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Added 2 mins ago
WH
Senior Privacy Analyst - Advisory
WELL Health Technologies Corp. (TSX: WELL)
Toronto, ON
- Full-time
Partner with product, engineering, clinical, and project teams from the start of new digital health initiatives, such as virtual care, patient apps, EMR integrations, and data platforms.
Added 2 mins ago
TH
Health Information Analyst - CHIM
The Hospital for Sick Children
Toronto, ON
- Full-time
…centres in the world. As innovators in child health, we lead and partner to improve the health of children through the integration of healthcare, leading-edge research and education. Our…
Added 3 mins ago
SJ
Growth Manager
So Jobs
Mississauga, ON
- $93,500 to $125,000 CAD / year
- Full-time
Partner with Finance to oversee trade investment budgets, accruals, audits, and reconciliation activities.
Added 33 mins ago
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Co-Founder & CEO - AI Retail Planning Autopilot
FutureSight
Canada
- Full-time
A true co-creation model in which you operate as CEO with FutureSight's cross-functional team as your partner
Added 33 mins ago
KR
Project Accountant
Kassen Recruitment
Burlington, ON
- $80,000 to $100,000 CAD / year
- Full-time
Partner with project and construction teams to support budgeting, forecasting, and financial planning
Added 33 mins ago
F
Co-Founder & CEO - AI Retail Planning Autopilot
FutureSight
Canada
- Full-time
A true co-creation model in which you operate as CEO with FutureSight's cross-functional team as your partner
Added 33 mins ago
TO
Deputy CAO
Town of Peace River
Peace River, AB
- Full-time
Supporting the CAO and Council: Act as a strategic advisor and key partner to the CAO, participate in senior leadership decisions and act on behalf of the CAO, within delegated authority,…
Added 33 mins ago
IG
Global Head of Digital Strategy & Transformation
Ingenio Global
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Added 33 mins ago
NB
Senior Director Communications Transformation
National Bank of Canada
Montreal, QC
- Full-time
…Intelligence, Innovation Management, Learning Agility, Mobilization, Partner Development, Resiliency, Risk Management, Strategic Vision, Strategy Execution, Stress…
Added 33 mins ago
AS
Applied Scientist II, Sponsored Products and Brands Agent
Amazon Science
Toronto, ON
- Full-time
Added 48 mins ago
CN
Director, Marketing Partnerships Lead – NBA Canada
CAN NBA Canada
Toronto, ON
- Full-time
…execution of rights, activations, and benefits, thereby maximizing partner satisfaction and…
Added 1 hour ago
D
Registered Social Worker - MSW (Children and Teens)
DiveThru
St. Albert, AB
- Contract
…services include therapy and psychological assessments. We also partner with organizations to make mental health support more accessible for their…
Added 1 hour ago
D
Registered Social Worker - MSW (Children and Teens)
DiveThru
AB · Edmonton, AB
- Contract
…services include therapy and psychological assessments. We also partner with organizations to make mental health support more accessible for their…
Added 1 hour ago
D
Registered Provisional Psychologist (Children and Teens)
DiveThru
St. Albert, AB
- Contract
…services include therapy and psychological assessments. We also partner with organizations to make mental health support more accessible for their…
Added 1 hour ago
D
Registered Psychologist (Children and Teens)
DiveThru
St. Albert, AB
- Contract
…services include therapy and psychological assessments. We also partner with organizations to make mental health support more accessible for their…
Added 1 hour ago
D
Registered Provisional Psychologist (Children and Teens)
DiveThru
AB · Edmonton, AB
- Contract
…services include therapy and psychological assessments. We also partner with organizations to make mental health support more accessible for their…
Added 1 hour ago
M
Senior Data Architect
Miratech
Toronto, ON · Scarborough, ON
- Full-time
…standards, and the Gold-layer dimensional model. You will also partner with the existing CCARS pipeline team through parallel run and decommissioning of the legacy…
Added 1 hour ago
IE
Analyst, Business
IMAX Enhanced | Streaming & Consumer Technology
Mississauga, ON
- Full-time
…cutting-edge technology with deep industry expertise. Together, we partner with leading filmmakers and studios, advance entertainment technology, and connect audiences around the world to…
Added 1 hour ago
E
Country Manager Canada
elockers
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Be where the action is: Travel regularly across Canada to represent Elockers at events, industry gatherings and strategic partner meetings.
Added 1 hour ago
E
Countrymanager Canada
elockers
Toronto, ON
- Full-time
Be where the action is: Travel regularly across Canada to represent Elockers at events, industry gatherings and strategic partner meetings.
Added 2 hours ago
DG
Traffic Controller
Dawson Group
Shuswap, BC
- Full-time
…collaboratively to coordinate the traffic control plans and is a key partner in ensuring that projects are completed on time and within budget. The ideal candidate will effectively work…
Added 2 hours ago
LC
Associate Faculty - Clinical Nursing
Lambton College
Sarnia, ON
- Part-time
Candidates must be able to work cooperatively with students, faculty, and personnel in clinical partner agencies
Added 2 hours ago
CC
Head of Sales
Citation Canada
Toronto, ON
- Full-time
…Health & Safety content. We are your trusted HR and Safety partner, for all Canadian…
Added 2 hours ago
TA
Alpha Jet Pilot
Top Aces
Canada
- Full-time
…U.S., Germany, and multiple other NATO allies and international partner…
Added 2 hours ago
A
Senior Government Funding Consultant
Ayming
Montreal, QC
- Full-time
Partner with Sales and consulting teams to develop tailored funding strategies aligned with client projects.

FutureSight

Co-Founder & CEO - AI Retail Planning Autopilot

Canada

Full-time

Apply About employer

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Job details

Job type: Full-time
Posting language: English
Posted: Nov 6, 2026

Original job description

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. 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.

Market Context

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.

About FutureSight

FutureSight 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.

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

As Co-Founder & CEO, you will set the venture's direction and lead its execution.

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
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

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.

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More about this job

Responsibilities

Set the venture’s strategy and lead customer development, pilots, paid conversions, and go-to-market execution. Partner with FutureSight to ship and iterate on the product, raise seed capital, and recruit and lead the founding team.

Requirements

Candidates should have prior venture-backed founding experience, a record of B2B SaaS go-to-market success, fundraising fluency, and the ability to attract and retain talent. Deep operational experience in merchandise planning, inventory management, and multi-channel retail is also required.

Skills

Venture Founding
B2B SaaS Go-to-Market
Sales
Customer Development
Fundraising
Investor Relations
Merchandise Planning
Inventory Management
Product Strategy
Pricing Strategy
Market Positioning
Team Building
Talent Development
AI Product Development
Leadership

Benefits

Founder Equity
Pre-Seed Capital
Venture-Building Resources
Design, Engineering, Growth, and Fundraising Support
Investor and Advisor Network

Visa sponsorship

Not detected in the job text

Keywords

Artificial Intelligence
Retail Planning
Inventory Planning
Autonomous Planning
Merchandise Planning
Inventory Management
Multi-Channel Retail
SMB
DTC
ERP Integration
E-Commerce
B2B SaaS
Customer Development
Go-to-Market
Product Positioning
Pricing Model
Pilot Programs
Seed Fundraising
Venture Building
Pre-Seed Capital
Founder Equity
Allocation
Markdown Optimization
Demand Planning
Exception Management
Institutional Memory
Excel
Importers
Distributors
Specialty Retail

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