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Head of Sales

The Land Geek

Worldwide Contract Remote $109 - 228 Posted 3 days ago

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Job Description

<div class="h3" dir="ltr" style="line-height: 1.2; margin-top: 0pt; margin-bottom: 0pt;">Who We Are</div>
 At The Land Geek, we’re all about helping people ditch the rat race and build real freedom through land investing. We’re passionate about teaching others how to create passive income using a simple, repeatable system that’s been tested and proven by thousands of land investors. No tenants, no toilets, no termites—just raw, undeveloped land and a whole lot of opportunity. Whether someone’s looking for a side hustle or a complete lifestyle overhaul, we’re here to show them what’s possible and cheer them on every step of the way.
 
<div class="h3" dir="ltr" style="line-height: 1.2; margin-top: 0pt; margin-bottom: 0pt;">Our Values:</div>
F — Focus & Flow
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Focus on what moves the needle. Remove noise. Build momentum instead of reacting to distractions.
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Work should feel intentional, structured, and directed toward meaningful outcomes.
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R — Real Work & Relationships
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The work matters, and so do the people doing it.
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We interact with respect, reliability, and direct communication.
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Trust is built through consistent behavior, not personality.
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E — Excellence Always
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Excellence is disciplined craftsmanship. It isn’t perfectionism, but it is rigor.
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Your work must be complete, thoughtful, and confidence-building.
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E — Evolve Constantly
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Adopt the Kaizen mindset: continuous improvement through small, daily upgrades.
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We refine systems, raise standards, and learn faster than the challenges we face.
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<div class="h3" dir="ltr" style="line-height: 1.2; margin-top: 12pt; margin-bottom: 12pt;">Mission</div>
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 role owns:
Sales performance (close rate, show rate, booked revenue)
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Sales systems and process design
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Team coaching and accountability
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CRM integrity and pipeline visibility
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Cross-functional alignment with Marketing, Product, and Coaching
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This is a player-coach role: part strategist, part operator, part coach.
 
