Remotive
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Remote
Head of Sales
The Land Geek
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Worldwide
payments
$109k - $228k
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Contract
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2 weeks ago
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description Job Description
About The Land Geek:
At The Land Geek, we are dedicated to helping individuals achieve freedom through land investing. We provide a proven system for creating passive income, focusing on raw, undeveloped land. Our values are Focus & Flow, Real Work & Relationships, Excellence Always, and Evolve Constantly.
Role Overview:
The Head of Sales is responsible for building a predictable, scalable, and high-integrity sales function that consistently converts qualified leads into successful customers. This player-coach role owns sales performance, systems and process design, team coaching and accountability, CRM integrity, and cross-functional alignment with Marketing, Product, and Coaching.
Key Responsibilities:
Sales Performance & Pipeline Ownership:
Own and improve core sales KPIs including Booked Revenue, Call numbers and show-up rate, Call closes, and Total pipeline value. Diagnose performance gaps across the funnel, identify and resolve bottlenecks impacting conversion and revenue. Establish forecasting discipline and pipeline visibility.
Sales Process & Systems:
Audit and redesign the full sales process from lead intake to close and follow-up. Improve segmentation between setters and closers, standardize workflows, scripts, and best practices. Build repeatable systems for lead routing, follow-up cadence, and call review. Own and optimize CRM (HubSpot) for 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 to improve consistency and performance. Make recommendations on hiring, role design, and performance management.
Call Quality & Conversion Improvement:
Define standards for sales calls and improve discovery quality, objection handling, and offer positioning. Ensure ethical sales practices. Personally close deals to stay connected to the process.
Marketing, Events & Product Alignment:
Partner with Marketing to improve lead quality, messaging alignment, and funnel optimization. Support event strategy and align upsell pathways. Translate frontline sales insights into recommendations for Product and Coaching.
Data, Reporting & Continuous Improvement:
Build and maintain clear dashboards and reporting for leadership visibility. Identify trends and performance drivers using data. Run structured experiments to improve key rates. Maintain a culture of iteration and accountability within the sales team.
Qualifications:
Sales Leadership:
Proven ability to improve close rates and team performance. Experience managing setters/closers or multi-stage sales funnels. Strong coaching instincts, especially with non-traditional sales backgrounds.
Systems Thinking & Operational Rigor:
Ability to diagnose complex funnel issues. Experience building and refining sales processes in ambiguous environments. Comfort owning CRM systems and data quality.
Coaching & Performance Development:
Skilled at giving direct, actionable feedback. Able to raise the floor and ceiling of team performance. Comfortable holding contractors accountable without traditional authority structures.
Cross-Functional Collaboration:
Experience working closely with Marketing and Product teams. Ability to translate sales insights into actionable recommendations. Strong communication and alignment skills.
Strategic Thinking:
Can balance short-term revenue needs with long-term scalability. Identifies leverage points across the funnel.
Success Profile:
Experience in high-ticket sales (ideally info products, coaching, or education). Background in startup or fast-moving environments. Experience leading remote sales teams. Strong operator who can both build systems and execute within them. Comfortable working with imperfect data and building clarity over time.
Key Metrics:
Total Booked Revenue
Flight School Sales Closes
Coaching Sales Closes
Strategy Sessions and Show Up Rates
Success Milestones:
First 30 Days: Understand sales funnel, performance metrics, team dynamics. Begin CRM audit. Start call reviews. Identify top revenue leverage points.
First 90 Days: Implement improvements to sales process, CRM, coaching systems. Improve rep consistency. Establish KPI tracking. Begin measurable improvements in show rate and/or close rate.
6-12 Months: Build a reliable, predictable sales engine. Improve conversion rates and revenue per lead. Establish strong alignment with Marketing and Product. Reduce performance variance. Create a scalable, system-driven sales organization.
