Senior Product Manager

We Are Rosie connects exceptional freelance marketers with ambitious brands through a platform that supports talent matching and collaboration. The Senior Product Manager will own end-to-end delivery of core platform initiatives, lead discovery and prioritization, and ship AI-powered features and internal automations. The role partners across engineering, design, operations, finance, and business teams while owning metrics, stakeholder alignment, and marketplace platform stewardship.

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:

• 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
• Product management foundation — 2–5 years of product management experience, ideally with marketplace, platform, or two-sided network products