Co-Founder & CEO - AI Retail Planning Autopilot

FutureSight • New York, NY

7h

About The Position

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. The market signal is clear: Autopilot is the vision, the pain is in the dollars, not the dashboards, and institutional memory failure is systemic and unresolved. 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! 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.

Requirements

• Previous founding experience at a venture-backed company.
• Demonstrated success in B2B SaaS go-to-market, including sales and customer engagement.
• Fundraising fluency, with the ability to develop investor narratives and close capital.
• Proven ability to attract, develop, and retain top talent.
• Clear-eyed understanding of the risks and demands of co-founding a venture-backed company.
• Deep, operational exposure to merchandise planning, inventory management, and multi-channel retail operations.

Responsibilities

• Set the direction of the venture and lead its execution.
• Refine the ICP, pricing model, and product positioning.
• 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.
• Partner with the FutureSight product and engineering team to ship V1 and iterate on user feedback.
• Lead the seed raise, supported by FutureSight's network and traction.
• Recruit and lead the founding team, and establish the cultural foundation of the company.

Benefits

• Founder equity with meaningful ownership from inception
• Pre-seed capital committed by FutureSight for early hires and MVP development, with potential for follow-on funding
• Studio resources, including embedded design, engineering, growth, and fundraising support from day one
• Investor and advisor network across retail tech and early-stage capital markets
• A true co-creation model in which you operate as CEO with the studio as your partner

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed