Head of Sales

Location: New York, NY
Work Model: Hybrid (4 days in-office)
Industry: SaaS / AI-powered Commercial Real Estate Technology
Compensation: $200,000 base / ~$350,000 OTE + 0.5–1% equity

About the Company

We are a fast-growing, venture-backed SaaS company building AI-driven solutions that are transforming the commercial real estate industry. Backed by leading investors, we have raised over $100M to date and achieved 10x revenue growth in the past year. Currently approaching $5M ARR with projections to more than double next year, we are scaling quickly and investing in top talent to drive the next phase of growth. Our culture is product-obsessed, customer-focused, and highly collaborative, with a flat structure where every team member has an outsized impact.

The Opportunity

We are seeking a Head of Sales (VP-level) to build and lead our go-to-market function. This is an executive-level role with direct ownership of revenue and sales strategy, reporting to the CEO. The ideal candidate is a hands-on leader who is equally comfortable coaching a small team of AEs and SDRs, diving into complex enterprise deals, and collaborating with product and marketing to refine messaging and strategy.

This is a unique opportunity to join a high-growth startup at a pivotal stage, helping us scale from $5M to $12M+ ARR while laying the foundation for a world-class sales organization.

Responsibilities

• Own revenue strategy and execution across all sales channels
• Hire, manage, and scale a growing sales team (currently 2 AEs + 1 SDR, with aggressive hiring plans)
• Actively participate in key deals: join calls, coach reps, and serve as executive sponsor for strategic opportunities
• Develop and implement sales playbooks, processes, quotas, and forecasts
• Provide structured coaching and training to drive consistent performance and attainment
• Partner cross-functionally with product and marketing on messaging, positioning, and go-to-market experiments
• Establish metrics, dashboards, and reporting to provide visibility into pipeline, forecasting, and performance

Requirements

• Proven success in SaaS sales leadership roles, with experience scaling revenue past $10M ARR
• Hands-on approach: comfortable diving into deals, coaching directly from call reviews, and setting the tone for the team
• Track record of hiring, developing, and retaining high-performing sales talent
• Strong background in complex, enterprise-level sales cycles with multiple stakeholders
• Analytical and strategic mindset, with the ability to forecast accurately and make data-driven decisions
• Entrepreneurial spirit—experience as a founding AE, early-stage leader, or startup operator preferred
• Based in or willing to relocate to New York City; ability to work in-office 4 days per week
• Willingness to travel as needed for customer engagement