Headquarters: United States

URL: http://www.pacaso.com

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 IC to architect that system and own its outcome. You'll define the reference architecture: how we recognize a customer across channels, what we know about them, how the system decides what to do next, and which of those decisions AI agents can make without a person. You'll prove the design with working prototypes you build yourself with AI tooling, then lead Engineering and Data in taking it to production.

This isn't a roadmap-and-backlog PM role, and it isn't a full-time production engineering role. It sits between them. You'll make product calls with Sales, Marketing, and leadership, make architecture calls with senior engineers, and be accountable for both.

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 architecture of the customer system. 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 write the architecture and the decisions behind it, and other teams build against it.

• The customer intelligence layer. Identity across channels, the event and signal model, 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. Evaluation frameworks, guardrails, observability, cost and latency budgets, and kill switches, in place before anything reaches a customer.

• The path to autonomy. What the system decides on its own, what still needs a person, and the evidence we need before we take that person out of the loop.

• Technical direction across teams. Build-versus-buy calls, data contracts with Engineering and Data, and integration standards for the CRM, messaging, email, and the site.

• The outcome. Funnel velocity (time from first interest to high intent, and to purchase) and the measured lift in qualified actions and closed sales.

Two examples of the work:

• An AI agent engages a new lead in the channel they prefer, qualifies them, and hands them to Sales at the right moment with the context Sales needs to close.

• A customer reads an email, chats with us, and comes back to the site a week later. They get one continuous experience, because the system remembers what we've already said and done.

Who you are

• Customer-obsessed. You start from the customer's experience, not the org chart or the backlog. When you have to choose between channels, surfaces, or features, the tiebreaker is what improves that experience. Our customers value clarity and discretion, and you design for both.

• An architect who still builds. You've designed systems other teams build on, and you still prototype yourself. You're expert at getting AI to do real work through prompting, tool use, and orchestration.

• Technically deep. You can read a data model, challenge an integration design, reason about latency, cost, and failure modes, and hold your own with senior engineers on how something should be built.

• Rigorous about autonomy. You design systems to run on their own, and you know how to prove they're ready. Evals and guardrails go in before launch, not after an incident.

• Accountable for outcomes. You measure yourself on results, not tasks shipped. You've stopped your own work when the impact wasn't there, and you can tell us about it.

• Fluent in business and technical. You can frame and defend a tradeoff with Sales, Marketing, and leadership, then go deep with engineers on the build. You own the decisi