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VP of Product

Job in Toronto, Ontario, M5A, Canada
Listing for: Portless
Full Time position
Listed on 2026-02-23
Job specializations:
  • Business
    Ecommerce, Operations Manager
  • IT/Tech
    Ecommerce
Salary/Wage Range or Industry Benchmark: 100000 CAD Yearly CAD 100000.00 YEAR
Job Description & How to Apply Below
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About Portless
Portless is redefining global fulfillment for fast-growing DTC brands. We enable merchants to ship direct-from-factory with Amazon-level speed, reliability, and transparency—without the traditional complexity of cross-border logistics. Our customers are some of the most innovative consumer brands in the world, and they expect a world-class experience across onboarding, integrations, fulfillment, tracking, exceptions, and support.

Opportunity
We are looking for a strategic yet deeply operational product leader who thrives in the messy reality of complex, real-world systems. You will:

Unify product, data, operations, engineering, and customer success into a cohesive roadmap

Build a user experience that feels inevitable to fast-growing eCommerce brands: intuitive onboarding, seamless integrations, proactive visibility, and flawless fulfillment

Bring clarity, structure, and scale to a hybrid business where digital interfaces, warehouse operations, global carriers, and internal teams all must work in lockstep

What You’ll Own

Product Strategy & Vision

Define and own the multi-year product roadmap aligned to company strategy and merchant needs

Build a vision for a frictionless, end-to‑end merchant experience—from contract → integration → inbounding → fulfillment → tracking → exception handling

Combine operational reality with ambitious customer experiences to create a category‑defining product

Leadership & Cross‑Functional Collaboration

Lead and grow the Product and Design team

Partner deeply with Engineering, Operations, Customer Support, and Sales/Partnerships

Create product processes that scale: requirements, prioritization, discovery loops, beta programs, and feedback systems

Customer Experience & Merchant Success

Own the quality of the merchant journey end‑to‑end, including onboarding, integrations, workflows, and visibility

Translate high‑touch customer expectations (DTC brands doing $100k+ monthly) into scalable product and support systems

Develop world‑class merchant dashboards, exception workflows, and tools for proactive visibility

Operational Excellence & Tooling

Build and refine internal tools for Operations, CX, and Partner teams—ensuring our people are as empowered as our customers

Understand warehouse, cross‑border, and carrier operations well enough to design systems that improve reliability, SLAs, and efficiency

Drive automation in exception handling, carrier selection, tracking, and compliance

Data, Insights, and Quality

Establish metrics and KPIs that measure reliability, customer experience, operational efficiency, and product adoption

Partner with Data to instrument the platform for real‑time visibility

Build a culture of measurement and hypothesis‑driven iteration

Who You Are
Must‑Haves

7‑10+ years of product leadership, with at least 3+ years in tech‑enabled operations, logistics, or marketplace environments

Proven ability to build products that orchestrate humans + software + physical world processes

Experience delivering highly reliable, SLA‑based, multi‑step workflows

Demonstrated success working with customers who have high expectations, complex integrations, and real‑money consequences

Strong systems thinker—comfortable mapping 10+ interconnected subsystems and reducing complexity into clear product decisions

Exceptional communicator able to influence engineering, operations, commercial teams, and executive stakeholders

Obsession with customer experience, from pixel‑level detail to warehouse operational constraints

Nice‑to‑Haves

Experience with eCommerce, fulfillment, or supply chain

Experience with Shopify ecosystem, ERPs, or logistics APIs

Experience scaling product teams from 0 → 1 or 1 → many

Global or cross‑border logistics exposure

What Success Looks Like in 12 Months

A clear, coherent product strategy aligned across engineering, ops, and commercial teams

A significantly improved merchant onboarding and integration experience

A world‑class merchant dashboard with visibility, tracking, and exception management

Reduced operational defects and support touchpoints through better product workflows

A product organization executing predictably with high quality and velocity

Happier, stickier customers who see Portless as a 10x better global fulfillment partner

Why Join Portless?
You’ll be defining the future of global eCommerce logistics—creating a magical experience for brands that want Amazon‑level fulfillment without the Amazon‑level constraints. This role sits at the intersection of software, logistics, data, and world‑class customer service. If you want to build a category‑defining product in a company growing explosively, Portless is the place.

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