The Opportunity

Buildout is building the Broker Operating System for commercial real estate. You will own the strategy and roadmap for AI, the AI assistant embedded across the suite: the skills it performs, the judgment of when it should use AI reasoning versus the platform's own exact calculations, and the quality bar it ships against.

You will also bring AI into the marketing and document creation workflows that made Buildout the leader in commercial real estate, helping brokers build the materials that win and sell listings, so they get to market and pitch faster. You will work day to day with engineering and design.

How You'll Contribute at Buildout

Set the vision, strategy, and roadmap for AI: decide which skills we build, in what order, and why
Be customer facing: spend real time with customers, watch how they actually work, test AI skills against their live workflows, and carry what you learn directly into the roadmap and eval sets
Prioritize the backlog against broker value, technical feasibility, and quality risk, and run it from concept through launch and iteration
Define what "good enough" means: build and maintain the eval sets and quality bar each AI skill ships against, and review regressions before every release
Decide deterministic vs LLM per skill, knowing when a rule-based engine beats a model
Own prompt, context, and retrieval design and improve it against measured evaluations rather than gut feel
Set the guardrails: grounding in real records, permission-scoping, confirm-before-action, hallucination controls, and rollback plans for non-deterministic failures
Turn broker workflows into skill specs an engineer can build from: trigger, what it reads, what it writes, guardrail, surface
Ask sharp questions and unblock engineering
Measure dual metrics: product outcomes (adoption, task success) and model quality (accuracy, groundedness, regression rate). Watch latency and cost against quality

What Makes a Great Candidate

You get outside the building: regularly interview users, observe workflows, and validate assumptions before committing engineering time
You’re an AI pragmatist: excited by AI but disciplined enough to know when deterministic logic is the better answer
You’re a builder, not just a planner: using tools like Claude, Cursor, or Replit to prototype ideas and learn quickly
You want evidence, not opinions: defining success upfront and using customer feedback and data to guide product decisions
You’re comfortable in the gray: making thoughtful decisions despite ambiguity, tradeoffs, and rapidly evolving technology
You’re equally strategic and hands-on: connecting long-term product vision with tactical work that gets products shipped

You also have:

5+ years in product management, including 1–2 AI/ML or LLM-powered features shipped to real users
Hands-on experience with rapid prototyping tools (Claude, Cursor, Replit)
Comfort with prompt and context engineering, retrieval-augmented generation (RAG), plus a practical grasp of what LLMs can and cannot do
Strong product discovery skills: customer interviews, problem validation, and translating insights into roadmap priorities
Experience partnering closely with Engineering and Design to ship high-quality software in a fast-paced environment
Enough technical depth to trade off model, data, and latency with engineers
Clear communication to technical and non-technical audiences, and comfort with ambiguity and probabilistic outcomes

Bonus

CRE, proptech, or vertical SaaS experience
Experience building assistants, copilots, or agentic products

Role Details

Location: Fully remote role open across most of the US
Travel: Occasional travel for customer meetings, conferences, team offsites, or other business needs (a few times per year)
Compensation: $150,000–$170,000
Reporting To: George Mountis, SVP, Product

Perks & Benefits

Impactful insurance and benefit options, including 2 medical plans, 100% coverage of employee dental and vision premiums, HSA seed, company-paid STD, LTD, life insurance, telemedicine, and a $400/year wellness benefit
Flexible PTO, 14 paid company holidays, paid parental leave, and give back days
401(k) with 4% company match and immediate vesting
Fully remote work culture with $600/year remote work reimbursement and annual in-person company kickoff
Challenging problems to solve with a committed and supportive team invested in your growth
A quirky culture where you’re encouraged to bring your whole self to work

Senior Product Manager, AI