Co-Founder & CEO - AI Retail Planning Autopilot

About the role

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 provides autopilot planning intelligence for SMB operators managing physical inventory complexity without a planning team, connecting across channels and ERPs, handling routine decisions silently and surfacing exceptions with context and recommended actions before they become revenue losses. The venture has validated its thesis with founders, VP e‑commerce leaders, merchandise planners, and multi‑channel operators at DTC and specialty retail brands across the US, documenting annual losses of $1.25–1.5M+ across five buyer accounts and identifying a $200M–$225M beachhead SAM among ~15K–16K brands in the US and Canada. FutureSight is a venture builder with a team of experienced founders, operators and designers (John Carbrey, Krista LaRiviere, Alan Smith, Prathna Ramesh, Johnny Tong) that will co‑create the company with you.

Responsibilities

• Refine the ICP, pricing model, and product positioning (Strategy).
• 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 (Customer Development).
• Partner with the FutureSight product and engineering team to ship V1 and iterate on user feedback (Product).
• Lead the seed raise, supported by FutureSight's network and traction (Capital).
• Recruit and lead the founding team, and establish the cultural foundation of the company (Team).

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.

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.
• Access to an 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.