Co-Founder & CEO - AI Retail Planning Autopilot

FutureSight • Seattle, WA

9d

About The Position

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 designed as an autopilot planning intelligence for SMB operators who manage complex physical inventory without a dedicated planning team. It integrates across channels and ERPs, autonomously handles routine decisions, and flags exceptions with context and recommended actions to prevent revenue loss. The goal is to externalize, structure, and query institutional knowledge in plain language. The market has validated the need for this solution, with clear signals indicating a demand for autonomous execution of the planning lifecycle, moving beyond the recommendation-based systems of competitors. The pain point is financial loss due to planning inefficiencies, with documented annual losses totaling $1.25–1.5M+ across just five buyer accounts. Current software spending is low ($0–500/month), with planning budgets primarily allocated to headcount. The immediate payback case and ROI demonstration are critical for sales. The systemic issue of relying on individual institutional memory for planning is unresolved, as no current tool captures this knowledge effectively. FutureSight, a venture studio with a proven track record in co-creating software companies, is partnering to bring Maestro to market. The studio team comprises experienced founders, operators, and designers.

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.

Responsibilities

• Set the direction of the venture and lead its execution.
• Refine the Ideal Customer Profile (ICP), pricing model, and product positioning.
• Lead customer development, including pilots with VPs, operations managers, and merchandise planners at importers, distributors, and multi-channel retail brands.
• Convert pilot customers to paid engagements and build the go-to-market motion.
• Partner with the FutureSight product and engineering team to ship V1 and iterate based on user feedback.
• Lead the seed raise, supported by FutureSight's network and traction.
• Recruit and lead the founding team.
• Establish the cultural foundation of the company.

Benefits

• Founder equity with meaningful ownership from inception.
• Pre-seed capital committed by FutureSight for early hires and MVP development.
• Potential for follow-on funding.
• Studio resources, including embedded design, engineering, growth, and fundraising support from day one.
• Access to an investor and advisor network across retail tech and early-stage capital markets.
• A true co-creation model in which you operate as CEO with the studio as your partner.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed