Head of Sales

Head of Sales / Chief Revenue Officer (CRO)

A rapidly scaling, privately held real estate finance firm is seeking a Head of Sales / Chief Revenue Officer to architect and lead its next phase of growth. The company specializes in short-term lending solutions for real estate investors, including fix‑and‑flip and ground‑up construction financing. The business has experienced explosive expansion — growing from under $100M in annual originations just a few years ago to a projected $700M+ this year — and is now at a pivotal inflection point. To sustain this trajectory, the firm is investing in professionalizing its sales organization and building a repeatable, high‑performing origination engine.

This is a rare opportunity for a senior sales leader to build something meaningful from the ground up while stepping into a seat with real ownership, influence, and long‑term upside. Success in this role includes reducing reliance on individual relationships by building a scalable, team‑driven origination engine.

Role

The Head of Sales / CRO will be responsible for designing, building, and scaling a structured sales organization that drives predictable, profitable origination volume. This is not a “carry a bag” role — it is a sales leadership and organizational design mandate.

You will own hiring, training, performance management, sales process, and pipeline delivery, with full ownership of hiring decisions, performance management, and exiting underperformance to maintain high standards, while working closely with executive leadership and cross‑functional partners to ensure a best‑in‑class borrower experience.

This role requires a hands‑on leader who is willing to be deeply involved in hiring, onboarding, coaching, and process‑building alongside the team during the company’s next phase of growth.

What Success Looks Like

1. Build a High‑Performing Originations Team

• Recruit, hire, and onboard top‑tier sales originators
• Build and lead a team of 10+ quota‑carrying sales originators
• Define clear role expectations, compensation plans, and performance metrics
• Implement structured onboarding, training, and coaching programs
• Establish consistent performance management, accountability rhythms, and KPI tracking
• Translate market demand into repeatable sales processes and playbooks
• Implement data‑driven pipeline tracking, forecasting, and reporting
• Optimize CRM usage and sales analytics (HubSpot or comparable)
• Establish per‑originator production benchmarks, ramp expectations, and forecast accuracy standards
• Partner with underwriting and operations to improve speed, quality, and conversion

3. Build a Performance‑Driven, Service‑Led Sales Culture

• Define and embed sales values, standards, and behaviors
• Lead with high expectations, clarity, and transparency
• Coach teams to sell value and partnership — not price
• Build a culture of accountability, work ethic, and customer‑first service

Must‑Have Experience

• Proven success building and scaling sales teams of 10+ quota‑carrying reps from the ground up
• Strong track record hiring, training, coaching, and holding teams accountable to measurable outcomes
• Experience implementing CRM systems and managing through KPIs
• Comfortable operating in entrepreneurial, high‑growth organizations with limited existing structure
• Willingness to make hard decisions, including performance management and exits, to uphold standards

Preferred Backgrounds

• PropTech or investor‑focused financial platforms
• Commercial or residential investment sales
• Alternative lending or specialty finance