Head of Sales, Flight Schools Solutions
About The Position
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, and category leadership. This role will help shape how Pilotbase scales commercially during that transition. 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, and category leadership. This role combines sales leadership, strategic deal ownership, GTM systems development, operational accountability, and cross-functional orchestration. The Head of Sales will directly manage Account Executives, expansion/account management functions, sales process execution, forecasting discipline, outbound development strategy, and enterprise and university sales motions. This role reports directly to the CRO.
Requirements
- Modern commercial leader who combines operational rigor, strategic thinking, coaching ability, enterprise sales judgment, and hands-on execution
- Ability to build systems that scale while maintaining strong customer trust and organizational alignment
- Comfortable operating in industries where relationships matter, operational credibility matters, customer outcomes matter, and long-term ecosystem value matters
- Thrives in environments where ambiguity exists, processes are still evolving, speed matters, and cross-functional partnership is essential
- Balances strategic thinking with execution, accountability with empathy, and process discipline with adaptability
- 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
- Enterprise SaaS commercial leadership combined with aviation familiarity, institutional selling experience, or workforce-development domain knowledge
- Pilot experience
- Experience selling into aviation organizations
- Experience selling into higher education institutions
- Experience managing consultative, operational sales environments
Responsibilities
- 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
- 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
- Partner closely with the Pilotbase Adoption & Growth Lead role to shape scalable expansion motions tied to Pilotbase Pilot adoption, safety suite deployment, pilot subscriptions, connected pilot experiences, and future ecosystem services
- Ensure alignment between Sales, Customer Success, Lifecycle Marketing, Product, and Implementation
- 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
- Partner closely with Marketing, Product, RevOps, Customer Success, and Executive Leadership
- Ensure strong alignment between product strategy, market positioning, expansion opportunities, customer adoption, and revenue outcomes
Benefits
- Eligibility for variable compensation
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
