Head of Sales
Prevail Recruiting
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.
The 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, while working closely with executive leadership and cross-functional partners to ensure a best-in-class borrower experience. What Success Looks Like 1. Build a High-Performing Originations Team- Recruit, hire, and onboard top-tier 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 and forecasting
- Optimize CRM usage and sales analytics (HubSpot or comparable)
- Partner with underwriting and operations to improve speed, quality, and conversion
- 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
- Proven success building and scaling sales teams in financial services, real estate finance, or similar high-velocity, relationship-driven environments
- Strong track record hiring, training, 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
- Real estate lending or private credit sales leadership
- PropTech or investor-focused financial platforms
- Commercial or residential investment sales
- Alternative lending or specialty finance
Vacancy posted 1 day ago
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