About Us
The Land Geek empowers individuals to achieve financial independence through strategic land investing. We are dedicated to equipping others with a proven, straightforward system for generating passive income, a method adopted successfully by thousands of land investors. Our focus is on the untapped potential of undeveloped land, offering a unique opportunity for those seeking supplementary income or a complete career shift. We are committed to guiding and supporting our community every step of the way.
Our Guiding Principles:
F — Focus & Flow
- Prioritize high-impact activities, minimize distractions, and cultivate consistent momentum.
- Ensure work is purposeful, structured, and directed towards achieving significant goals.
R — Real Work & Relationships
- Value the importance of meaningful contributions and the individuals who make them.
- Foster interactions built on respect, dependability, and transparent communication.
- Cultivate trust through consistent actions and reliability.
E — Excellence Always
- Embrace disciplined execution and meticulous craftsmanship in all endeavors.
- Deliver work that is comprehensive, insightful, and inspires confidence.
E — Evolve Constantly
- Adopt a philosophy of continuous improvement through incremental daily advancements.
- Refine processes, elevate standards, and learn proactively to overcome evolving challenges.
Role Overview
The Head of Sales will be instrumental in developing a dependable, scalable, and ethical sales operation that effectively converts qualified prospects into satisfied clients. This pivotal role encompasses responsibility for:
- Sales performance metrics (e.g., conversion rates, attendance rates, revenue secured)
- Designing and implementing robust sales systems and processes
- Mentoring and ensuring accountability within the sales team
- Maintaining CRM accuracy and clear pipeline visibility
- Fostering collaboration with Marketing, Product, and Coaching departments
This position demands a player-coach approach, integrating strategic vision, hands-on operational execution, and effective team development.
Key Responsibilities
Sales Performance & Pipeline Management
- Oversee and enhance critical sales Key Performance Indicators (KPIs), including:
- Call Volume and Attendance Rates
- Analyze performance data to identify and address gaps across the sales funnel, from lead qualification to call quality and follow-up effectiveness.
- Proactively resolve bottlenecks that impede conversion rates and revenue generation.
- Establish rigorous forecasting practices and ensure transparent pipeline visibility.
Sales Process & System Optimization
- Conduct comprehensive audits and redesign the end-to-end sales process, encompassing:
- Lead intake through qualification, handover to setters, closing, and post-sale follow-up.
- Enhance the segmentation between sales development representatives (setters) and closers to maximize efficiency and conversion.
- Standardize sales workflows, scripts, and best practices for consistent execution.
- Develop and implement repeatable systems for:
- Efficient lead routing and prioritization.
- Effective follow-up cadences and pipeline management.
- Structured call reviews and performance feedback mechanisms.
- Manage and optimize the CRM system (HubSpot), ensuring:
- Accurate pipeline tracking and reporting.
- High adoption and utilization rates by the team.
- Data integrity and cleanliness.
- Evaluate and integrate sales enablement tools, such as call recording and analytics platforms.
Team Leadership & Coaching
- Lead, mentor, and develop a team of contract sales professionals (setters and closers).
- Define clear performance expectations and implement robust accountability frameworks.
- Facilitate regular call reviews and provide constructive feedback to enhance performance.
- Drive consistency in performance across all sales representatives, minimizing individual variance.
- Support team members who excel operationally but may lack formal sales training.
- Provide recommendations regarding hiring, role structuring, and performance management strategies.
Call Quality & Conversion Enhancement
- Define the benchmark for exceptional performance on sales calls.
- Improve key areas of sales interaction, including:
- Quality of discovery conversations.
- Effectiveness in handling objections.
- Alignment and positioning of offers.
- Ensure all sales practices are ethical and prioritize positive customer outcomes.
- Dedicate approximately 10% of capacity to personally closing deals, maintaining direct engagement with the sales process and modeling best practices.
Marketing, Events & Product Alignment
- Collaborate with the Marketing team to enhance:
- Lead quality and qualification standards.
- Application quality and scoring mechanisms.
- Messaging consistency across all touchpoints.
- Establish seamless handoffs between Marketing, Sales, and Coaching functions.
- Contribute to the optimization of the entire sales funnel, from top to bottom.
- Support event strategy by:
- Improving conversion rates from event attendees to customers.
- Aligning upsell pathways and follow-up procedures.
- Translate frontline sales insights into actionable recommendations for Product and Coaching development.
Data, Reporting & Continuous Improvement
- Develop and maintain comprehensive dashboards and reports for leadership visibility.
- Analyze data to identify performance trends and key drivers.
- Execute structured experiments to drive improvements in:
- Foster a culture of iteration and accountability within the sales team.
Required Competencies
Sales Leadership
- Demonstrated success in improving close rates and overall team performance.
- Experience managing setters, closers, or multi-stage sales funnels.
- Strong aptitude for coaching, particularly with individuals from diverse sales backgrounds.
Systems Thinking & Operational Rigor
- Ability to thoroughly diagnose complex funnel challenges beyond individual rep performance.
- Experience in building and refining sales processes within evolving and often ambiguous environments.
- Proficiency and comfort in managing CRM systems and ensuring data accuracy.
Coaching & Performance Development
- Skill in delivering direct, actionable, and constructive feedback.
- Capability to elevate both the baseline and peak performance of the team.
- Comfort in holding contractors accountable, even without formal hierarchical authority.
Cross-Functional Collaboration
- Proven track record of working effectively with Marketing and Product teams.
- Ability to translate sales observations into valuable, actionable insights for other departments.
- Excellent communication and alignment-building skills.
Strategic Thinking
- Capacity to balance immediate revenue objectives with long-term scalability goals.
- Skill in identifying strategic leverage points throughout the sales process, not just during direct customer interactions.
Key Performance Metrics
The Head of Sales will be accountable for achieving the following outcomes:
- Total Booked Revenue
- Flight School Sales Closes
- Coaching Sales Closes
- Strategy Session Attendance Rates
Role Success Milestones
(Tentative targets, to be finalized with Mark within the initial week)
First 30 Days:
- Develop a comprehensive understanding of:
- The sales funnel and its segmentation (setters vs. closers).
- Current performance metrics, identifying key gaps.
- The strengths and development areas of the team.
- Initiate an audit of the CRM (HubSpot) and pinpoint significant areas for improvement.
- Commence call reviews and deliver initial coaching feedback.
- Identify the top 2-3 critical leverage points impacting revenue.
First 90 Days:
- Implement enhancements to:
- Sales processes and workflows.
- CRM structure and reporting capabilities.
- Coaching and accountability systems.
- Achieve greater consistency in performance across all sales representatives.
- Establish clear KPI tracking mechanisms and a regular reporting cadence.
- Demonstrate measurable improvements in either show-up rates or close rates.
6–12 Months:
- Establish a robust, predictable, and scalable sales engine.
- Improve overall conversion rates and revenue generated per lead.
- Cultivate strong alignment and collaboration with Marketing and Product departments.
- Significantly reduce performance variability across the sales team.
- Build a sales organization that is system-driven and scalable.
Ideal Candidate Profile
What experiences and skills would a successful Head of Sales likely possess for this role?
- Experience in high-ticket sales environments, particularly with information products, coaching, or educational programs.
- Background in startup or fast-paced, dynamic settings.
- Experience leading remote sales teams effectively.
- A strong operational mindset combined with the ability to design systems and execute within them.
- Comfort working with incomplete data and a proven ability to bring clarity over time.
Compensation Details
This is a 1099 contractor position offering a base monthly retainer of $9,000, with the potential for up to $120,000 in performance-based incentives, resulting in a total annual compensation package of up to $228,000.