About We Are Rosie We Are Rosie is redefining how marketing talent works — connecting exceptional freelance marketers ("Rosies") with the world's most ambitious brands. Our platform is the engine behind this mission: matching talent, enabling seamless collaboration, and giving Rosies the infrastructure to do their best work. The product team is responsible for making that engine run. The Role We're looking for a Senior Product Manager who is ready to own. You'll lead end-to-end delivery of core platform initiatives, from discovery through launch through measurement. You're the connective tissue between engineering, design, operations, and the business — and you know how to make things happen in a fast-moving, resource-constrained environment. A significant part of this role involves AI. You'll ship product features built on large language models, and you'll use AI to improve how internal teams work. We're looking for someone with production experience (internal tools included!), not just familiarity with the tools. This is a high-accountability, high-execution builder role. You'll set direction for your area, prioritize ruthlessly, and ship work that moves the business. Responsibilities - Product area leadership — Full accountability for your work stream: roadmap, priorities, tradeoffs, and results. - Discovery and delivery — Run structured discovery cycles (user research, data analysis, stakeholder input) and translate insights into clear, actionable specs and prototypes. Collaborate with engineering to scope, estimate, and ship on time. - AI product delivery — Ship features built on LLMs and agentic workflows, and own the tradeoffs underneath them: model selection and migration, prompt and context design, token cost per transaction, latency, evaluation, and failure modes. You can explain to Finance what a feature costs to run per user, and to Engineering why one model fits a given job better than another. - AI for internal operations — Identify manual, spreadsheet-bound work across Rosie Ops, Client Experience, and Finance, and replace it with automations and agents. Success is measured in hours returned, error rates reduced, and single-person dependencies removed. - Metrics ownership — Define success metrics for your initiatives and track them. You can speak confidently to the why behind prioritization decisions using data. - Stakeholder alignment — Build trust and earn alignment with cross-functional partners (Sales, Marketing, Operations, Client Experience, and Finance). You manage up, sideways, and across — proactively, not reactively. You set the cadence and rhythm of communication; stakeholders know what to expect and when, without asking. - Platform stewardship — Deeply understand the WRR marketplace — both Rosie experience and brand-side workflows — and make decisions that serve both sides of the market. Requirements - Product management foundation — 2–5 years of product management experience, ideally with marketplace, platform, or two-sided network products. - A product loop you built yourself — Discovery → prototype → validate with users → ship → measure → feed what you learned into the next cycle. We want to hear about the loop, not one launch: how fast it turns, what you changed after the data came back, and what you'd do differently on the third pass. - AI features shipped to production — We want to hear about something customers or colleagues actually used: what the model was doing, why you selected it, what you tried that didn't work, what it cost to run at volume, and what it changed for the business. Specifics matter more than scale — "reduced match-review time from 40 minutes to 6 across 300 weekly reviews" is the level of detail we're looking for. - Fluency in the mechanics — Context windows, token cost and how to reduce it, prompt engineering vs. retrieval vs. fine-tuning, when an agent loop is worth the added complexity, how to evaluate output quality at scale, and how to handle inaccurate model output. You don't need to have trained a model, but you should be able to explain why inference costs changed and what to do about it. - A record of moving teams to AI — Running training, writing playbooks, working through resistance, and getting non-technical colleagues using AI in their daily work. This is a change management skill as much as a technical one. - Communication executed with leverage — You can write a crisp PRD, but we don't expect you to be typing them. PRDs, tickets, specs and status summaries should be AI-drafted from your inputs, with your judgment applied to what goes in and what ships. What we're hiring for is the thinking underneath: clear problem framing, sound scoping, and the ability to spot when a generated spec is vague, wrong, or missing the constraint that matters. You'll be accountable for more documentation than any PM could hand-write, and it should still be good. - Communication rhythms you set — You don't wait to be asked for status updates; you set the cadence so stakeholders stay informed and aligned without constant check-ins. Much of this should be automated — you design the system that produces the updates rather than assembling them by hand each week. - Business judgment — You've worked with finance teams, understand how product decisions cascade into P&L, and can prioritize trade-offs based on unit economics and revenue impact. You're dangerous with a spreadsheet. - Technical judgment — You understand system architecture, can discuss API capabilities and limitations, and know when to push back on "that's not possible" vs. when to find a workaround. You don't need to code, but you think like someone who does. - Comfort with ambiguity and resource constraints. - A track record of trust with engineering partners. - Bias toward action — you default to clarity and execution, not analysis paralysis. - You've worked with finance teams, understand how product decisions cascade into P&L, and can prioritize trade-offs based on unit economics and revenue impact. You're dangerous with a spreadsheet. - You understand system architecture, can discuss API capabilities and limitations, and know when to push back on "that's not possible" vs. when to find a workaround. You don't need to code, but you think like someone who does. What "Senior" Means Here At WRR, Senior PM means you don't need to be managed — you manage the work . You proactively flag risks, bring solutions rather than problems, and hold yourself and your team to a high bar. You earn trust through consistency, not noise. Stakeholders know your rhythm: weekly updates land on Friday, roadmap reviews happen the second Tuesday of the sprint, blockers get surfaced 48 hours before they derail timelines. That reliability is the signal that you're in control of your area and your partners can plan around you. Senior here also means raising the capability of the people around you. We care as much about what your team can do six months after you arrive as about your individual output. This role is the foundation for product leadership at WRR. Perks & Benefits A yearly stipend for professional and personal development; 25 PTO days + 4 Volunteer PTO days per year; medical, dental, and vision insurance; paid parental leave; remote work stipend; matching 401K; and an opportunity to join a truly incredible team at a company that is building the future of work. OUR VALUES Treat People Like People - Seeing the value in all people’s unique lives, experiences, and perspectives is what drives us. Start With Why - Asking “Why” makes our team curious first so we get to better solutions. When we make a decision, we take the time to explain the “Why”’ behind our actions. Transparency is clear and it’s kind. Speak With Actions - Trust isn’t given, it’s earned. We prove our reliability and trustworthiness to each other, our clients, and our Rosies by showing up and doing what we say we will — through small interactions and big moves. Bring Tenacity - The path isn’t always an easy one, but our team chooses to be unwavering in our goal. We’re resilient, determined, and stubborn when necessary. That’s the fire it takes to get things done. Make it Better - From changing old processes to disrupting the marketing industry, we know there is room to make it better. We strive to find those improvements and push them to reality. We Are Rosie is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, age, national origin, ancestry, physical or mental disability, medical condition, pregnancy, genetic information, gender, sexual orientation, gender identity or expression, veteran status, marital status, or any other status protected under federal, state, or local law. Accessibility Statement We Are Rosie is committed to an inclusive and accessible recruitment process. Please let us know if you need accommodations during the application or interview stages, and we will assist you. We aim to provide an equitable experience for all candidates to showcase their skills. For questions about accessibility, please contact us at POps@wearerosie.com. We look forward to welcoming diverse talent to our team.

Senior Product Manager

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