Director of Lifecycle Marketing

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 this role exists

Pacaso created co-ownership of the second home: all the ownership a family actually uses, in the places they love, without the weight of owning it. The old way is whole ownership, with all of its cost and all of its operating burden for a few weeks of use a year. Moving a family from one to the other is among the most considered decisions they will ever make, and most of that consideration happens between conversations with Sales. Lifecycle marketing is how Pacaso shows up well in that time.

Three audiences make the case. Many people discover Pacaso years before they are ready to buy, and re-engaging them at the right moment is one of our largest growth levers. Active prospects deserve communication that matches the care of the decision they are weighing. And our Owners, the most credible proof the model works, should hear from us with the same taste as the homes they own. This is demand Pacaso has already earned. The job is to convert it.

IN BRIEF Own how Pacaso communicates with everyone in our database, from first inquiry through years of ownership.

What you'll own

You will shape lifecycle strategy with the VP of Marketing and build it yourself. Together you will decide how each of these audiences should experience Pacaso over time; you will then open Iterable and make it real. You are the most senior lifecycle practitioner at the company, reporting to the VP of Marketing and working closely with brand, creative, analytics and Sales.

Marketing at Pacaso runs lean and AI-native. We hire owners who multiply themselves with AI rather than teams that grow by headcount. You should already work this way, with AI drafting your variants, scoring your segments and checking your campaigns while your own judgment goes to strategy, taste and measurement.

REACTIVATION

Many buyers begin this journey long before they are ready. You will decide when and how to re-engage past inquiries, what would genuinely bring someone back and how a re-engaged buyer gets handed to Sales cleanly. It is the fastest path this role has to funded volume, and it is where you will start.

PROSPECT NURTURE

A Pacaso purchase can take months of consideration. You will design how a prospect experiences those months: what they hear after a first inquiry, how a specific home or market stays present in their thinking and what earns the consultation. Segmentation, personalization and disciplined testing are your instruments. Pacaso does not discount or rush its buyers, so the program earns attention through relevance rather than urgency.

OWNER COMMUNICATIONS

Owners are the heart of the brand and the source of our referrals and resales. Working with the owner experience team, you will define what Owners hear from Pacaso and when, from onboarding through arrival moments, home updates and referral programs, and set the governance that keeps those touches coordinated across teams. The standard is that every message an Owner receives feels like it came from the same hand that welcomed them home.

PLATFORM AND MEASUREMENT

You own the Iterable instance end to end: data architecture, deliverability, channel setup across email, SMS and push, and the connections to our CRM and data warehouse. You define lifecycle success in numbers (reactivation rate, conversion to consultation, owner engagement and revenue influenced) and report it to leadership monthly.

Who you are

You have led lifecycle for a considered, high-value purchase, in real estate, financial services, travel or something similar, and you never stopped building.

Specifically:

• 8+ years in lifecycle, CRM or retention marketing, with several of them owning the strategy.
• Journeys, segmentation, catalogs, templating and deliverability are muscle memory.
• AI-native in practice. You can point to programs where AI changed your speed or your results.
• Comfortable in SQL and fluent in funnel math, incrementality and holdout design.
• A writer's ear. You can draft a subject line that converts and catch a line that reads off voice for a brand built on restraint.
• Experienced working with Sales on lead scoring, handoff and pipeline reporting.

Compensation - $160,000 to $175,000 depending on experience and location plus equity

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

Pacaso is proud to be an equal opportunity employer. We welcome applicants of every race, religion, national origin, gender, sexual orientation, gender identity, gender expression, age, ability, and background — including veterans and individuals with disabilities. We believe a Crew as diverse as the owners we serve makes Pacaso stronger, and we're committed to building a workplace where every voice belongs.