Compensation:
This is a 1099 contractor role offering a $9,000 monthly retainer and up to $120,000 in performance-based incentives, for a total annual compensation of up to $228,000.
At The Land Geek, we are dedicated to helping individuals achieve freedom through land investing. We provide a proven system for creating passive income, focusing on raw, undeveloped land. Our values are Focus & Flow, Real Work & Relationships, Excellence Always, and Evolve Constantly.
Role Overview:
The Head of Sales is responsible for building a predictable, scalable, and high-integrity sales function that consistently converts qualified leads into successful customers. This player-coach role owns sales performance, systems and process design, team coaching and accountability, CRM integrity, and cross-functional alignment with Marketing, Product, and Coaching.
Key Responsibilities:
Sales Performance & Pipeline Ownership:
Own and improve core sales KPIs including Booked Revenue, Call numbers and show-up rate, Call closes, and Total pipeline value. Diagnose performance gaps across the funnel, identify and resolve bottlenecks impacting conversion and revenue. Establish forecasting discipline and pipeline visibility.
Sales Process & Systems:
Audit and redesign the full sales process from lead intake to close and follow-up. Improve segmentation between setters and closers, standardize workflows, scripts, and best practices. Build repeatable systems for lead routing, follow-up cadence, and call review. Own and optimize CRM (HubSpot) for 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 to improve consistency and performance. Make recommendations on hiring, role design, and performance management.
Call Quality & Conversion Improvement:
Define standards for sales calls and improve discovery quality, objection handling, and offer positioning. Ensure ethical sales practices. Personally close deals to stay connected to the process.
Marketing, Events & Product Alignment:
Partner with Marketing to improve lead quality, messaging alignment, and funnel optimization. Support event strategy and align upsell pathways. Translate frontline sales insights into recommendations for Product and Coaching.
Data, Reporting & Continuous Improvement:
Build and maintain clear dashboards and reporting for leadership visibility. Identify trends and performance drivers using data. Run structured experiments to improve key rates. Maintain a culture of iteration and accountability within the sales team.
Qualifications:
Sales Leadership:
Proven ability to improve close rates and team performance. Experience managing setters/closers or multi-stage sales funnels. Strong coaching instincts, especially with non-traditional sales backgrounds.
Systems Thinking & Operational Rigor:
Ability to diagnose complex funnel issues. Experience building and refining sales processes in ambiguous environments. Comfort owning CRM systems and data quality.
Coaching & Performance Development:
Skilled at giving direct, actionable feedback. Able to raise the floor and ceiling of team performance. Comfortable holding contractors accountable without traditional authority structures.
Cross-Functional Collaboration:
Experience working closely with Marketing and Product teams. Ability to translate sales insights into actionable recommendations. Strong communication and alignment skills.
Strategic Thinking:
Can balance short-term revenue needs with long-term scalability. Identifies leverage points across the funnel.
Success Profile:
Experience in high-ticket sales (ideally info products, coaching, or education). Background in startup or fast-moving environments. Experience leading remote sales teams. Strong operator who can both build systems and execute within them. Comfortable working with imperfect data and building clarity over time.
Key Metrics:
Total Booked Revenue
Flight School Sales Closes
Coaching Sales Closes
Strategy Sessions and Show Up Rates
Success Milestones:
First 30 Days: Understand sales funnel, performance metrics, team dynamics. Begin CRM audit. Start call reviews. Identify top revenue leverage points.
First 90 Days: Implement improvements to sales process, CRM, coaching systems. Improve rep consistency. Establish KPI tracking. Begin measurable improvements in show rate and/or close rate.
6-12 Months: Build a reliable, predictable sales engine. Improve conversion rates and revenue per lead. Establish strong alignment with Marketing and Product. Reduce performance variance. Create a scalable, system-driven sales organization.
Compensation:
This is a 1099 contractor role offering a $9,000 monthly retainer and up to $120,000 in performance-based incentives, for a total annual compensation of up to $228,000.
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