Product Manager

Flossy

15h

About The Position

Flossy is seeking a highly technical, entrepreneurial Founding Product Manager to build products from the ground up, focused on AI agents that can perform increasingly complex work typically handled by experienced employees. The role owns major product initiatives from discovery through launch and iteration, combining customer engagement, opportunity identification, technical collaboration, and real-world performance measurement. The Product Manager will shape AI-powered experiences across communication, scheduling, insurance, billing, and operational workflows; develop tools for businesses to configure, monitor, evaluate, and improve AI agents; create workflows that turn conversations and operational data into recommendations and automated actions; connect agents to external systems, APIs, and real-time business data; and take new capabilities from prototype to production. The position offers meaningful autonomy, direct customer access, and influence over foundational product decisions. The role also includes shaping Flossy's product organization and its approaches to discovery, prioritization, experimentation, and product development as the company grows. Flossy describes itself as a small, fast-moving team that values ownership, curiosity, speed, customer learning, and product quality.

Requirements

At least 5 years of relevant experience in product management, engineering, or founding and building technology products.
Track record of shipping impactful products, including taking ideas from zero to one.
Strong technical acumen and comfort discussing APIs, data models, system architecture, and AI capabilities with engineers.
Strong product judgment, including identifying underlying customer problems, distinguishing core requirements from edge cases, and making thoughtful tradeoffs.
Hands-on approach and enjoyment of prototyping, experimenting with tools, and bringing ideas to life quickly.
Strong analytical skills and experience using data to inform product decisions and measure results.
Excellent communication skills and ability to work closely with technical teams, customers, and company leadership.
Comfort operating in ambiguous, fast-moving environments where priorities evolve.

Nice To Haves

Experience building AI-native products, particularly LLM-powered agents, conversational AI, or workflow automation.
Experience with agent evaluation, prompt engineering, model performance, or human-in-the-loop systems.
Experience building enterprise SaaS platforms, developer tools, or products with complex integrations.
Previous experience as a founder or early employee at a high-growth startup.
Experience with healthcare technology or other industries with complex operational workflows.

Responsibilities

Own product strategy and execution, including vision, roadmap, and success metrics for major platform areas, from concept through launch, adoption, and continuous improvement.
Work directly with customers to understand business operations, workflow problems, and opportunities worth solving.
Translate complex problems into clear product requirements, prototype solutions, evaluate technical tradeoffs, and collaborate closely with engineers to ship high-quality products.
Define AI-native experiences, including how people interact with agents, how agents coordinate, and how businesses maintain visibility and control over automated workflows.
Use product analytics, experiments, customer feedback, and agent performance data to measure results and improve outcomes.
Contribute to Flossy's product discovery, prioritization, experimentation, and development practices as an early team member.
Build AI-powered experiences coordinating specialized agents across communication, scheduling, insurance, billing, and operational workflows.
Design tools that enable businesses to configure, monitor, evaluate, and continuously improve AI agents.
Create intelligent workflows that turn conversations and operational data into recommendations and automated actions.
Connect agents to external systems, APIs, and real-time business data.
Develop product capabilities from early prototype through production.