<div class="h3" dir="ltr" style="line-height: 1.2; margin-top: 12pt; margin-bottom: 12pt;">Responsibilities</div>
Sales Performance & Pipeline Ownership
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Own and improve core sales KPIs:
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Booked Revenue
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Call numbers and show-up rate
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Call closes
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Total pipeline value
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Diagnose performance gaps across the funnel (lead quality, show rate, call quality, follow-up)
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Identify and resolve bottlenecks impacting conversion and revenue
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Establish forecasting discipline and pipeline visibility
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Sales Process & Systems
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Audit and redesign the full sales process:
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Lead intake → qualification → setter → closer → follow-up → close
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Improve segmentation between setters and closers to maximize efficiency and conversion
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Standardize sales workflows, scripts, and best practices
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Build repeatable systems for:
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Lead routing and prioritization
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Follow-up cadence and pipeline management
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Call review and performance feedback
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Own and optimize CRM (HubSpot):
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Ensure accurate pipeline tracking and reporting
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Improve adoption and usage across the team
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Clean and maintain data integrity
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Evaluate and implement sales enablement tools (call recording, analytics, etc.)
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Team Leadership & Coaching
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Lead, coach, and develop a team of sales contractors (setters and closers)
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Establish clear performance expectations and accountability systems
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Implement regular call reviews and feedback loops
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Improve consistency across reps (reduce performance variance)
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Support reps who are strong operators but lack formal sales training
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Make recommendations on hiring, role design, and performance management
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Call Quality & Conversion Improvement
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Define what “great” looks like on a sales call
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Improve:
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Discovery quality
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Objection handling
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Offer alignment and positioning
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Ensure ethical, high-integrity sales practices aligned with customer outcomes
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Personally close deals (~10% capacity) to stay close to the process and model excellence
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Marketing, Events & Product Alignment
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Partner with Marketing to improve:
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Lead quality
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Application quality and scoring
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Messaging alignment
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Create clear handoffs between Marketing → Sales → Coaching
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Collaborate on funnel optimization (top → middle → bottom)
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Support event strategy:
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Improve conversion from event attendees to customers
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Align upsell pathways and follow-up
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Translate frontline sales insights into recommendations for Product and Coaching
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Data, Reporting & Continuous Improvement
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Build and maintain clear dashboards and reporting for leadership visibility
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Identify trends and performance drivers using data
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Run structured experiments to improve:
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Show rates
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Close rates
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Upsell rates
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Maintain a culture of iteration and accountability within the sales team
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<div class="h3" dir="ltr" style="line-height: 1.2; margin-top: 12pt; margin-bottom: 12pt;">Competencies</div>
<div class="h3" dir="ltr" style="line-height: 1.38; margin-top: 14pt; margin-bottom: 4pt;">Sales Leadership</div>
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Proven ability to improve close rates and team performance
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Experience managing setters/closers or multi-stage sales funnels
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Strong coaching instincts, especially with non-traditional sales backgrounds
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<div class="h3" dir="ltr" style="line-height: 1.38; margin-top: 14pt; margin-bottom: 4pt;">Systems Thinking & Operational Rigor</div>
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Ability to diagnose complex funnel issues (not just blame reps)
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Experience building and refining sales processes in ambiguous environments
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Comfort owning CRM systems and data quality
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<div class="h3" dir="ltr" style="line-height: 1.38; margin-top: 14pt; margin-bottom: 4pt;">Coaching & Performance Development</div>
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Skilled at giving direct, actionable feedback
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Able to raise the floor and ceiling of team performance
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Comfortable holding contractors accountable without traditional authority structures
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<div class="h3" dir="ltr" style="line-height: 1.38; margin-top: 14pt; margin-bottom: 4pt;">Cross-Functional Collaboration</div>
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Experience working closely with Marketing and Product teams
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Ability to translate sales insights into actionable recommendations
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Strong communication and alignment skills
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<div class="h3" dir="ltr" style="line-height: 1.38; margin-top: 14pt; margin-bottom: 4pt;">Strategic Thinking</div>
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Can balance short-term revenue needs with long-term scalability
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Identifies leverage points across the funnel (not just on the call)
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<div class="h3" dir="ltr" style="line-height: 1.2; margin-top: 12pt; margin-bottom: 12pt;">Key Metrics</div>
The Head of Sales is accountable for:
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Total Booked Revenue
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Flight School Sales Closes
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Coaching Sales Closes
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Strategy Sessions and Show Up Rates
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<div class="h3" dir="ltr" style="line-height: 1.2; margin-top: 12pt; margin-bottom: 12pt;">Success in Role</div>
(Suggested milestones; to be finalized with Mark during the first week)
First 30 Days :
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Build full understanding of:
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Sales funnel and segmentation (setters vs closers)
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Current performance metrics and gaps
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Team strengths and weaknesses
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Begin CRM audit (HubSpot) and identify major issues
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Start call reviews and initial coaching feedback
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Identify top 2–3 leverage points impacting revenue
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First 90 Days
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Implement improvements to:
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Sales process and workflows
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CRM structure and reporting
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Coaching and accountability systems
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Improve consistency across reps
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Establish clear KPI tracking and reporting cadence
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Begin measurable improvements in show rate and/or close rate
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6–12 Months
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Build a reliable, predictable sales engine
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Improve overall conversion rates and revenue per lead
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Establish strong alignment with Marketing and Product
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Reduce performance variance across the team
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Create a scalable, system-driven sales organization
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<div class="h3" dir="ltr" style="line-height: 1.2; margin-top: 12pt; margin-bottom: 12pt;">Success Profile</div>
What experiences and skills would a successful Head of Sales likely bring to this role?
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Experience in high-ticket sales (ideally info products, coaching, or education)
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Background in startup or fast-moving environments
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Experience leading remote sales teams
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Strong operator who can both build systems and execute within them
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Comfortable working with imperfect data and building clarity over time
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<div class="h3" dir="ltr" style="line-height: 1.2; margin-top: 12pt; margin-bottom: 12pt;">Compensation</div>
This is a 1099 contractor role offering a $9,000 monthly retainer and up to $120,000 in performance-based incentives (up to $228,000 total annual compensation). 
 
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