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Added 10 mins ago
CAREERS
Cameron Stephens
Toronto, ON
Full-time
…managers. The Head of Marketing & Communications will be the firm’s lead storyteller and brand steward, thinking strategically about how the firm is positioned in market and executing…
Added 2 hours ago
Vice President of International Business
Peterson House Ltd
Canada
Full-time
Build systematic, replicable, and sustainably scalable global business development framework focusing on market entry, revenue growth, strategic partnerships, channel expansion, key client…
Added 3 hours ago
Store Manager - Roundhouse Centre
Reitmans (Canada) Ltée/Ltd
Windsor, ON
Full-time
Recruitment & Development: Attract top talent, plan succession, and build a high-performing team through training and performance management.
Added 3 hours ago
Account Manager
The Kersheh Group
Montreal, QC
Full-time
Negotiate pricing, product assortments, and terms with retail partners while maintaining margin targets.
Added 3 hours ago
Store Manager - Roundhouse Centre
RCL - Reitmans Canada Ltd/Ltée
Windsor, ON
Full-time
Recruitment & Development: Attract top talent, plan succession, and build a high-performing team through training and performance management.
Added 8 hours ago
Client service consultant
Emplo Inc.
Gatineau, QC
Full-time
…prioritize our people, to ensure we provide a strong culture and development opportunities which enables our team to thrive and to live our purpose. The best part is that you will work with…
Added 11 hours ago
Assistant Manager - Cornerstone Lloydminster
Old Navy
Lloydminster, AB
Full-time
…customer and product operations, merchandising, and talent development. You are responsible for supporting the execution of the store strategy to achieve performance goals. Through…
Added 15 hours ago
Manager, Commercial Growth & Operations
MNP Executive Search & Professional Recruitment
Kelowna, BC
Full-time
…inventory allocation, marketplace expansion, and wholesale channel development. Working closely with leadership, this role ensures products are purchased effectively, priced competitively,…
Added 19 hours ago
Front End Assistant Manager
Walmart Canada
Montreal, QC
Full-time
Position Summary...To support the Store Manager and manage store operations according to Company guidelines and lead Associates to ensure friendly, helpful service and drive profitable…
Added 19 hours ago
Category Manager
Post Consumer Brands
Toronto, ON
Full-time
…pricing, promotion, distribution, and innovation. They will lead the development of compelling customer-specific growth strategies and selling stories that drive mutually beneficial…
Added 21 hours ago
Senior Manager - Trade Marketing
Reckitt
Mississauga, ON
…skills; Influencing, Consultative Selling, Customer strategy; Channel strategy, Sales strategy development, Perform product planning, financial accumen, commercial accumen, Sales…
Added 21 hours ago
Sales & Artistry Executive - Calgary/Vancouver
Charlotte Tilbury
Vancouver, BC
Manage and lead Sales and Artistry Coordinators through ongoing coaching and development. Responsible for the oversight of their performance in their role demonstrated via their retailer…
Added 21 hours ago
Sales & Artistry Executive - Calgary/Vancouver
Charlotte Tilbury
Calgary, AB
Manage and lead Sales and Artistry Coordinators through ongoing coaching and development. Responsible for the oversight of their performance in their role demonstrated via their retailer…
Added 21 hours ago
Assistant Store Manager (Temporary 7 months) - Prince Street Plaza
Reitmans (Canada) Ltée/Ltd
Sydney, NS
Full-time
Talent Support & Development: Participate in hiring, onboarding, and training team members. Support succession planning and contribute to performance management processes.
Added 21 hours ago
Assistant Store Manager (Temporary 7 months) - Prince Street Plaza
RCL - Reitmans Canada Ltd/Ltée
Sydney Indian Reserve No. 28A, NS · Sydney, NS
Full-time
Talent Support & Development: Participate in hiring, onboarding, and training team members. Support succession planning and contribute to performance management processes.
Added 21 hours ago
Sales & Artistry Executive - Calgary/Vancouver
Charlotte Tilbury Beauty
Vancouver, BC
Full-time
Manage and lead Sales and Artistry Coordinators through ongoing coaching and development. Responsible for the oversight of their performance in their role demonstrated via their retailer…
Added 21 hours ago
Sales & Artistry Executive - Calgary/Vancouver
Charlotte Tilbury Beauty
Calgary, AB
Full-time
Manage and lead Sales and Artistry Coordinators through ongoing coaching and development. Responsible for the oversight of their performance in their role demonstrated via their retailer…
Added 23 hours ago
Senior Manager, Commercial Due Diligence & Growth Strategy
Deloitte
Toronto, ON
Full-time
Lead proposal development, client pursuits, and business development activities while strengthening Deloitte's relationships with private equity sponsors, corporate development teams,…
Added 23 hours ago
Assistant Manager, Product Operations - Park Royal S/C
Gap
BC · West Vancouver, BC
Full-time
…If you want to be part of an iconic American brand, and help lead the way for where we’re headed, we’d love to have you join…
Added 1 day ago
Product Manager, Home Financing
BMO
Toronto, ON · BMOPLACE
Full-time
Analyzes lead quality, conversion funnels, and acquisition performance to identify trends, capacity constraints, root causes, and performance gaps by segment, channel, partner, and program.
Added 1 day ago
Assistant Store Manager
Michaels Stores
Saanich, BC
Full-time
Lead and manage merchandise operations to include omni channel
Added 1 day ago
Product Manager
TD
Toronto, ON
Full-time
Liaise with partners (i.e. Marketing, Phone Channel, Retail) to understand industry and customer trends; analyze challenges and identify areas of opportunity through customer research,…
Added 1 day ago
Assistant Manager - New Westminster
Old Navy
New Westminster, BC
Full-time
…customer and product operations, merchandising, and talent development. You are responsible for supporting the execution of the store strategy to achieve performance goals. Through…
Added 1 day ago
Manager, Account Sales & Planning
Samsung Electronics
Mississauga, ON
Full-time
…relationships and driving sales across Dealer, Corporate, Direct, Retail, and Distributor channels with a focus on non-connected devices. This includes developing and implementing account…
Added 1 day ago
National Account Manager Ecommerce
Stanley Black & Decker, Inc.
Mississauga, ON
Full-time
Lead internal and external alignment on promotional planning, submissions, timing, funding, and execution in partnership with Channel Marketing and Amazon.

FutureSight

Co-Founder & CEO - AI Retail Planning Autopilot

Canada

Job type: Full-time
Posting language: English
Posted: Sep 21, 2026

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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

As Co-Founder & CEO, you will define the venture's strategic direction, refine the product-market fit, and lead customer development efforts. You will also be responsible for recruiting the founding team, managing product iteration, and leading the seed fundraising process.

Requirements

Candidates must have previous founding experience at a venture-backed company and deep operational expertise in merchandise planning and retail operations. Strong proficiency in B2B SaaS go-to-market strategies and the ability to secure capital are essential.

Skills

B2B SaaS
Go-to-market strategy
Fundraising
Merchandise planning
Inventory management
Multi-channel retail
Customer development
Product strategy
Team leadership
Sales
Customer engagement
Operational management
AI product development
Strategic planning

Benefits

Founder equity
Pre-seed capital
Venture building resources
Investor and advisor network

Visa sponsorship

Not detected in the job text

Hiring contact

John Carbrey

Keywords

AI-native
Inventory-planning
B2B SaaS
SMB
ERP
DTC
Merchandise planning
Inventory management
Go-to-market
Seed raise
Venture builder
Product positioning
Operational exposure
Multi-channel retail
Founder equity
MVP development
Vertical AI
E-commerce
Strategy
Customer development

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