[Hiring] Director, Sales @Pacaso

Role Description

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
• 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.

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
• 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

Requirements

• 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
• Lead onboarding and ongoing enablement for Regional Directors
• Partner with the VP, Sales and People & Talent team on hiring, performance management, and succession planning
• Own the weekly and monthly sales cadence — pipeline reviews, forecast calls, deal inspection, and one-on-ones
• Deliver accurate weekly forecasts to the VP, Sales
• Translate the VP's sales strategy into clear team-level plans, quotas, and priorities
• Monitor KPIs and run targeted interventions when metrics slip
• Maintain a deep working knowledge of current market inventory and buyer dynamics
• Partner closely with Regional Managers to ensure a seamless lead handoff to Regional Directors
• Serve as the closing team's primary customer for Sales Enablement
• Build a tight feedback loop with the Acquisitions team
• Partner with Marketing on lead quality and top-of-funnel performance
• Represent the field's voice in cross-functional forums
• Drive integration of AI into the closing team's daily workflow
• Partner with Sales Enablement to operationalize AI within Salesforce

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