Senior Product Manager

We Are Rosie

Senior Product Manager building AI-powered tools for We Are Rosie’s freelance marketing marketplace. Owning discovery, delivery, metrics, and operational automation across teams.

Posted 8/15/2026full-timeRemote • 🇺🇸 United StatesSeniorWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in product management with a focus on AI features, including user research, data analysis, and stakeholder collaboration. Proficient in defining success metrics, automating processes, and managing product tradeoffs in a marketplace environment.

Highest-signal resume keywords

Product Management ExperienceAI Feature DevelopmentUser Research and Data AnalysisStakeholder Communication AutomationMarketplace Product Knowledge

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Product Loop DevelopmentPrompt EngineeringToken Cost ManagementSpreadsheet SkillsSystem Architecture Understanding

Soft Skills

Proactive Problem SolvingTrust with Engineering PartnersBias Toward ActionComfort with Ambiguity

Tools & Technologies

Large Language ModelsAgentic WorkflowsAPI Capabilities

Industry Keywords

Marketplace ProductsTwo-Sided Network ProductsP&L ImpactUnit EconomicsChange Management

About the role

Key responsibilities & impact

Own the roadmap, priorities, tradeoffs, and results for a product work stream
Run structured discovery cycles using user research, data analysis, and stakeholder input
Translate insights into actionable specifications and prototypes
Collaborate with engineering to scope, estimate, and ship initiatives on time
Ship product features built on large language models and agentic workflows
Own AI product tradeoffs including model selection and migration, prompt and context design, token cost, latency, evaluation, and failure modes
Identify manual, spreadsheet-bound work across Rosie Ops, Client Experience, and Finance and replace it with automations and agents
Define and track success metrics for product initiatives
Build alignment with Sales, Marketing, Operations, Client Experience, and Finance
Set communication cadences and automate stakeholder updates
Understand the We Are Rosie marketplace and make decisions serving both Rosies and brands
Proactively flag risks, bring solutions, manage work independently, and raise team capability

Requirements

What you’ll need

2–5 years of product management experience, ideally with marketplace, platform, or two-sided network products
Experience building a complete product loop: discovery, prototype, user validation, shipping, measurement, and iteration
Experience shipping AI features to production for customers or colleagues
Knowledge of context windows, token costs, prompt engineering, retrieval, fine-tuning, agent loops, output-quality evaluation, and inaccurate model output handling
Record of moving teams to AI through training, playbooks, change management, and adoption by non-technical colleagues
Ability to produce clear problem framing, sound scoping, and effective AI-drafted PRDs, tickets, specifications, and status summaries
Ability to establish communication rhythms and automate stakeholder updates
Experience working with finance teams and understanding product impact on P&L, unit economics, and revenue
Strong spreadsheet skills
Understanding of system architecture, API capabilities, and limitations
Ability to distinguish when to challenge technical constraints and when to find workarounds
Comfort with ambiguity and resource constraints
Track record of trust with engineering partners
Bias toward action and execution
Ability to work independently, proactively flag risks, and bring solutions

Benefits

Comp & perks

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
Opportunity to join a truly incredible team at a company that is building the future of work