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Pacaso is an organization that helps people buy and own a second home through a property-specific LLC, as well as reduce the cost and hassle of ownership to make second-home owners
Director, Sales
Location
United States
Posted
32 days ago
Salary
0
Seniority
Lead
Job Description
Director, Sales
Pacaso
• 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. • 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. • 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. • 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.
Job Requirements
- 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.
Benefits
- 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.
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