Senior Product Manager; Miami

Senior Product Manager (Miami)

Reporting to: Head of Product

Location: Miami, FL - in‑office 4 days per week

Compensation: $120,000 – $150,000

This is not your typical job description. My name is Ari, founder of Extenteam. I entered the short‑term rental industry by mistake while studying Industrial Engineering at USC back in 2009. After running short‑term rental management companies for more than a decade, I started Extenteam — a staffing and proptech company that helps short‑term rental operators. We grew to a team of 350 people and more than $10MM ARR, but we also became complacent.

We focused on the wrong things and instead of executing, we spent too much time strategizing. Everything changed at our South of France offsite in October 2025. We decided that the future of the short‑term rental industry will be shaped by AI and automation. This is where Tailwind comes in.

Tailwind is the Extenteam automation and guest communication platform built specifically for the short‑term rental industry. It helps property management companies streamline operations by centralizing guest messaging, automating repeatable tasks, and improving response times across all communication channels. Our mission is to help our existing client base of 300 property management companies become more efficient using the Tailwind platform.

We are not building a better interface. We are building a platform where AI handles the work. If you turn ambiguous problems into clear specs, ship constantly, and always ask how a workflow can be replaced by an AI model before adding human complexity — we want to speak with you.

You will be the first Senior PM hired under our incoming Head of Product, owning one of two core product scopes: either our internal agent/shared‑services platform (the operational backbone powering our 20‑person customer service team), or our external SaaS platform (the product we are taking directly to STR property managers at scale). Exact scope will be defined in partnership with the Head of Product based on your background and where you can add the most leverage.

Either way, you will have meaningful ownership from day one. A core part of this role is owning the AI layer. You will work directly with engineering to define how AI models are prompted, evaluated, and improved over time. You will understand when a model is underperforming, why, and what needs to change — whether that is the prompt, the training data, the workflow design, or the human‑in‑the‑loop handoff.

• Own your product scope end‑to‑end: discovery, definition, prioritization, delivery, and iteration
• Write clear, unambiguous specs and user stories that engineers can act on without constant clarification
• Run structured discovery: talk to customers and internal agents, synthesize insights, identify patterns
• Maintain and groom a prioritized backlog, balancing quick wins with meaningful product bets
• Partner closely with engineering to scope work, manage tradeoffs, and keep delivery on track
• Own the performance and iteration of AI models within your product scope — define evaluation criteria, monitor output quality, and drive continuous improvement
• Lead automation‑first thinking in your area — every workflow you touch should ask whether a human is still needed, or whether AI can own it end‑to‑end
• Communicate progress, blockers, and decisions clearly to the Head of Product and leadership
• Track adoption and outcomes; use data to inform what to build next

• 3‑6 years of product management experience at a B2B SaaS company
• Hands‑on experience managing or iterating on AI models in a product context — you understand prompt design, evaluation frameworks, and how to improve model performance over time
• Strong spec‑writing and communication skills — you can turn fuzzy ideas into clear requirements
• Comfortable working in a fast‑moving, relatively unstructured environment
• Experience shipping full product features from discovery to launch
• Proven ability to work cross‑functionally with engineering, ops, and customer‑facing teams
• Hands‑on experience designing or improving workflows, decision trees, or automation‑ready…