Head of Sales

The Head of Sales is responsible for building a predictable, scalable, and high-integrity sales function that consistently converts qualified leads into successful customers.

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, reducing 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 (approximately 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; 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

Key Metrics

• Total Booked Revenue
• Flight School Sales Closes
• Coaching Sales Closes
• Strategy Sessions and Show-Up Rates

Success in Role

• 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

• 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).