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).