Head of Sales

e 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 designTeam coaching and accountabilityCRM integrity and pipeline visibilityCross-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 RevenueCall numbers and show-up rateCall closesTotal pipeline valueDiagnose performance gaps across the funnel (lead quality, show rate, call quality, follow-up)Identify and resolve bottlenecks impacting conversion and revenueEstablish forecasting discipline and pipeline visibility Sales Process & Systems Audit and redesign the full sales process:Lead intake → qualification → setter → closer → follow-up → closeImprove segmentation between setters and closers to maximize efficiency and conversionStandardize sales workflows, scripts, and best practicesBuild repeatable systems for:Lead routing and prioritizationFollow-up cadence and pipeline managementCall review and performance feedbackOwn and optimize CRM (HubSpot):Ensure accurate pipeline tracking and reportingImprove adoption and usage across the teamClean and maintain data integrityEvaluate 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 systemsImplement regular call reviews and feedback loopsImprove consistency across reps (reduce performance variance)Support reps who are strong operators but lack formal sales trainingMake recommendations on hiring, role design, and performance management Call Quality & Conversion Improvement Define what “great” looks like on a sales callImprove:Discovery qualityObjection handlingOffer alignment and positioningEnsure ethical, high-integrity sales practices aligned with customer outcomesPersonally close deals (~10% capacity) to stay close to the process and model excellence Marketing, Events & Product Alignment Partner with Marketing to improve:Lead qualityApplication quality and scoringMessaging alignmentCreate clear handoffs between Marketing → Sales → CoachingCollaborate on funnel optimization (top → middle → bottom)Support strategy:Improve conversion from attendees to customersAlign upsell pathways and follow-upTranslate frontline sales insights into recommendations for Product and Coaching Data, Reporting & Continuous Improvement Build and maintain clear dashboards and reporting for leadership visibilityIdentify trends and performance drivers using dataRun structured experiments to improve:Show ratesClose ratesUpsell ratesMaintain a culture of iteration and accountability within the sales team Competencies Sales Leadership Proven ability to improve close rates and team performanceExperience managing setters/closers or multi-stage sales funnelsStrong 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 environmentsComfort owning CRM systems and data quality Coaching & Performance Development Skilled at giving direct, actionable feedbackAble to raise the floor and ceiling of team performanceComfortable holding contractors accountable without traditional authority structures Cross-Functional Collaboration Experience working closely with Marketing and Product teamsAbility to translate sales insights into actionable recommendationsStrong communication and alignment skills Strategic Thinking Can balance short-term revenue needs with long-term scalabilityIdentifies leverage points across the funnel (not just on the call) Key Metrics The Head of Sales is accountable for: Total Booked RevenueFlight Sales ClosesCoaching Sales ClosesStrategy 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 gapsTeam strengths and weaknessesBegin CRM audit (HubSpot) and identify major issuesStart call reviews and initial coaching feedbackIdentify top 2–3 leverage points impacting revenue First 90 Days Implement improvements to:Sales process and workflowsCRM structure and reportingCoaching and accountability systemsImprove consistency across repsEstablish clear KPI tracking and reporting cadenceBegin measurable improvements in show rate and/or close rate 6–12 Months Build a reliable, predictable sales engineImprove overall conversion rates and revenue per leadEstablish strong alignment with Marketing and ProductReduce performance variance across the teamCreate 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 environmentsExperience leading remote sales teamsStrong operator who can both build systems and execute within themComfortable 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). Skills: teaching, CRM, analytics, startup, R, hubspot, performance management, sales leadership