[Hiring] Head of Sales @The Land Geek

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.

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.

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.

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

• 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

• 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

• Skilled at giving direct, actionable feedback

• Able to raise the floor and ceiling of team performance

• Comfortable holding contractors accountable without traditional authority structures

• Experience working closely with Marketing and Product teams

• Ability to translate sales insights into actionable recommendations

• Strong communication and alignment skills

• Can balance short-term revenue needs with long-term scalability

• Identifies leverage points across the funnel (not just on the call)

The Head of Sales is accountable for:

1. Total Booked Revenue

2. Flight School Sales Closes

3. Coaching Sales Closes

4. Strategy Sessions and Show Up Rates

(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

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

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).