🌴 JobsLeisure.com

Where Work Meets Adventure

← Back to Leisure Jobs

Co-Founder & CEO - AI Retail Planning Autopilot

Hospitality Full Benefits Career Growth
Company

FutureSight

Location

toronto, Canada

Posted

June 04, 2026

Start Your Adventure

Join our team and work where others vacation

Apply Now

About This Opportunity

The Opportunity

FutureSight is seeking a Co-Founder & CEO to lead Maestro, an AI-native inventory-planning intelligence venture currently in development at our studio. 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:

  • Autopilo...