Co-Founder & CEO - AI Retail Planning Autopilot
Not Disclosed•OtherOn-site
location_onMayor's Walk, Beacon Hill, Boston, Suffolk County, Massachusetts, 02108, United States
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 offering meaningful founder equity, rather than a traditional salaried executive role.
Maestro serves as an autopilot planning intelligence for SMB operators managing physical inventory complexity without a dedicated planning team. The system connects across channels and ERPs, handles routine decisions silently, and surfaces exceptions with context and a recommended action before they become revenue losses. It externalizes the institutional memory that currently lives only in a planner's head, making it structured and queryable in plain language.
We validated this thesis directly with the market, speaking 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: buyers are losing $1.25–1.5M+ annually due to planning inefficiencies, yet they spend $0–500/month on software because their entire budget is tied up in headcount. The vision is full autopilot—where the system owns the buy decision, allocation, and markdown trigger end-to-end—starting with routine decisions handled silently to earn buyer trust incrementally.
Market Context
We are targeting a large, structurally underserved segment: SMB operators managing multi-channel physical inventory complexity at $5M–$50M revenue, including 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 remains the universal incumbent; in our discovery sprint, 5 out of 5 buyers were on spreadsheets with zero dedicated planning tools in use. With EBITDA across the $10–50M DTC cohort compressed to 7.25% in 2025 and revenue declining, planning waste attacks the margin stack directly.
About FutureSight
FutureSight is a leading venture studio 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 will co-create with a proven studio team, including:
- John Carbrey: 4x founder, bootstrapped to $100M ARR
- Joshua Auslander: Seasoned CFO and strategic advisor with $200M aggregate exits
- Alan Smith: Globally recognized early-stage validation expert with 24 products launched and 5M+ books sold
- Prathna Ramesh: Early-stage investor and capital strategy advisor
The Partnership
This role offers a true co-creation model where you operate as CEO with the studio as your partner. Benefits include:
- 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
- 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
How to Apply
Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.
Work location
Work model: On-site
Mayor's Walk, Beacon Hill, Boston, Suffolk County, Massachusetts, 02108, United States
Boston, Massachusetts
Key Responsibilities
- check_circleSet strategic direction for the venture and refine ICP, pricing, and product positioning
- check_circlePartner with product and engineering teams to ship V1 and iterate on user feedback
- check_circleLead customer development pilots and convert prospects into paid engagements
- check_circleLead the seed fundraising process and develop investor narratives
- check_circleRecruit and lead the founding team while establishing company culture
Requirements
- verifiedPrevious founding experience at a venture-backed company
- verifiedDemonstrated success in B2B SaaS go-to-market
- verifiedFundraising fluency
- verifiedDeep operational exposure to merchandise planning, inventory management, and multi-channel retail operations
Benefits & Perks
check_circleMeaningful founder equity with ownership from inceptioncheck_circlePre-seed capital committed for early hires and MVP developmentcheck_circleEmbedded design, engineering, growth, and fundraising support from day onecheck_circleAccess to investor and advisor network across retail tech and early-stage capital markets
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Frequently asked questions about Co-Founder & CEO - AI Retail Planning Autopilot at FutureSight
What does a Co-Founder & CEO - AI Retail Planning Autopilot at FutureSight do?expand_more
Day-to-day, the Co-Founder & CEO - AI Retail Planning Autopilot at FutureSight will set strategic direction for the venture and refine icp, pricing, and product positioning; partner with product and engineering teams to ship v1 and iterate on user feedback; lead customer development pilots and convert prospects into paid engagements; and lead the seed fundraising process and develop investor narratives.
What are the requirements for this Co-Founder & CEO - AI Retail Planning Autopilot role?expand_more
FutureSight is looking for candidates who meet the following requirements: Previous founding experience at a venture-backed company; Demonstrated success in B2B SaaS go-to-market; Fundraising fluency; and Deep operational exposure to merchandise planning, inventory management, and multi-channel retail operations.
Where is the Co-Founder & CEO - AI Retail Planning Autopilot role at FutureSight located?expand_more
Co-Founder & CEO - AI Retail Planning Autopilot at FutureSight is based in Mayor's Walk, Beacon Hill, Boston, Suffolk County, Massachusetts, 02108, United States. This is a on-site role.
Is this Co-Founder & CEO - AI Retail Planning Autopilot job remote, hybrid, or on-site?expand_more
FutureSight has listed this Co-Founder & CEO - AI Retail Planning Autopilot role as on-site.
How much experience is required for this Co-Founder & CEO - AI Retail Planning Autopilot role?expand_more
Candidates for Co-Founder & CEO - AI Retail Planning Autopilot at FutureSight should have executive.
What skills do you need for the Co-Founder & CEO - AI Retail Planning Autopilot role at FutureSight?expand_more
Key skills for Co-Founder & CEO - AI Retail Planning Autopilot at FutureSight include B2B Saas; Merchandise Planning; Inventory Management; Multi-Channel Retail Operations; Fundraising; and Go-To-Market.
What category does the Co-Founder & CEO - AI Retail Planning Autopilot role belong to?expand_more
Co-Founder & CEO - AI Retail Planning Autopilot at FutureSight is part of the sales job category on Recrutus.
About FutureSight
FutureSight operates within the venture capital and private equity principals sector, maintaining a dual headquarters presence in San Francisco, California, and Toronto. The firm functions as a venture studio dedicated to the creation and funding of vertical B2B AI software companies. By partnering with values-driven entrepreneurs, FutureSight guides these ventures from initial concept through to full market launch.
The organization brings together a multidisciplinary team comprising founders, operators, investors, and designers. This collective brings extensive experience in scaling software products and successfully bringing them to market. The studio model allows the firm to actively shape the development of new technologies rather than simply providing capital. Through this approach, FutureSight supports the growth of innovative AI solutions in specific industry verticals.
Browse more roles: All FutureSight jobs, sales jobs on Recrutus.