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Added 9 mins ago
HT
Material Handler
Husky Technologies
Bolton, ON
- Full-time
…an ambitious growth strategy that means exceptional career development opportunities and a chance to be a part of a team that is the best in the world at what we do. APPLY TODAY – join the…
Added 9 mins ago
Q
Lead Software Test Framework Engineer
Qualcomm
Markham, ON
- Full-time
We are searching for a Software Test Framework Engineer Lead to be a part of the QCT AI Proc Solution team responsible for design and integration of leading edge technologies in the area of…
Added 24 mins ago
AF
Principal, AI Agent Control & Governance
ATB Financial
Calgary, AB
- Full-time
At ATB, we exist to make it possible for our clients, team members and communities. Our purpose is more than aspirational. It's a real commitment we live every day through our values (what…
Added 24 mins ago
Staff Software Developer, Google Cloud
Google
Waterloo, ON
As part of Cloud's Application Development Platform, the Cloud Source team manages products that organize source code, track its lifecycle into Google Cloud platform (GCP), and generate…
Added 24 mins ago
Field Sales Representative III, Enterprise Growth, Cloud
Google
Montreal, QC
10 years of experience in quota-carrying cloud or software sales, or consultative account management at a business-to-business (B2B) software company.
Added 24 mins ago
Manager, Agent Development, Applied AI
Google
Toronto, ON · Waterloo, ON
Like Google's own ambitions, the work of a Software Developer goes way beyond just Search. Software Development Managers have not only the technical expertise to take on and provide…
Added 39 mins ago
SC
Engineering Manager
SYSTRA Canada
Toronto, ON
- Full-time
Reporting to the Corridor Delivery Lead, the Engineering Manager will lead on engineering deliverables on one, or more, Rail Corridors on the GO Expansion Program, to ensure the best…
Added 1 hour ago
F
Co-Founder & CEO - AI Retail Planning Autopilot
FutureSight
Canada
- Full-time
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…
Added 1 hour ago
F
Technology and Product Co-founder - AI for SEC/FINRA Compliance
FutureSight
Canada
- Internship
A typical 5-person team loses ~3,000 hours a year to triage and status chasing, about $250K in leakage per mid-market firm.
Added 1 hour ago
F
Technology and Product Co-founder - AI for SEC/FINRA Compliance
FutureSight
Canada
- Internship
A typical 5-person team loses ~3,000 hours a year to triage and status chasing, about $250K in leakage per mid-market firm.
Added 1 hour ago
NG
Senior Ventilation Technician
New Gold Inc.
Emo, ON
- Full-time
…intermediate gold mining company engaged in the operation, development and exploration of mineral properties. Our mission is be a leading intermediate gold producer, driving responsible and…
Added 1 hour ago
F
Co-Founder & CEO - AI Retail Planning Autopilot
FutureSight
Canada
- Full-time
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…
Added 1 hour ago
IG
Global Head of Digital Strategy & Transformation
Ingenio Global
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Lead and develop the existing Business Technology and Application Development team.
Added 2 hours ago
M
Senior Data Architect
Miratech
Toronto, ON · Scarborough, ON
- Full-time
…model. You will also partner with the existing CCARS pipeline team through parallel run and decommissioning of the legacy…
Added 2 hours ago
T
Director of Engineering
TAIRC
ON · Regional Municipality of York, ON
- Volunteer
Lead engineering teams: Manage software and hardware engineering teams, ensuring projects are completed on time and within budget.
Added 2 hours ago
IE
Analyst, Business
IMAX Enhanced | Streaming & Consumer Technology
Mississauga, ON
- Full-time
With our global team spanning North America, Europe, and Asia, IMAX brings together proprietary software, world-class architecture, and cutting-edge technology with deep industry expertise.…
Added 3 hours ago
CO
Systems Analyst
City of North Vancouver
North Vancouver, BC
- Full-time
Participate in and occasionally lead Joint Application Development (JAD) sessions
Added 3 hours ago
LL
Transportation Supervisor (Night Shift)
Lineage Logistics
Winnipeg, MB
- Full-time
As a Transportation Supervisor, you will lead a small, dedicated team to ensure the efficient daily operations of pick-ups and deliveries while playing a critical role in representing our…
Added 4 hours ago
FC
ENGINEERING LEAD POST BOOKING OPTIMIZATION - TORONTO, ON
Flight Centre Travel Group Canada
ON · Ontario, Canada
- Full-time
Champion an AI-assisted software development lifecycle, applying AI across design, build, testing, and review to lift both the pace and the quality of what we deliver.
Added 4 hours ago
CI
Process Engineer
CF Industries
Medicine Hat, AB
- Full-time
Lead and/or support the development of projects and MOCs supporting the planning, organization, cost control and implementation of approved projects. These projects will include purchasing…
Added 5 hours ago
MC
Senior Salesforce Administrator
Make-A-Wish Canada
Toronto, ON
- Full-time
We are looking for a Sr Salesforce Administrator to join our team at Make-A-Wish Canada. Reporting to the Manager of Business Applications, you will be responsible for the execution of…
Added 5 hours ago
AA
Expert en ingénierie d'intégration des moteurs / Engine Integration Engineering Expert
Airbus Aircraft
Montreal, QC
- Full-time
Added 5 hours ago
Lead, Geospatial Platform Operations
City of Edmonton
AB
…driving digital innovation and leading high performing teams? The Lead, Geospatial Platform Operations is a senior technical leadership role within the Enterprise Geospatial Technology…
Added 5 hours ago
S
Engineering Manager
SYSTRA
Toronto, ON
- Full-time
Reporting to the Corridor Delivery Lead, the Engineering Manager will lead on engineering deliverables on one, or more, Rail Corridors on the GO Expansion Program, to ensure the best…
Added 5 hours ago
J
Insurance Technology Sales Executive
Jobgether
Canada
- $80,000 to $95,000 CAD / year
- Full-time
As an Insurance Technology Sales Executive, you will drive business growth by introducing innovative software solutions to brokers, insurers, and Managing General Agents (MGAs) across…

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, sales conversion, product delivery, and go-to-market execution. Lead fundraising and recruit and manage the founding team in partnership with FutureSight.

Requirements

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

Skills

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

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

AI
Retail Planning
Inventory Planning
Autonomous Planning
SMB
B2B SaaS
Venture Building
Founder Equity
Pre-Seed Funding
Seed Fundraising
Customer Development
Go-to-Market
Merchandise Planning
Inventory Management
Multi-Channel Retail
DTC
Importers
Distributors
Amazon Aggregators
Specialty Retail
ERP Integration
E-Commerce
Product Strategy
Pricing Model
Pilot Programs
Allocation
Markdown Management
Exception Management
Institutional Memory
Revenue Optimization

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