Co-Founder & CEO - AI Retail Planning Autopilot
Job Fit Check
Base Career helps you apply smarter for this job.
Key skills for this role
About the Role
FutureSight is seeking a Co-Founder & CEO to lead Maestro, an AI-native inventory-planning intelligence venture for SMB operators. This is a co-founder partnership with meaningful founder equity, not a salaried role.
Key Skills for This Role
Responsibilities
- Set the venture's direction and lead its execution as Co Founder & CEO
- Refine the ICP, pricing model, and product positioning
- Lead pilots with VPs, operations managers, and merchandise planners, convert them to paid engagements, and build the go to market motion
- Partner with the FutureSight product and engineering team to ship V1 and iterate on user feedback
- Lead the seed raise, supported by FutureSight's network and traction
- Recruit and lead the founding team, and establish the cultural foundation of the company
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
Full Job Posting
The Opportunity
- 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.
Market Context
- We are targeting a large, structurally underserved segment: SMB operators managing multi channel physical inventory complexity at CAD 5M–50M revenue.
- The beachhead SAM is estimated at CAD 200M–CAD 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.
The Partnership
- Founder equity with meaningful ownership from inception
- Pre seed capital committed by FutureSight for early hires and MVP development
- 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, 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
- 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
Apply for this job in 1 click
Skip the repetitive application forms
Install the Base Career Chrome Extension and autofill job applications across major job boards with your profile.
Trusted by over 500,000 job seekers on Base Career
More from this employer
More jobs at FutureSight
Technical Co-founder (CTO) - AI Legal Front Desk
Toronto, CAN
FutureSight seeks a Technical Co-founder (CTO) for BloomLex, an AI staffing platform delivering AI workers for law firms. You will own product and engineering, harden voice AI systems, and build the delivery infrastructu
Co-Founder & CTO - AI PropTech for Municipal Approvals
Toronto, CAN
Landera is building workflow intelligence software for development and infrastructure teams. As Co-Founder & CTO, you will architect and build the initial product, lead technical direction, and partner with the CEO on fu