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 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:

Autopilot is the vision: Every named competitor generates recommendations that humans still have to act on manually. 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. But buyers earn that trust incrementally, starting with routine decisions handled silently and exceptions surfaced with context.

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, not feature demos, will be the critical sales motion.

Institutional memory failure is systemic and unresolved: One SVP with 30 years of domain expertise described relying entirely on personal recall to flag which materials, colours, and styles underperformed last season. When he leaves,



that knowledge disappears, and no tool captures it today. Every buyer interviewed described a version of this problem.

The Partnership

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

What You’ll Own

Strategy — Refine the ICP, 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 them to paid engagements, and build the go‑to‑market motion

Product — Partner with the FutureSight product and engineering team to ship V1 and iterate 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

Co-Founder Profile

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

Transparent‑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. We welcome applicants of all backgrounds and experiences.

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📌 Co-Founder & CEO - AI Retail Planning Autopilot (Manitoba)
🏢 FutureSight
📍 Manitoba