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Director, Sales

Remote, United States

About Pacaso:
Pacaso exists to enrich lives by making second home ownership possible and enjoyable for more people. Our innovative co-ownership model is the easiest, smartest and most responsible way for people to experience the joy of a second home. We provide all the benefits of true ownership without the hassles through our simplified financial structure, easy and equitable scheduling, and dedicated local property management.Founded by former Zillow executives, Pacaso has facilitated over $1 billion in gross real estate transactions and service fees across more than 40 markets nationwide, as well as internationally in Paris, London, and Cabo.

We have been featured in The New York Times, Wall Street Journal, Fortune, Forbes, CNBC and more.Pacaso is a certified Great Place to Work and has received numerous accolades for its workplace culture. Fortune and Great Place To Work named Pacaso to the 2024 Best Workplaces in Real Estate list. In 2023, Pacaso was recognized as a Best Workplace in the Bay Area™, and in 2022, it ranked among the Best Medium Workplaces™, Best Workplaces for Real Estate™, and Best Workplaces for Millennials™. Additionally, Pacaso was ranked #6 on Glassdoor's 2022 list of Best Places to Work and was one of LinkedIn's top startups in 2022.

About the Role:
The Director, Sales leads Pacaso's Regional Directors — the closers who convert prospective buyers into homeowners across our markets. Reporting to the VP, Sales, this role owns the day-to-day performance of the closing team: hitting revenue targets, coaching Regional Directors to consistently exceed quota, maintaining pipeline rigor, and translating strategy from the Senior Leadership Team into disciplined field execution. The Director, Sales is a player-coach who runs the weekly cadence of the business, spots performance issues early, and partners closely with the Regional Manager Team, Sales Enablement, and cross-functional leaders to keep the team firing.

Job Responsibilities:

Team Leadership & Development

  • Directly manage and develop a team of Regional Directors across multiple markets, driving consistent achievement of individuals
  • Coach Regional Directors on tour execution, discovery, objection handling, and closing techniques; ride along on virtual and on-site tours to diagnose performance and elevate craft
  • Lead onboarding and ongoing enablement for Regional Directors, including ramp plans for new hires, market-specific inventory training, and sales skill development
  • Partner with the VP, Sales and People & Talent team on hiring, performance management, and succession planning for the closing team; own the bar for who joins and who grows
  • Foster an inclusive, high-performance culture where Regional Directors feel supported, challenged, and proud to carry the Pacaso mission

Sales Performance & Execution

  • Own the weekly and monthly sales cadence — pipeline reviews, forecast calls, deal inspection, and one-on-ones — to ensure disciplined execution across the closing team
  • Deliver accurate weekly forecasts to the VP, Sales, identifying risks and upside early and holding Regional Directors accountable for forecast accuracy and data hygiene
  • Translate the VP's sales strategy into clear team-level plans, quotas, and priorities, and ensure the team understands how their work ladders up to company goals
  • Monitor KPIs (list KPI’s) and run targeted interventions — training, process changes, territory adjustments — when metrics slip
  • Maintain a deep working knowledge of current market inventory and buyer dynamics so you can coach credibly and step into deals when needed



Cross-Functional Partnership

  • Partner closely with Regional Managers to ensure a seamless lead handoff to Regional Directors — align on lead qualification criteria, handoff SLAs, context completeness, and shared conversion metrics; run joint pipeline reviews to tighten the top-of-funnel-to-close motion and surface friction early
  • Serve as the closing team's primary customer for Sales Enablement — co-create playbooks, onboarding curriculum, tour scripts, and market-specific training; provide structured field feedback on what's working and what the team needs next; champion adoption of new enablement programs and measure their impact on ramp time and win rates
  • Build a tight feedback loop with the Acquisitions team so the homes we source reflect real, near-term buyer demand — systematize how Regional Directors capture prospect preferences and surface specific properties or listings buyers are asking about; meet regularly with Acquisitions leadership to translate field intelligence into sourcing priorities and flag inventory gaps before they cost us deals
  • Partner with Marketing on lead quality and top-of-funnel performance, and with Operations on the buyer handoff and homeowner experience
  • Represent the field's voice in cross-functional forums — bringing buyer feedback, market intelligence, and operational friction to Product, Marketing, and Operations partners

AI & Technology Enablement

  • Drive integration of AI into the closing team's daily workflow — prospect research, buyer briefings, call and tour recaps, follow-up drafting, objection prep, and deal coaching — so Regional Directors spend more time in front of buyers and less time on prep and admin
  • Partner with Sales Enablement to operationalize AI within Salesforce — lead scoring, next-best-action prompts, automated activity capture, pipeline hygiene nudges, and AI-generated deal summaries — and hold the team accountable to using these tools to lift conversion and forecast quality

Travel: ~10 - 15% for market visits, team ride-alongs, and key deal support

Qualifications:

  • 7+ years of quota-carrying sales experience with a clear track record of personally exceeding targets in a consultative, high-consideration sale
  • 3+ years managing sales professionals or a multi-market team of sellers.
  • Proven ability to run a tight forecast and operational cadence — weekly pipeline discipline, deal inspection, and accurate multi-market rollups
  • Strong coaching instincts; demonstrated history of developing sellers into top performers and promoting from within
  • Background in real estate, luxury, prop-tech, or another high-ticket consumer sale strongly preferred
  • Experience working with high net worth individuals
  • Data-fluent — comfortable pulling insights from Salesforce (or equivalent) and using metrics to drive decisions, not just report them
  • Hands-on experience deploying AI tools within a sales organization — call/meeting intelligence platforms, AI writing assistants, and AI-enhanced Salesforce workflows — with a point of view on where AI creates leverage and where it doesn't
  • Excellent cross-functional communicator who can partner with Marketing, Ops, Product, Enablement, and Finance without friction
  • Mission-driven, culture-carrier, and comfortable in a fast-moving environment where markets and playbooks evolve quickly
  • Willingness to travel 10–15% of the time

You’ll love working at Pacaso because of our ...

  • Competitive salary and stock options.
  • Unlimited, flexible PTO for exempt employees.
  • Excellent medical, dental and vision insurance.
  • Sponsored memberships to One Medical, Ginger and Carrot.
  • 401(k) to help you save for the future.
  • Paid maternity and paternity leave.
  • Generous home office stipend and monthly cell phone reimbursement.
  • Quarterly remote team building events and L&D opportunities.

Pacaso encourages applications from people of all races, religions, national origins, genders, sexual orientations, gender identities, gender expressions and ages, as well as veterans and individuals with disabilities.     

 

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