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Senior Product Manager - Billing & Entitlements

Oscer

Oscer

Product
Melbourne VIC, Australia · Sydney, NSW, Australia · Melbourne, VIC, Australia · Sydney, NSW, Australia
Posted on Oct 2, 2025

Location

Melbourne HQ or Sydney

Employment Type

Full time

Department

Product

Howdy, we're Heidi 👋

“The AI startup growing faster than Canva"

That’s what the Financial Review called us. In one year, we hit $15M ARR and became one of the fastest-growing companies in the world.

Two years ago, we pivoted from broad healthcare AI to building Earth’s finest clinical exoskeleton. Today we support over 2 million patient sessions weekly across 50+ countries. Hundreds of thousands of clinicians use Heidi to complete documentation.

Our mission is simple: double care capacity by eradicating non-clinically-useful busywork.

We've found product-market fit with individual clinicians through our freemium medical scribe, transforming unstructured clinical visits into structured text artefacts. Clinicians and organizations quite like it. Now, we embark upon consuming more than just documentation. Every new job a clinician delegates to Heidi makes patients feel more attended to, cleans up health system logjams, and lets clinicians be clinicians again.

That’s where you come in.

The Role

We’re looking for a Senior Product Manager to lead our Billing & Entitlements platform. This role is foundational: you’ll own the evolution of our enterprise billing, automating processes and creating a seamless experience that connects enterprise and PLG customers into a single system.

You’ll partner with Finance, Engineering, CS, and Sales to design billing and entitlement systems that scale globally. From invoicing to entitlements logic to admin clarity, you’ll ensure Heidi’s billing foundation is reliable, compliant, and a joy to use.

This is the infrastructure that powers how customers buy, pay, and unlock Heidi at scale.

What you’ll do

  • Define and own the strategy and roadmap for Heidi’s Billing & Entitlements platform.

  • Build integrations that unify enterprise offline billing with self-serve PLG flows.

  • Deliver subscription management, invoicing, entitlements services, and payments integration with Stripe and other vendors.

  • Partner with Finance, CS, and Sales to ensure billing flows are accurate, compliant, and scalable.

  • Collaborate with Engineering to design integrations, run spikes, and build infra that scales 100x.

  • Shape admin and user experiences that make billing and entitlements transparent and trustworthy.

What you’ll need

  • 5+ years PM experience, with at least 2+ in billing, payments, or entitlements platforms.

  • Experience integrating enterprise offline billing with online/Stripe PLG systems.

  • Track record of delivering billing/entitlement systems at scale (e.g. Zuora, Stripe, PayPal, etc.).

  • Strong ability to cut through competing asks (customers, sales, finance) and focus on what truly matters.

  • Ability to influence and align Finance, Legal, CS, and GTM stakeholders.

  • Platform mindset — build for today, but design for hypergrowth.

If we’d worked together the last 6 weeks, you’d have:

  • Run a discovery sprint with Finance, CS, and Sales to map offline enterprise billing and payment flows and pain points.

  • Scoped how entitlements should unify PLG Stripe billing with enterprise contract enforcement.

  • Partnered with Eng to spike an integration bridging offline invoices with Stripe subscription management.

  • Drafted a 2-quarter roadmap for Billing & Entitlements to split into its own pod.

  • Unblocked a customer’s billing escalation by clarifying proration and entitlement behavior mid-contract.

Why Heidi?

Our health systems hurt everybody. Systems are log-jammed, clinicians' lives degrade in quality, and patients churn through the meat-grinder.

This is neither a special nor interesting insight.

But it means we’re solving a real problem. Hundreds of thousands of clinicians use Heidi. Every clinician using Heidi gets hours back in their day. That’s the starting point to build the product of your dreams: immense distribution, and a world of potential.

You’ll join a team that doesn’t celebrate fundraise milestones or glossy PR. We live and breathe the pain of modern health systems and won’t rest until we’ve exacted the change we’d like to see.

The bad news: it’s not an easy job — you’ll tear your hair out more than once. Modern tech concepts don’t transpose easily into healthcare. The lows are really low.

The good news: you’ll trust and admire everyone you work with, and know you’re doing the defining work of your career. The highs are blindingly high.

Heidi will take care of you: equity, growth, wellness perks, and the chance to progress fast if you’re an A-player.