Principal Technical Product Manager, AI Growth Systems

Pacaso , United States, Remote +1

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.

What you need

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.
A systems thinker who still builds. You think at the system level, and you still do the hands-on work: prototypes, UI design, and prompts. You're expert at getting AI to do real work through prompting, tool use, and orchestration.
Technically deep. You can read a data model, question an integration design, reason about latency, cost, and failure modes, and be a credible partner to senior engineers as they make design decisions.
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 product and system decisions, and you can follow and shape the technical ones.
A multiplier. You raise the bar for how Product, Engineering, and Data build with AI, through your designs, your reviews, and the patterns you leave behind.
A partner. Marketing and Sales are core stakeholders, and you'll co-own the buyer journey with our product owner for new-lead acquisition. When the path to impact runs through another team's area, you work with the owner to move it.
Fast at context. You go deep on systems you didn't build and turn a lot of information into a plan quickly.

What you'll bring

We'll ask for specific evidence of each of these. If you can't point to all six, this probably isn't the right fit yet.

Customer obsession. You take customer insights and translate them into real product features that deliver results.
A production agentic system. You've designed and shipped an autonomous or agentic system that runs end to end with minimal human intervention. You can show us what it decides on its own and how you knew it was making the right calls before you trusted it with real customers.
A measurable growth outcome. You've owned a growth, conversion, lifecycle, or re-engagement result. You can give us the baseline, what you changed, the lift, the time frame, and how you knew your work caused it.
Decisioning and intelligence layers. You've designed signals, identity, scoring, context, eligibility and caps, or next-best-action logic.
Prototype to production. You've built working prototypes yourself with AI tooling, beyond specs and slides, and taken at least one to production with engineers. You can tell us what you owned and what they owned.
Cross-team system design. You've owned the system-level design for a product that multiple teams built on or integrated with, and shaped the technical design with the engineers who owned it.

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)

Why You'll Love Working Here

We invest in our Crew the way we invest in our homes — thoughtfully, generously, and with care.

Competitive base salary and meaningful equity — every Crew member shares in what we're building
Discretionary time off – take the rest you need, when you need it
Premium medical, dental, and vision coverage for you and your family
Sponsored memberships to One Medical, Peloton, and WellHub for whole-person, modern healthcare
401(k) to help you build long-term security
Paid parental leave for primary and secondary caregivers
Home office stipend and a monthly internet and cell phone reimbursement to set you up for great remote work
Quarterly team gatherings and ongoing learning and development investment

Our Commitment

Principal Technical Product Manager, AI Growth Systems

The role

Principal Technical Product Manager, AI Growth Systems

The role

What you will do

Two examples of the work

What you need

Who you are

What you'll bring

Nice to have

This role isn't for you if

Pay and benefits

About Pacaso

About Pacaso

Why You'll Love Working Here

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Interview questions

Pacaso