Head of Sales, Flight Schools Solutions

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.