional team as your partner
What You’ll Own
As Co-Founder & CEO, you will set the venture’s direction and lead its execution.
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Strategy — Refine the ICP, pricing model, and product positioning
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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
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Product — Partner with the FutureSight product and engineering team to ship V1 and iterate on user feedback
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Capital — Lead the seed raise, supported by FutureSight’s network and traction
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Team — Recruit and lead the founding team, and establish the cultural foundation of the company
Co-Founder Profile
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Previous founding experience at a venture-backed company
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Demonstrated success in B2B SaaS go-to-market, including sales and customer engagement
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Fundraising fluency, with the ability to develop investor narratives and close capital
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Proven ability to attract, develop, and retain top talent
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Clear-eyed understanding of the risks and demands of co-founding a venture-backed company
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Deep, operational exposure to merchandise planning, inventory management, and multi-channel retail operations
How to Apply
Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.
Legal
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.
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