Head of Sales

Who We Are
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.
 
Our Values:
F — Focus & Flow


Focus on what moves the needle. Remove noise. Build momentum instead of reacting to distractions.


Work should feel intentional, structured, and directed toward meaningful outcomes.


R — Real Work & Relationships


The work matters, and so do the people doing it.


We interact with respect, reliability, and direct communication.


Trust is built through consistent behavior, not personality.


E — Excellence Always


Excellence is disciplined craftsmanship. It isn’t perfectionism, but it is rigor.


Your work must be complete, thoughtful, and confidence-building.


E — Evolve Constantly


Adopt the Kaizen mindset: continuous improvement through small, daily upgrades.


We refine systems, raise standards, and learn faster than the challenges we face.


 
Mission
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)


Sales systems and process design


Team coaching and accountability


CRM integrity and pipeline visibility


Cross-functional alignment with Marketing, Product, and Coaching


This is a player-coach role: part strategist, part operator, part coach.
 
Responsibilities
Sales Performance & Pipeline Ownership


Own and improve core sales KPIs:



Booked Revenue


Call numbers and show-up rate


Call closes


Total pipeline value



Diagnose performance gaps across the funnel (lead quality, show rate, call quality, follow-up)


Identify and resolve bottlenecks impacting conversion and revenue


Establish forecasting discipline and pipeline visibility


Sales Process & Systems


Audit and redesign the full sales process:



Lead intake → qualification → setter → closer → follow-up → close



Improve segmentation between setters and closers to maximize efficiency and conversion


Standardize sales workflows, scripts, and best practices


Build repeatable systems for:



Lead routing and prioritization


Follow-up cadence and pipeline management


Call review and performance feedback



Own and optimize CRM (HubSpot):



Ensure accurate pipeline tracking and reporting


Improve adoption and usage across the team


Clean and maintain data integrity



Evaluate and implement sales enablement tools (call recording, analytics, etc.)


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 reps (reduce performance variance)


Support reps who are strong operators but lack formal sales training


Make recommendations on hiring, role design, and performance management


Call Quality & Conversion Improvement


Define what “great” looks like on a sales call


Improve:



Discovery quality


Objection handling


Offer alignment and positioning



Ensure ethical, high-integrity sales practices aligned with customer outcomes


Personally close deals (~10% capacity) to stay close to the process and model excellence


Marketing, Events & Product Alignment


Partner with Marketing to improve:



Lead quality


Application quality and scoring


Messaging alignment



Create clear handoffs between Marketing → Sales → Coaching


Collaborate on funnel optimization (top → middle → bottom)


Support event strategy:



Improve conversion from event attendees to customers


Align upsell pathways and follow-up



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:



Show rates


Close rates


Upsell rates



Maintain a culture of iteration and accountability within the sales team


 
Competencies
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 (not just blame reps)


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 (not just on the call)


 
Key Metrics
The Head of Sales is accountable for:


Total Booked Revenue


Flight School Sales Closes


Coaching Sales Closes


Strategy Sessions and Show Up Rates


 
Success in Role
(Suggested milestones; to be finalized with Mark during the first week)
First 30 Days :


Build full understanding of:



Sales funnel and segmentation (setters vs closers)


Current performance metrics and gaps


Team strengths and weaknesses



Begin CRM audit (HubSpot) and identify major issues


Start call reviews and initial coaching feedback


Identify top 2–3 leverage points impacting revenue


First 90 Days


Implement improvements to:



Sales process and workflows


CRM structure and reporting


Coaching and accountability systems



Improve consistency across reps


Establish clear KPI tracking and reporting cadence


Begin measurable improvements in show rate and/or close rate


6–12 Months


Build a reliable, predictable sales engine


Improve overall conversion rates and revenue per lead


Establish strong alignment with Marketing and Product


Reduce performance variance across the team


Create a scalable, system-driven sales organization


Success Profile
What experiences and skills would a successful Head of Sales likely bring to this role?


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


 
Compensation
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).