Co-Founder & CEO - AI Retail Planning Autopilot
About the role
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 dedicated planning team. The platform connects across channels and ERPs, handles routine decisions silently, and surfaces exceptions with context and recommended actions before they become revenue losses. Institutional memory is externalized, structured, and queried in plain language.
About FutureSight
FutureSight is a leading venture builder that co‑creates world‑class software companies with values‑driven entrepreneurs from inception to exit. The studio team includes:
- John Carbrey – 4x entrepreneur, $100 M ARR
- Krista LaRiviere – 3x exited, EY Top Women Entrepreneur
- Alan Smith – Strategyzer co‑founder, $120 M in products built
- Prathna Ramesh – former MD of Maple Leaf Angels, $275 M in follow‑on capital
- Johnny Tong – 0‑to‑1 builder, acquired by SAP and Stripe
The partnership provides:
- 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 where the CEO works alongside FutureSight’s cross‑functional team
Responsibilities
- Set the venture’s direction and lead execution
- Strategy: refine the ideal customer profile, pricing model, and product positioning
- Customer Development: lead pilots with VPs, operations managers, and merchandise planners at importers, distributors, and multi‑channel retail brands; convert pilots to paid engagements; build the go‑to‑market motion
- Product: partner with FutureSight’s product and engineering team to ship V1 and iterate based on user feedback
- Capital: lead the seed raise, supported by FutureSight’s network and traction
- Team: recruit and lead the founding team and establish the cultural foundation of the company
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
FutureSight is committed to diversity, equity, and inclusion and welcomes applicants of all backgrounds and experiences.