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).

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