Job description

The short version 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. Today that gets done. It gets done through a mix of partners, internal tooling, and manual work, and it holds together well enough that merchants ship. That's the problem. "Well enough" is not a product, and it isn't a moat. 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. About Portless Portless is changing the face of global e-commerce. 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. Why we need this role now • 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. • Build, buy, or partner is an open question with real money behind it. Some of this capability is genuinely commoditized and should be bought. Some of it is close enough to our core that owning it is a differentiator. Nobody has done the work to draw that line and defend it. • 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. We're operating at a scale where that's now hundreds of thousands of SKUs. • The manual work is real and it's growing. Audits, escalations, chasing merchants for missing data, gating SKUs that aren't ready. Our ops and CS teams absorb this today. Product should be removing it, not watching it scale. • Merchants can't see any of it. 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. What you'll own The end-to-end compliance flow. Not one feature area. 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. You'll be the person who can hold the entire flow in their head and see where it breaks. The strategy, and the case for it. What Portless owns, what we buy, and what we partner for. This is a genuine open decision with strong 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. Prevention over cleanup. 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. The merchant-facing product. 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. Partner strategy and integration. Evaluating what's available in the market, deciding who we work with and for what, and owning the relationship from the product side. What success looks like First 90 days • 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 • A written point of view on build versus buy versus partner, with the reasoning and the tradeoffs, ready to be argued with • The top compliance risks quantified in orders and dollars, sequenced First 6 months • 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 • Meaningful manual work removed from ops and CS • Merchants can see and act on their own compliance status • Compliance is something sales can sell, not just something we have to do What we're looking for Product craft first. 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. Given a messy end-to-end process, you can map where information originates, where it degrades, and where the leverage is • You are fluent in your own data. You check claims against what actually happened rather than asserting them • You've made build-versus-buy calls before and lived with the consequences • You write well. Written strategy, decision docs, and specs are the primary output of this job • You can hold a position under pressure from people who know the domain better than you do, and change it when the evidence says so Industry experience. • You've worked in cross-border commerce, logistics, fulfillment, or supply chain, as a product manager or in a closely adjacent role • 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 • We are not looking for a customs specialist. You will not be writing per-country duty rules. You need enough fluency to be credible with partners, carriers, and our own experts, and the judgment to know when to bring in someone deeper How you work. • You'll be forward-deployed. Close to merchants, close to warehouse and China ops, close to the escalations. Not behind a backlog • You work off one canonical roadmap alongside the rest of product. No side decks, no personal trackers • You partner cross-functionally by default: product, engineering, finance, operations, CS, and merchants themselves • You look for the systemic version of the problem. One merchant's issue is usually twenty merchants' issue What this role is not • Not a trade counsel role. You are not our lawyer and we won't ask you to be • Not a compliance analyst role. You are not auditing shipments by hand. You are building the system that makes that unnecessary • Not a single-feature role. If you want a well-defined slice with clear boundaries, this isn't it. The scope is the whole flow, and part of the job is deciding where the boundaries should be How we work 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 "0 to 1" matters most for this role. There is no existing compliance product to inherit. You're defining what it should be. Apply Tell us about a time you owned a messy end-to-end process and made a real call about what to build versus what to buy. What you decided, what you got wrong, and what you'd do differently. That tells us more than a résumé will. Portless is an equal opportunity employer.

Requirements

Must-haves

The short version
That's the problem. "Well enough" is not a product, and it isn't a moat.
We're hiring a Senior Product Manager to own that.
Product craft first. 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. Given a messy end-to-end process, you can map where information originates, where it degrades, and where the leverage is
You are fluent in your own data. You check claims against what actually happened rather than asserting them
You've made build-versus-buy calls before and lived with the consequences
You write well. Written strategy, decision docs, and specs are the primary output of this job
You can hold a position under pressure from people who know the domain better than you do, and change it when the evidence says so
Industry experience.
You've worked in cross-border commerce, logistics, fulfillment, or supply chain, as a product manager or in a closely adjacent role
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
How you work.
You'll be forward-deployed. Close to merchants, close to warehouse and China ops, close to the escalations. Not behind a backlog
You work off one canonical roadmap alongside the rest of product. No side decks, no personal trackers
You partner cross-functionally by default: product, engineering, finance, operations, CS, and merchants themselves
You look for the systemic version of the problem. One merchant's issue is usually twenty merchants' issue
What this role is not
Not a trade counsel role. You are not our lawyer and we won't ask you to be
Not a compliance analyst role. You are not auditing shipments by hand. You are building the system that makes that unnecessary
Not a single-feature role. If you want a well-defined slice with clear boundaries, this isn't it. The scope is the whole flow, and part of the job is deciding where the boundaries should be
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:

Nice-to-haves

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Application prep

Use the role’s language and application details while tailoring your materials.

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rest

Platform: workable
Effort: medium