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Added 6 mins ago
Retail Experience Lead
Fire & Flower Inc.
Canmore, AB
The Retail Experience Lead maintains store appearance and product presentation to company standards and acts as a knowledge resource for team members. Duties include but are not limited to…
Added 35 mins ago
PE
Structural Site Supervisor
PTW Energy Services
Calgary, AB
- Full-time
Monitors product standards and maintains quality-control programs.
Added 36 mins ago
WB
Lead Product Sales
Whistler Blackcomb
Whistler, BC
- Temporary
Service is foundation of everything we stand for at Vail Resorts and our Product Sales Team Leaders are no exception to creating this experience of a lifetime. Through facilitating the sale…
Added 36 mins ago
A
Interaction/Visual Designer - Advanced [AQ-25680]
Aquent
Montreal, QC
- $50 to $53 CAD / hour
- Contract
Serve as the go-to subject-matter expert for interaction design, guiding the product design team with your deep knowledge.
Added 36 mins ago
* Technologist *
Oerlikon
Fort Saskatchewan, AB
…customer requirements. This role plays a key part in ensuring product quality and maintaining laboratory…
Added 51 mins ago
FT
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Calgary, AB
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Uphold ZWILLING's customer service standards by actively listening to customer preferences and addressing their needs with product information.
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Mississauga, ON
- Full-time
Support new product development; create bill of materials, routings and fixtures for newly released products.
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JACK & JONES
Richmond, BC
- Part-time
Share product knowledge and styling tips to elevate the experience.
Added 1 hour ago
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Outside Sales Internship / Co-op - 2027
Uline
Hamilton, ON · Milton, ON · Mississauga, ON · Toronto, ON
- Full-time
Take part in two weeks of professional sales training to sharpen your presentation skills and product knowledge.
Added 1 hour ago
CI
Seasonal Associate
Carters Inc.
Windsor, ON
- Part-time
Welcome customers with a warm greeting and provide assistance with our product styles, features, and benefits
Added 1 hour ago
CI
Seasonal Associate
Carters Inc.
Guelph, ON
- Part-time
Welcome customers with a warm greeting and provide assistance with our product styles, features, and benefits
Added 1 hour ago
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Vaughan, ON
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Welcome customers with a warm greeting and provide assistance with our product styles, features, and benefits
Added 1 hour ago
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Financial Manager - PLM (Product Line Mgmt)
Husky Technologies
Bolton, ON
- Full-time
Title: Financial Manager - PLM (Product Line Mgmt)
Added 1 hour ago
HT
Director, Finance (CSM)
Husky Technologies
Bolton, ON
- Full-time
Analyze business performance by region, product line, customer segment, channel, and service offering.
Added 1 hour ago
MG
Sales Associate (Seasonal)
Mind Games USA
Dartmouth, NS
- Part-time
Develop strong product knowledge of games, puzzles, toys, and collectibles.
Added 1 hour ago
FB
Assistant Bakery Manager
Farm Boy Inc.
Ottawa, ON
- From $21 CAD / hour
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Lead regular team huddles to share goals, recognize achievements, exchange product knowledge, and provide meaningful feedback to build engagement and connection.
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- $61,500 to $104,500 CAD / year
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As a Senior Angular Developer, you will make an impact by designing, developing, and enhancing scalable web applications and data integration solutions that support critical business…
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Full Stack Technical Lead (Angular/Java)
Cognizant
Toronto, ON
- $72,000 to $126,000 CAD / year
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…collaboratively with architects, developers, business stakeholders, product owners, and project managers to deliver scalable, secure, and high-performing…
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Contracts & Privacy Specialist
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- Full-time
…for the scientific community. LabX Media Group’s brands and product solutions deliver trusted, timely and deep information across print and digital products to empower our customers and…
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Samsung Home Electronics Sales and Product Specialist
Acosta
Regina, SK
- Full-time
As a Samsung Sales and Product Specialist, you’ll spark sales in retail stores, promote products and excite customers about everything Samsung TV. Growing sales for Premium clients is the…
Added 2 hours ago
U
Outside Sales Internship / Co-op - 2027
Uline
Carleton Place, ON · Cornwall, ON · Embrun, ON · Hawkesbury, ON · Ottawa, ON
- Full-time
Take part in two weeks of professional sales training to sharpen your presentation skills and product knowledge.
Added 2 hours ago
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Implement planogram changes to optimize product placement.

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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