Flodesk - Sr. Product Manager, AI
Requirements
• You have shaped or meaningfully improved real LLM or agentic products, with evidence that your work improved user outcomes or product quality • You have practical knowledge of prompts, context, tools, agent behavior and evaluation, and understand how those parts interact in a production experience • You are hands-on with prompt iteration, evaluation tools and trace review, and are comfortable working with JSON, schemas and structured outputs • You have strong product judgment and can turn ambiguous member needs into clear behavior, quality definitions and testable hypotheses • You bring experimental rigor. You can design representative test sets, build useful failure taxonomies and separate signal from anecdote • You think in systems and reusable patterns. You can make today's email experience better without hard-coding assumptions that make tomorrow's surfaces harder to build • You communicate clearly across technical and non-technical disciplines and can make sound tradeoffs involving member value, quality, latency, reliability and cost • Owned AI product behavior, conversation design, computational linguistics or prompt systems • Built content-generation, creative or marketing tools • Used Langfuse, Braintrust or comparable evaluation and observability platforms • Worked on products for small businesses, creators or marketers • What we bring • Tier 1 city residents: $165,000 - $200,000 • All other locations: $150,000 - $185,000 • Fully paid health insurance for individual coverage • 16 weeks paid parental leave for non-birthing parents; 22 weeks paid maternity leave for birthing parents • Unlimited flexible time off • 401(k) match (US employees only) • $1,000 annual stipend for learning and development
Responsibilities
• Manage member-facing AI behavior across prompt-to-create, agentic editing and future jobs such as segmentation, scheduling, analytics and recommendations • Create, test, version and document prompts and agent instructions, with a clear record of what changed, why it changed and how behavior improved • Define what context, member data, tools and product state the AI needs to do a job well, then translate those needs into clear requirements and acceptance criteria • Own Flodesk's AI evaluation practice, including representative datasets, behavioral scenarios, scoring rubrics, regression coverage and human review • Run the recurring evaluation and quality-monitoring process independently using available tools. Set baselines and release gates for prompt, model and agent changes • Review traces and complete AI interactions to diagnose whether a failure most likely comes from the prompt, context, model, tool, product structure or implementation. Fix what you own and turn the rest into clear, actionable changes for engineering • Turn member research, support feedback, analytics, production failures and domain expertise into priorities, experiments and durable regression cases • Own the day-to-day product direction and learning agenda for Flodesk's AI experience. Partner with product, design, marketing, copy and engineering to encode a coherent Flodesk point of view into the system
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