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).

Remote HubSpot Jobs in Canada

Head of Sales

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