Remote Order Entry Jobs in Calgary, AB (NOW HIRING)

LOCATION: Remote anywhere in Canada

Proof is the service-of-process marketplace modernizing how legal documents move through the real world. 10,000 law firms trust us with documents that have legal consequences: a serve has to reach the right person, at the right address, under the right rules, with a court-ready affidavit proving what happened.

That promise may look simple from the outside. Underneath is a multi-sided operating system: law-firm intake, jurisdiction-specific rules, server in-the-field workflows, exception handling, and court-ready affidavits. The product challenge is making all of that complexity feel simple, reliable, and legally safe for the customer.

Law firm customers, from small practices to AmLaw 100, are the center of Proof's growth. Making their experience feel effortless is the most leveraged product surface in the company.

As Product Manager for Law Firm Growth, you'll own the product surface that turns Proof from a useful vendor into a default system of work for every law firm: ordering serves, managing complexity, adopting integrations, and expanding their usage.

You'll report to the CPO and partner closely with engineering, design, and GTM. Your mandate: make Proof easier for law firms to adopt, rely on, and use repeatedly. If you do that well, revenue grows, retention improves, and the operational effort behind each serve goes down.

• End-to-end law firm experience. You'll own the path from first onboarding through job creation, status confidence, exception handling, and repeat usage — making Proof simple enough to adopt, reliable enough to trust, and valuable enough to become a default workflow.
• Enterprise integrations. We're industry leaders across Filevine, Clio, Litify, MyCase, and more. You'll decide where platform parity matters, where workflow depth matters more, and how product, engineering, and GTM turn integrations into expansion.
• Locate Services and address intelligence. A tiered product around pre-attempt address confidence. Better addresses cut wasted attempts and unlock attach-rate revenue.
• Practical AI in high-stakes workflows. You'll decide where AI can safely reduce effort inside the serve lifecycle — and where accuracy, latency, cost, or legal risk means the product needs stronger guardrails.

• Make it feel effortless. The work is complicated. The product shouldn't feel that way.
• Start with the real workflow. Spend time with law firms, ops, sales, and support until you understand the work well enough to simplify it.
• Use data to find leverage. Pull the funnel apart, form a point of view, run the bet.
• Treat trust as a feature. In legal workflows, speed only matters if the affidavit holds up in court.

We're looking for a PM with range: someone who can understand the messy reality of law-firm work, find the growth leverage inside it, and ship product that compounds. You don't need to be an expert in every surface, but you do need the curiosity and judgment to learn quickly.

You'll be a strong fit if:

• You've shipped complex B2B workflow products where the hard part was understanding the work, not arranging the UI.
• Growth loops are natural to you: activation, retention, expansion, funnel leaks, experiments, and durable product fixes.
• You're data-fluent enough to pull your own numbers, challenge a dashboard, and form a point of view without waiting for an analyst.
• You understand integrations as more than APIs: the demo, the parity expectations, the partner dynamics, and the enterprise sales motion around them.
• You have grounded AI judgment: where it creates leverage, where it creates risk, and how to make it useful instead of ornamental.
• You move quickly without getting sloppy — and you know when one more customer conversation is worth more than one more planning doc.

Bonus points if you have:

• Legal tech, marketplace, or vertical SaaS experience where the workflow is the product.
• Experience with complex enterprise customers in a growth-stage environment, where product, sales, onboarding, and integrations work together to drive expansion.
• Series B/C experience where the surface is expanding faster than headcount.
• Comfort with AI eval workflows — accuracy, latency, cost, drift, model selection.

This probably isn't the right seat if:

• You'd rather manage PMs than ship product. This is an IC role.
• You reach for heavy process before understanding the problem.
• You'd rather hand off customer interviews and the data work than own them.

Proof is gaining market share quickly, and the law firm surface is where the next wave of revenue and retention is built. Integrations are our fastest-growing enterprise entry point, with Locate Services and broader integration parity queued behind them. The surface is expanding faster than coverage can keep up — the next PM compounds that motion.

This role comes with real strategic surface area, direct exposure to leadership, and ownership over the front door of Proof's business. We'd like you to help shape what comes next.

Benefits:

• Full-time, salary position
• Fully remote role, based in Canada
• Flexible time off and holidays
• Equipment provided
• Comprehensive benefits package, including healthcare, dental, and disability insurance

Compensation:

• 135,000 - 185,000 CAD based on experience and location. Must be located in Canada
• Eligible to participate in company bonus plan