Founding Product Manager

About the Role

We're looking for a highly technical, entrepreneurial Founding Product Manager who loves building products from the ground up.

At Flossy, we're tackling a particularly interesting challenge: how do you build AI agents that can reliably perform the work of experienced employees?

A great front desk manager knows more than how to answer the phone. They understand their customers, navigate complicated scheduling and insurance rules, coordinate with colleagues, and know how to handle situations that don't follow a script.

We're building AI systems capable of taking on increasingly complex parts of that work.

As a Founding PM, you'll own major product initiatives from initial discovery through launch and iteration. You'll spend time with customers, identify opportunities for automation, work directly with engineers on technical solutions, and measure how your products perform in the real world.

Your work might include:

• Building AI-powered experiences that coordinate multiple specialized agents across communication, scheduling, insurance, billing, and operational workflows.

• Designing tools that allow businesses to configure, monitor, evaluate, and continuously improve their AI agents.

• Creating intelligent workflows that turn conversations and operational data into recommendations and automated actions.

• Expanding what our agents can do by connecting them to external systems, APIs, and real-time business data.

• Developing new product capabilities and taking them from early prototype to production.

You'll have meaningful autonomy, direct access to customers, and the opportunity to shape foundational product decisions as we grow.

In This Role, You Will

• Own product strategy and execution. Define the vision, roadmap, and success metrics for major areas of Flossy's platform, taking products from concept through launch, adoption, and continuous improvement.

• Work directly with customers. Develop a deep understanding of how businesses operate, where existing workflows break down, and which problems are worth solving.

• Build alongside engineering. Translate complex problems into clear product requirements, prototype solutions, evaluate technical tradeoffs, and work closely with engineers to ship high-quality products.

• Develop AI-native experiences. Help define how people interact with AI agents, how agents coordinate with one another, and how businesses maintain visibility and control over automated workflows.

• Measure what matters. Use product analytics, experiments, customer feedback, and agent performance data to understand what's working and improve outcomes.

• Help shape our product organization. As an early member of the team, contribute to how we approach discovery, prioritization, experimentation, and product development as the company scales.

Your Background Looks Something Like This

• 5+ years of relevant experience in product management, engineering, or founding and building technology products.

• A track record of shipping impactful products, including experience taking ideas from zero to one.

• Strong technical acumen. You're comfortable discussing APIs, data models, system architecture, and AI capabilities with engineers.

• Excellent product judgment. You can identify the underlying customer problem, distinguish important requirements from edge cases, and make thoughtful tradeoffs.

• You're hands-on and enjoy prototyping, experimenting with new tools, and finding ways to bring ideas to life quickly.

• Strong analytical skills and experience using data to inform product decisions and measure results.

• Excellent communication skills and the ability to work closely with technical teams, customers, and company leadership.

• Comfort operating in ambiguous, fast-moving environments where priorities evolve as you learn.

Even Better If You Have

• 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 an early employee at a high-growth startup.

• Experience with healthcare technology or other industries with complex operational workflows.

Why Flossy

You'll join at a stage where the products you build can have an immediate impact on customers and meaningfully shape the direction of the company.

We're a small team that values ownership, curiosity, and speed. We ship quickly, learn from real customer usage, and continuously improve what we've built.

You'll work closely with people who care deeply about product quality and are excited by the opportunity to solve problems that haven't been solved before.

If you enjoy getting close to customers, experimenting with emerging AI capabilities, and taking ambitious ideas into production, we'd love to meet you.