Every package Portless ships crosses a border, and every one of them carries a set of compliance obligations: how the product is classified, what value is declared, what duties and taxes apply, and what each destination market requires. It gets done through a mix of partners, internal tooling, and manual work, and it holds together well enough that merchants ship. Compliance should be one of the strongest reasons a brand chooses Portless over anyone else. Getting there requires someone who can look at the whole flow end to end, decide what we own versus what we source from the market, and build a coherent system out of what is currently a set of individually reasonable decisions. We're hiring a Senior Product Manager to own that. By decoupling brands from traditional, expensive domestic warehousing, we let e-commerce companies ship directly from manufacturing hubs to global consumers in as little as three to five days. We move packages to 75+ countries for hundreds of DTC brands, with 2.5 million+ cross-border packages shipped, 99.8% pick-and-pack accuracy, and 98% on-time delivery. We're a small, remote-first team, and the work you do here shows up in a merchant's business within weeks. Compliance has no clear product direction. We work with multiple compliance partners and we've built real integration infrastructure to support them. What we haven't decided is what Portless itself offers as a compliance product, and that decision is now blocking several others. The data problem is upstream of everything. Compliance decisions depend on product data that originates in merchant catalogs of wildly varying quality, then flows through several systems before it reaches a customs declaration.



Every downstream problem traces back to where that data came from and whether anyone validated it. Audits, escalations, chasing merchants for missing data, gating SKUs that aren't ready. They don't know their compliance exposure, they can't self-serve a fix, and we can't show them the value we're providing. That's a product gap and a commercial one. The end-to-end compliance flow. The whole path from merchant catalog to cleared shipment: where the data originates, how it's validated, where it's enriched, what's stored, what gets declared, and what happens when something is missing or wrong. This is a genuine open decision with robust opinions on multiple sides, and we'll expect you to form a view, argue it with data, and then be accountable for it. Data quality as a product outcome. Classification coverage and accuracy, declared values, country of origin, and the rest, treated as tracked metrics with systems behind them rather than a recurring cleanup project. The mechanisms that stop a non-compliant SKU from becoming a stuck shipment or a wrong invoice: validation at intake, gating, escalation, and the merchant-facing flows that make it easy for a brand to fix their own data. How compliance shows up in the portal, how a merchant understands their own exposure, and how we demonstrate the value we're delivering. This is the piece that turns compliance from a cost center into a reason to choose us.



Evaluating what's available in the market, deciding who we work with and for what, and owning the relationship from the product side. You understand the full flow, including the parts that live in ops and CS rather than in software, and you can explain where every input comes from The top compliance risks quantified in orders and dollars, sequenced A compliance strategy the company has aligned on, with a roadmap behind it Data quality tracked as a metric that is measurably improving, owned by a system rather than a person Merchants can see and act on their own compliance status Compliance is something sales can sell, not just something we have to do This is the bar we're least flexible on. ~5+ years in product management with real ownership of a complex, data-heavy domain ~ You think in systems and data flow. You are fluent in your own data. You check claims against what actually happened rather than asserting them ~ You've dealt with compliance at a strategic level: you understand what classification, declared value, duties, and destination requirements mean for a business, and you've had to make product decisions around them You will not be writing per-country duty rules. No side decks, no personal trackers Not a compliance analyst role. You are building the system that makes that unnecessary Remote-first, with meaningful Eastern Time overlap. Life-first: we care about velocity and ownership, not hours or visibility. Our values are the actual operating system here, not wall art: Extreme Ownership
· 0 to 1
· Champion the Customer
· Going Deep
· Be Kind and Caring
· Velocity Compounds "There is no existing compliance product to inherit.

📌 Remote Senior Cryptocurrency Platform Product Manager (Canada)
🏢 Portless
📍 Canada