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Added 22 mins ago
R
Senior Manager, Initiatives & Implementation Business Financial Services
RBC
Halifax, NS
- Full-time
Supports the Canadian Banking Sales & Field Operations Communication Delivery Gateway Operating Model regionally (E.g.: Aligns, integrates, coordinates and manages prioritization of…
Added 22 mins ago
T
Personal Banking Associate
TD
Brampton, ON
- Full-time
Recommend improvements to work practices, branch operations and processes to enhance customer experience and achieve operational excellence
Added 36 mins ago
TC
Assessment Manager (EU / NA)
Trindent Consulting
Canada
- Full-time
Train, coach, and mentor Operations staff, providing practical guidance on assessment methods, analysis, client communication, and deliverable quality.
Added 36 mins ago
LI
Finance Accounting Manager
Leaf Infusions Inc.
New Westminster, BC
- Full-time
Added 36 mins ago
A
Supervisor, Customer Service & Administration
ATCO
Yellowknife, NT
- Full-time
As Supervisor, Customer Service & Administration, you'll lead the day-to-day delivery of customer service, billing, and administrative operations for Naka Power Utilities (NWT).
Added 1 hour ago
IG
Bilingual Service Rep
Insight Global
Montreal, QC
- $21 CAD / hour
- Full-time
2–3+ years of relevant experience within banking or financial services operations.
Added 1 hour ago
UO
Director, Child Care Services
University of Victoria
Victoria, BC
- Full-time
Excellent administrative and organizational skills to manage diverse priorities, emergent situations, emergencies, and daily operations; and meet deadlines.
Added 1 hour ago
BC
Client Executive – Real Estate
BFL CANADA
Toronto, ON
- Full-time
…insurance partners in over 140 countries, helping to support their operations both in Canada and…
Added 1 hour ago
BC
Producer/Commercial Insurance-Financial, Professional & Technology Services
BFL CANADA
Montreal, QC
- Full-time
Proactively maintain and develop relationships with partner brokers, clients, and their respective operations.
Added 1 hour ago
I
Group Finance Director
isgSearch
Windsor, ON
- $160,000 to $180,000 CAD / year
- Full-time
A well-established North American manufacturing organization with operations across Canada and the U.S.
Added 1 hour ago
HT
Director, Finance (CSM)
Husky Technologies
Bolton, ON
- Full-time
Serve as the senior finance partner to service leadership, operations, commercial teams, and Customer Success leaders, providing insight and challenge on strategic priorities, business…
Added 2 hours ago
CA
Associate Insurance Advisor II
Co-operators Assurance et services financiers
Chéticamp, NS
- Full-time
Added 2 hours ago
CA
Associate Insurance Advisor
Co-operators Assurance et services financiers
Bonnyville, AB
- Full-time
Added 2 hours ago
CA
Associate Insurance Advisor II
Co-operators Assurance et services financiers
Kelowna, BC
- Full-time
Added 2 hours ago
CA
Senior Group Retirement and Savings Sales & Service Representative
Co-operators Assurance et services financiers
Regina, SK
- Full-time
Take ownership of escalated items keeping Account Executives informed as appropriate. Work with Administration and Operations team as needed to ensure a successful resolution is achieved.
Added 2 hours ago
PV
Hospital Administrator
P3 Veterinary Partners
Timmins, ON
- Full-time
…analyze and make effective actionable decisions that impact operations including, but not limited to, asset purchases, new hires, rate changes, and conflict…
Added 2 hours ago
TM
Director, Strategic Planning, Operations and Administration
Toronto Metropolitan University
Toronto, ON
- Full-time
We are currently seeking a Director, Strategic Planning, Operations and Administration to join our team. This role will provide effective strategic leadership of financial planning and…
Added 2 hours ago
BT
U.S. Corporate Tax Partner
Baker Tilly Canada
Toronto, ON
- Full-time
Client profile: US corporations, Canadian companies with US operations
Added 3 hours ago
Lead Analyst - Product and Industry Practice
Altimetrik
Vancouver, BC
Good understanding of banking operations, compliance, and regulatory processes.
Added 5 hours ago
RB
Assistant Branch Manager Intern
Royal Bank of Canada
Pointe-Claire, QC
- Full-time
Added 6 hours ago
SM
Storeperson
Stevenson Memorial Hospital
Alliston, ON
- Full-time
Added 6 hours ago
A
Senior Manager, Strategic Partnerships – Japan Partnerships (Tokyo-based)
Agoda
Toronto, ON
- Full-time
You will work cross-functionally with teams across Commercial, Marketing, Product, Finance, Legal, Analytics, and Operations to bring partnership opportunities from idea to execution and…
Added 6 hours ago
A
Senior Manager, Strategic Partnerships – Japan Partnerships (Tokyo-based)
Agoda
Vancouver, BC
- Full-time
You will work cross-functionally with teams across Commercial, Marketing, Product, Finance, Legal, Analytics, and Operations to bring partnership opportunities from idea to execution and…
Added 6 hours ago
Transit Revenue Contract Coordinator
City of Edmonton
AB
Added 7 hours ago
HT
Director, Finance (CSM)
Husky Technologies
Bolton, ON
- Full-time
Serve as the senior finance partner to service leadership, operations, commercial teams, and Customer Success leaders, providing insight and challenge on strategic priorities, business…

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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