[Hiring] Co-Founder & CEO - AI Retail Planning Autopilot @FutureSight

Role Description

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 validated our thesis 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: Autopilot is the vision.
• 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.
• 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 will be the critical sales motion.
• Institutional memory failure is systemic and unresolved.

Qualifications

• 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.

Requirements

• Set the venture's direction 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 pilots 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.
• Venture building resources, including embedded design, engineering, growth, and fundraising support from day one.
• Investor and advisor network across vertical AI and early-stage capital markets.
• A true co-creation model in which you operate as CEO with FutureSight's cross-functional team as your partner.

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.

FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.