Head of Sales

Head of Sales - Remote

The Land Geek is seeking a passionate and experienced Head of Sales to build and lead a high-integrity sales function. We empower individuals to achieve financial freedom through land investing, offering a proven system with no tenants, toilets, or termites. If you're driven by helping others and building scalable sales operations, this remote role is for you.

About The Land Geek

At The Land Geek, we're dedicated to teaching people how to create passive income through land investing. We provide a simple, repeatable system that has been successfully used by thousands. Our mission is to guide individuals toward financial independence and a better lifestyle.

Our core values are:

• Focus & Flow: Prioritize impactful tasks and build momentum.
• Real Work & Relationships: Value meaningful work and respectful, reliable interactions.
• Excellence Always: Strive for rigorous, thoughtful, and confidence-building work.
• Evolve Constantly: Embrace continuous improvement and learn faster than challenges.

About the Role

The Head of Sales is responsible for developing a predictable, scalable, and ethical sales function that consistently converts qualified leads into successful customers. This is a player-coach role, requiring a blend of strategic thinking, operational execution, and team leadership.

This role owns:

• Sales performance (close rate, show rate, revenue growth)
• Sales systems and process design
• Team coaching and accountability
• CRM integrity and pipeline visibility
• Cross-functional alignment with Marketing, Product, and Coaching

Key Responsibilities

Sales Performance & Pipeline Ownership:

• Own and improve core sales Key Performance Indicators (KPIs) including Booked Revenue, Call Numbers, Show-Up Rate, Call Closes, and Total Pipeline Value.
• Diagnose performance gaps across the sales funnel and identify/resolve bottlenecks impacting conversion and revenue.
• Establish forecasting discipline and ensure pipeline visibility.

Sales Process & Systems:

• Audit and redesign the full sales process from lead intake to follow-up.
• Improve segmentation between setters and closers to maximize efficiency.
• Standardize sales workflows, scripts, and best practices.
• Build repeatable systems for lead routing, follow-up cadence, and pipeline management.
• Own and optimize the CRM (HubSpot), ensuring accurate tracking, reporting, and data integrity.
• Evaluate and implement sales enablement tools.

Team Leadership & Coaching:

• Lead, coach, and develop a team of sales contractors (setters and closers).
• Establish clear performance expectations and accountability systems.
• Implement regular call reviews and feedback loops.
• Improve consistency across sales representatives and support their development.
• Make recommendations on hiring, role design, and performance management.

Call Quality & Conversion Improvement:

• Define standards for effective sales calls and improve discovery, objection handling, and offer positioning.
• Ensure ethical, high-integrity sales practices aligned with customer outcomes.
• Personally close deals (approximately 10% capacity) to stay connected to the sales process.

Marketing, Events & Product Alignment:

• Partner with Marketing to improve lead quality, application scoring, and messaging alignment.
• Create clear handoffs between Marketing, Sales, and Coaching departments.
• Collaborate on funnel optimization and support event strategy to improve conversion rates.
• Translate frontline sales insights into actionable recommendations for Product and Coaching teams.

Data, Reporting & Continuous Improvement:

• Build and maintain clear dashboards and reports for leadership.
• Identify trends and performance drivers using data.
• Run structured experiments to improve show rates, close rates, and upsell rates.
• Foster a culture of iteration and accountability within the sales team.

Competencies

• Sales Leadership: Proven ability to improve close rates and team performance, experience managing multi-stage sales funnels, and strong coaching instincts.
• Systems Thinking & Operational Rigor: Ability to diagnose complex funnel issues, experience building and refining sales processes, and comfort with CRM systems and data quality.
• Coaching & Performance Development: Skilled at giving direct, actionable feedback and holding contractors accountable.
• Cross-Functional Collaboration: Experience working closely with Marketing and Product teams, strong communication skills.
• Strategic Thinking: Ability to balance short-term revenue needs with long-term scalability and identify leverage points across the entire funnel.

Compensation

This is a 1099 contractor role offering a $9,000 monthly retainer with up to $120,000 in performance-based incentives, for a total potential annual compensation of up to $228,000.