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Head of Sales, Flight Schools Solutions

Overland Park, Remote - United States

About Pilotbase

Pilotbase is building the connected operating system for pilot development.

Through Flight Schedule Pro and LogTen, our products support more than 1,400 flight schools, thousands of instructors, and a growing network of pilots across every stage of the aviation journey. We are now entering our next phase of growth: expanding from operational software into a connected ecosystem that links training, safety, financing, pilot progression, and career opportunity across aviation.

As we scale, we are evolving our commercial organization to support:

  • deeper enterprise engagement
  • installed-base expansion
  • pilot-facing growth
  • connected ecosystem expansion
  • category leadership

This role will help shape how Pilotbase scales commercially during that transition.

About the Role

Pilotbase is hiring a Head of Sales to lead the next evolution of our commercial organization.

This is a hands-on sales leadership role for someone who thrives in modern SaaS environments, values operational rigor, and knows how to build scalable revenue systems without overcomplicating the process.

You will inherit a lean, capable commercial team and help evolve it into a disciplined, high-performing revenue organization capable of supporting:

  • enterprise expansion
  • installed-base growth
  • pilot ecosystem adoption
  • strategic partnerships
  • category leadership

This role combines:

  • sales leadership
  • strategic deal ownership
  • GTM systems development
  • operational accountability
  • cross-functional orchestration

The Head of Sales will directly manage:

  • Account Executives
  • expansion/account management functions
  • sales process execution
  • forecasting discipline
  • outbound development strategy
  • enterprise and university sales motions

This role reports directly to the CRO.

What You’ll Own & Build

Commercial Leadership & Team Management

  • Lead and coach a small but growing commercial team
  • Establish accountability, forecasting rigor, and operational discipline
  • Improve pipeline hygiene, qualification consistency, and deal progression
  • Build scalable sales operating rhythms including:
    • forecast reviews
    • pipeline inspection
    • deal desk management
    • KPI accountability
  • Support hiring and development of future sales and account management talent

Enterprise & Strategic Sales

  • Personally own strategic and enterprise opportunities
  • Lead complex university and large-fleet sales cycles
  • Support high-value expansion opportunities across the installed base
  • Improve value-based and consultative selling execution
  • Reduce reliance on executive escalation during complex deals

Installed-Base Expansion Strategy

  • Partner closely with the Pilotbase Adoption & Growth Lead role
  • Help shape scalable expansion motions tied to:
    • Pilotbase Pilot adoption
    • safety suite deployment
    • pilot subscriptions
    • connected pilot experiences
    • future ecosystem services
  • Ensure alignment between:
    • Sales
    • Customer Success
    • Lifecycle Marketing
    • Product
    • Implementation

Outbound & Revenue Systems

  • Build scalable outbound and territory development strategies
  • Operationalize AI-assisted BDR workflows and lead qualification systems
  • Improve segmentation, targeting, and enterprise prioritization
  • Drive efficiency across inbound and outbound motions

Cross-Functional GTM Leadership

  • Partner closely with:
    • Marketing
    • Product
    • RevOps
    • Customer Success
    • Executive Leadership
  • Ensure strong alignment between:
    • product strategy
    • market positioning
    • expansion opportunities
    • customer adoption
    • revenue outcomes

Who You Are

You are a modern commercial leader who combines:

  • operational rigor
  • strategic thinking
  • coaching ability
  • enterprise sales judgment
  • hands-on execution

You know how to build systems that scale while maintaining strong customer trust and organizational alignment.

You are comfortable operating in industries where:

  • relationships matter
  • operational credibility matters
  • customer outcomes matter
  • long-term ecosystem value matters

You thrive in environments where:

  • ambiguity exists
  • processes are still evolving
  • speed matters
  • cross-functional partnership is essential

You balance:

  • strategic thinking with execution
  • accountability with empathy
  • process discipline with adaptability

Preferred Background

Strong candidates will likely bring experience from one or more of the following environments:

  • aviation software or operations
  • flight training or workforce development
  • higher education or enrollment lifecycle systems
  • operational or vertical SaaS platforms
  • multi-product or ecosystem-driven SaaS businesses

We are especially interested in candidates who combine:

  • enterprise SaaS commercial leadership
    with
  • aviation familiarity, institutional selling experience, or workforce-development domain knowledge

Ideal candidates may have:

  • pilot experience
  • experience selling into aviation organizations
  • experience selling into higher education institutions
  • experience managing consultative, operational sales environments

What Success Looks Like

Sales Operations & Execution

  • Predictable forecasting and cleaner pipelines
  • Strong qualification discipline
  • Improved conversion efficiency across the funnel
  • Consistent operating cadence across the commercial organization

Team Performance

  • Confident sellers operating with clarity and accountability
  • Improved sales velocity and deal progression
  • Strong collaboration across Sales, CS, Marketing, and Product

Strategic Growth

  • Strong execution on enterprise and university opportunities
  • Improved expansion performance inside the installed base
  • Operational readiness for scalable Pilotbase adoption and ecosystem expansion

Organizational Maturity

  • Reduced executive dependency in day-to-day deal execution
  • Sales systems built to scale
  • Improved visibility into performance against modeled expectations

Compensation

The base salary range for this role has been established at $165,000 - $180,000 annually, plus eligibility for variable compensation. The final agreed-upon compensation is based on a number of factors, including but not limited to: individual education, qualifications, skills, prior work experience, competencies, and geographic work location. The above salary range represents the Company’s good faith and reasonable estimate of the range of possible compensation at the time of posting.

Why This Role Matters

Pilotbase is evolving from a category-leading flight school operating system into a broader pilot development ecosystem.

This role will help shape:

  • how aviation training organizations adopt new operational technologies
  • how Pilotbase expands within its installed base
  • how pilots engage with the broader ecosystem
  • how enterprise and institutional relationships scale
  • how the next generation of aviation infrastructure is adopted and scaled

You’ll help define not only how we sell, but how the aviation industry becomes more connected over the next decade.

 

Pilotbase is an equal opportunity employer and encourages all qualified individuals to apply. If you're excited about this role, we'd love a chance to review your resume. We value a diverse and inclusive work environment and look for passionate people who are ready to do great things. If there is a required or preferred location for an open role, it will be listed in the job description. All applicants for employment must be legally authorized to work in the United States. Pilotbase does not provide work visa sponsorship at this time.

This employer participates in the Electronic Employment Verification Program. Please visit https://www.e-verify.gov/about-e-verify for more information.

Pilotbase welcomes all direct applicants, but does not utilize recruiting services from external agencies.

 

 

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