Head of Product at Medium

Advocate is transforming how Americans access government benefits. Using cutting edge AI technology, we're reducing months long disability application processes to days, helping vulnerable citizens get the support they deserve. After 2.5 years of rapid growth, we have proven the technology works. Now, we need a product visionary to define how this technology scales to reach millions.

We are seeking a Head of Product who sees the future of government interaction not as forms and queues, but as a fluid, intelligent conversation. This is an executive role. You will sit at the leadership table, partnering directly with our CEO and CTO to define what we build and why, reimagining the product landscape in an AI first world.

This role is for a strategist who finds clarity in ambiguity. You understand that a roadmap is not a list of features in Jira, but a strategic narrative that bridges user needs, technical possibility, and commercial growth. You will design the vehicle that carries our AI technology into new markets and channels.

You will own the product vision, strategy, and design. You will work lock step with the CEO on the company's long term vision, translating high level mission goals into concrete product reality. You will collaborate intimately with engineering and marketing, but you are not a project manager. We do not need someone to groom backlogs or nag engineers about dates; we need someone to invent the future of the platform, identify new distribution channels, and design experiences that feel like magic.

• Executive Vision & Strategy: As a key member of the executive team, you will partner with the CEO to shape the future of the business. You will look months ahead, defining how our product evolves to dominate the market. You aren't just executing a roadmap; you are defining the strategic trajectory of the company.
• Channel & Growth Architecture: We have a core product that works. Your job is to figure out how to package and deploy it through new sales channels. You will conceptually design how our platform integrates with partners, legal firms, and healthcare providers, creating product loops that drive their own growth.
• Activation & Onboarding Excellence: You own the complete user journey from landing page through activation. This is not a handoff-it's a critical partnership with marketing where product decisions directly impact conversion and retention. You will work closely with our Head of Marketing to ensure the onboarding experience delivers on the promise of our marketing, running continuous tests and optimizing the flow that turns interested visitors into successful users. The marketing team's results depend on what happens after the click, and you're accountable for making that experience exceptional.
• AI Native Product Discovery: Just as our engineers use AI to code, you use AI to think. You don't just guess at user sentiment; you build AI loops to analyze thousands of interactions instantly. You don't write static PRDs; you treat AI as a co author to simulate user flows and edge cases before a single line of code is written.
• Symbiosis with Engineering: You speak the language of trade offs. You understand that "perfect" is the enemy of "shipped," but "sloppy" is the enemy of "scale." You will work with the CTO to align technical architecture with product goals, ensuring that what we build today supports the complexity of tomorrow.
• Design & User Experience: You may not be a pixel pusher, but you possess high design fidelity. You understand that in an AI product, the UX is the trust layer. You will ensure that every interaction-whether human or machine-feels human centric, transparent, and incredibly simple.

Essential Background: You are a product leader who has taken a complex technical product from early traction to multi channel scale. You have experience not just optimizing funnels, but inventing entirely new ways for a product to exist in the market. You understand that activation metrics are where marketing meets product reality, and you've successfully owned this critical handoff. You have a strong grasp of unit economics and business strategy.

Strategic, Not Administrative: You view Product Management as a discipline of invention and strategy, not administration. If your superpower is "keeping tickets moving," this is not the role for you.

First Principles Thinker: You don't build things because "that's how SaaS works." You look at the problem-vulnerable citizens navigating bureaucracy-and design the most direct path to the solution, even if it defies convention.

Commercial Fluency: You understand that a great product must be a great business. You can envision how technical features translate into new revenue streams and sales channels. You know that every dollar marketing spends to bring users in must be justified by what happens in the product.

Cross Functional Partnership: You see marketing as a strategic partner, not a separate function. You understand that messaging consistency from ad to onboarding is what builds trust, and you proactively align with marketing on activation goals and metrics.

High Agency & Ownership: You don't wait for permission or data perfection. You form a thesis, test it, and drive it. You own the outcome of the product, from the user's delight to the bottom line.

AI Partnership: You have integrated AI into your personal workflow. You use LLMs to draft strategies, analyze market data, and stress test your logic. You understand the capabilities and limitations of current AI models and build product strategies that leverage them realistically.

Technical Respect: You don't need to code, but you must understand the implications of architectural decisions. You can sit with the CTO and understand why a specific database choice impacts the future product roadmap.

You are not a Scrum Master. You are not a "Feature Factory" manager who measures success by output volume. You are not someone who views the post click experience as "someone else's problem." You are not afraid of a blank whiteboard.

• Executive Leadership: A seat at the table defining the strategy for a company transforming government services.
• Direct Impact: Ownership of a platform that will serve millions of Americans.
• Elite Team: Collaboration with a high performing engineering, marketing, and leadership team where your vision becomes reality.
• Autonomy: Freedom from "process theater"-focus on strategy, design, and growth.
• Compensation: Competitive compensation package with fair equity.
• Culture: Remote first culture with regular team gatherings.

Join us in building the platform that will revolutionize government services.