Co‑Founder & CEO, AI-Driven Retail Planning Autopilot

Future Sight 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.

• 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 under performed last season. When he leaves, that knowledge disappears, and no tool captures it today. Every buyer interviewed described a version of this problem.

We are targeting a large, structurally underserved segment: SMB operators managing multi‑channel physical inventory complexity at $5M‑50M revenue — importers, distributors, Amazon aggregators, and specialty retailers. The beachhead SAM is estimated at $200M‑$225M across approximately 15K‑16K brands in the US and Canada. Excel is the universal incumbent! 5/5 buyers in our discovery sprint were on spreadsheets, with zero dedicated planning tools in use.

EBITDA across the $10‑50M DTC cohort is compressed to 7.25% in 2025 with revenue declining 4.6% YoY. Planning waste attacks the margin stack directly.

Future Sight is a leading venture builder that co‑creates world‑class software companies with values‑driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale.

You’ll co‑create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co‑founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow‑on capital), and Johnny Tong (0‑to‑1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth.

• Founder equity with meaningful ownership from inception
• Pre‑seed capital committed by Future Sight 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 Future Sight’s cross‑functional team as your partner

• 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 Future Sight product and engineering team to ship V1 and iterate on user feedback
• Capital — Lead the seed raise, supported by Future Sight’s network and traction
• Team — Recruit and lead the…