Principal Technical Product Manager, AI Growth Systems

About Pacaso Pacaso exists to enrich lives by making second home ownership possible and enjoyable for more people. We've reimagined the second home category — pairing a thoughtfully designed co-ownership model with simplified financials, equitable scheduling, and dedicated local property management, so owners get the joy of a true second home without the hassle. Since launch, Pacaso has facilitated more than $1. 2 billion in gross real estate transactions and service fees across 40+ destinations in the U. S. , Mexico, and Europe — including Aspen, Lake Tahoe, Napa, Malibu, Palm Springs, Cabo, Paris, London, and most recently Florence, Milan, and Rome. We've raised over $300 million in cumulative equity funding , closed the largest real estate Regulation A+ offering of 2025, and reserved the Nasdaq ticker PCSO as we build toward a public listing. Our work has been featured in The New York Times , The Wall Street Journal , Fortune , Forbes , CNBC , Bloomberg , and others. Recognition We're a Certified Great Place to Work and have been honored for both our culture and our category-defining work: - No. 5, Forbes America's Best Startup Employers (2026) — our second consecutive Top 10 ranking - Newsweek's America's Greatest Startup Workplaces (2025) - Winner, 2025 Inman Best of Proptech Awards — Consumer Experience & Marketplace Innovation - Fortune & Great Place To Work Best Workplaces in Real Estate (2024) - Best Workplace in the Bay Area™ (2023) - LinkedIn Top Startup (2022) · Glassdoor Best Places to Work, #6 (2022) The role Pacaso buyers are high-net-worth individuals making a considered purchase over months, sometimes years. They move between our site, email, messaging, and our Sales team, and today each of those runs on its own tools with its own picture of the customer. We believe one personalized system that follows each customer from first interest to purchase, and keeps serving them as an owner, will shorten the path to purchase and make our growth product-led. We're hiring a principal-level technical product manager to own that system and its outcome. You'll own the system-level design: the components, how they fit together, what the system decides and why, and how the AI agents behave. You'll own the roadmap, and you'll do hands-on work yourself: working prototypes built with AI tooling, UI design, and the prompts behind the agents. Engineering owns the technical design and implementation, and you shape and review it with them as it goes to production.

This is a technical product leadership role, not a backlog-management role and not a production engineering role. You'll make product calls with Sales, Marketing, and leadership, work through system tradeoffs with senior engineers, and be accountable for the outcome. Some of this is already moving. AI agents talk to our customers today, and parts of the data and decisioning exist. None of it runs end to end on its own yet. You'll take what's there, decide what to keep, and design the system that can. What you'll own - The system-level design. One design for new leads, dormant leads, and stalled buyers first, then owners who add a share, so the same person is served by one system instead of separate tools for each stage. You own the components, how they fit together, what the system decides and why, and the agent behavior and prompts. Engineering owns the technical design and implementation, and you shape and review it with them. - The customer intelligence layer. What the system knows about each customer across channels and how it acts on it: signals, shared memory and context, scoring, eligibility and frequency caps, and the next-best-action logic that decides what happens next. - Agent and workflow design. Which agents exist, what each one is allowed to decide, how they hand off to each other and to Sales, and the prompts, tools, and orchestration behind them. - Trust and reliability.