Senior Product Manager (Miami)

Reporting to: Head of Product

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

Compensation: $120,000 – $150,000

About the Role

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.

The Role

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.

What You Will Own

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

Who You Are

Required

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 processes
Comfort working with data, dashboards, and analytics tools to guide decisions
Proficient in Jira — you use it daily to manage your backlog, write and organize tickets, track sprint progress, and keep engineering aligned without constant back and forth
Must be based in or willing to relocate to Miami, Florida

Preferred

Experience building or managing human‑in‑the‑loop AI systems where model confidence determines when a human steps in
Background in proptech, hospitality tech, or adjacent industries
Experience at a company going through a services‑to‑SaaS or manual‑to‑AI transition
Familiarity with LLM‑based products, AI orchestration tools, or agentic workflow design

Key Attributes

Execution Focused: You move ideas into production quickly and consistently deliver measurable results
AI‑Native Thinker: You do not bolt AI onto existing workflows — you design the workflow around what AI can own, and define where humans add value that models cannot replicate yet
Systems Thinker: You understand how all parts of a product connect and design solutions that work at scale
Technically Fluent: You understand how systems integrate and can work directly with engineering teams
High Velocity: You thrive in fast‑paced environments, iterate quickly, and maintain momentum without sacrificing quality
Ambiguity Crusher: You bring clarity to messy, unclear situations and create order that others can follow

What Success Looks Like

30 days

Deep understanding of your assigned product scope, engineering team, core user workflows, and the AI models currently in production
Spec process running and backlog clean

60 days

First features scoped and in flight
Regular discovery cadence with customers or internal agents
AI model evaluation framework defined and in use
Clear ownership established

90 days

Meaningful feature shipped
Visible product momentum in your area
AI model performance measurably improving
Data tracked and driving next priorities

Why Join Extenteam

Real ownership from day one: Not a feature‑factory environment — you will have genuine scope and accountability over both product and AI model performance
Strong engineering team: Work alongside experienced engineers who have collaborated across multiple projects worldwide and hold a high standard for their work
Executive visibility: Direct access to the Head of Product and leadership with fast feedback loops
Competitive compensation: $120,000‑$150,000 base

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