ABOUT EXTENTEAM

Extenteam is an AI-driven operations platform built for short-term rental property managers, automating guest communication and daily workflows with human-in-the-loop support across tens of thousands of properties.

Alongside our core STR business, we operate a multifamily property management division that generates $250,000 in monthly revenue, serving some of the largest operators in the country - companies running thousands of units across multiple states. The work is real, the clients are large, and the processes that power this division today are largely manual. We know what works. Now we want to build the technology layer that systematizes and automates it.

This role exists to lead that effort.

THE ROLE

This is the first product and engineering hire dedicated to the multifamily division. You will own the AI and automation layer for this side of the business - sitting at the intersection of product management and hands-on AI system design. You are not starting from scratch. There is $250K/month of revenue, real clients, real workflows, and real operational data to work with. Your job is to turn what works manually into a product that scales.

You will be working independently at the start - there is no dedicated engineering team from day one. You are expected to build, ship, and iterate on your own. If this work proves out, the function grows around you. That means you need to be genuinely technical: comfortable writing code, deploying pipelines, and owning the full stack of what you build.

You will design automation-first workflows, determine where AI can own a process end-to-end, and define where human oversight is still required. You will work closely with Extenteam agents and client-facing teams to surface workflow bottlenecks and translate operational reality into systems that actually work.

This role reports directly into the Head of Multifamily and is a founding position on the product and engineering function for this vertical.

WHAT YOU WILL OWN

• Own the AI and automation product scope for the platform: discovery, definition, prioritization, delivery, and iteration - largely independently at the start
• Write clear, unambiguous specs and documentation for the systems you build
• Run structured discovery with Extenteam agents and client-facing teams to surface workflow bottlenecks and automation opportunities
• Maintain a prioritized backlog, balancing quick wins with meaningful product bets
• Own the performance and iteration of AI models within your scope - define evaluation criteria, monitor output quality, and drive continuous improvement
• Build and maintain agentic workflows, Claude API pipelines, and MCP integrations directly - you are not just writing specs, you are shipping
• Lead automation-first thinking - 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 Multifamily and leadership
• Track adoption and outcomes; use data to inform what to build next

YOUR DAILY TOOLKIT

You should be comfortable and fast across all of these:

• Claude Code - this is your primary AI development interface; you live in it
• Claude API - pipelines, prompt chains, structured outputs, evaluation frameworks
• Terminal, CLI, bash - you are fluent at the command line
• GitHub - commits, branches, PRs, basic git hygiene
• Railway and/or AWS - you can deploy and manage what you build
• SQL and database connections - PostgreSQL, piping APIs into DBs, reading/writing data
• REST APIs - you can read docs and connect anything to anything
• MCP servers and tool-use integrations - you have built or extended them

WHO YOU ARE

Required

• 3-6 years of product management or builder experience, ideally at a B2B SaaS or proptech 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
• Deep familiarity with Claude Code - you use it as a force multiplier, not a crutch
• Proven ability to build agentic workflows, AI pipelines, or automation systems - you have shipped something real, solo or as a lead
• Strong written communication skills - you can turn fuzzy operational problems into clear system specs
• Comfortable working in a fast-moving, unstructured environment with no hand-holding
• Experience shipping full product features from discovery to launch, independently or with minimal support
• Hands-on experience designing or improving workflows, decision trees, or automation-ready processes
• Comfort working with data, dashboards, and analytics tools to guide decisions
• Must be based in or willing to relocate to Miami, Florida or Los Angeles, California

Preferred

• Experience in property management, proptech, or multifamily real estate
• Familiarity with property management platforms (Yardi, AppFolio, Buildium, Entrata, or similar)
• Background building or managing human-in-the-loop AI systems where model confidence determines when a human steps in
• Experience at a company going through a manual-to-AI or services-to-SaaS transition
• Familiarity with LLM orchestration tools or agentic workflow design beyond Claude
• Familiarity with ClickUp, Slack, or HubSpot - helpful but not required

KEY ATTRIBUTES

• Execution Focused: You move ideas into production quickly and consistently deliver measurable results
• AI-Native Builder: You do not bolt AI onto existing workflows - you design the workflow around what AI can own, define where humans add value, and write the code to make it real
• Domain-Curious: You take the time to understand this space deeply - the vocabulary, the pain points, the compliance requirements, and the people doing the work
• Systems Thinker: You understand how all parts of a product connect and design solutions that work at scale
• Technically Fluent: You ship code. You are not waiting for an engineering team to interpret your spec - you prototype, build pipelines, and deploy
• 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 the product, core agent and client workflows, and the operational processes currently running manually. First pipeline or automation scoped and in flight.
• 60 days: First automation shipped and running. Regular discovery cadence with agents and client-facing teams. AI model evaluation framework defined and in use. Clear ownership established.
• 90 days: Meaningful feature live. Visible product and AI momentum in your area. Model performance measurably improving. Data tracked and driving next priorities.

NOT A FIT IF

• You have only used Claude or ChatGPT through the UI
• You need an engineering team to execute your ideas
• You need detailed specs or close direction before you can start
• You are looking for a pure PM role with no hands-on building
• You are not prepared to be the first person in this function - with everything that comes with that

BENEFITS

• Health insurance
• Paid time-off