Flight Schedule Pro powers the world’s flight training ecosystem, supporting over 1,400 flight schools and tens of thousands of pilots each year.
We are now building Pilotbase, a connected system that brings together flight schools, pilots, and industry partners into a single, data-driven network. This next phase of growth is focused on expanding within our existing customer base, reaching pilots directly, and creating new revenue streams across the ecosystem.
Role Overview and Responsibilities:
We are hiring a Pilotbase Growth & Adoption Lead to drive how Pilotbase is introduced, adopted, and expanded across our flight school customer base—and how that adoption translates into long-term revenue.
This role sits at the intersection of product, revenue, and customer strategy. You will define how we grow through our customers to reach pilots, shape early monetization models, and build repeatable adoption and expansion playbooks.
Drive Pilotbase Adoption
Lead adoption of Pilotbase across flight school customers
Define how schools introduce and operationalize Pilotbase within training programs
Partner with Customer Success to ensure strong onboarding, engagement, and retention
Develop Monetization Strategy
Contribute to pricing and packaging strategy across multiple models (B2B, B2B2P, and direct-to-pilot)
Test and validate pilot subscription and usage-based revenue opportunities
Build the foundation for scalable monetization tied to adoption and engagement
Expand Within Existing Customers
Identify and execute expansion opportunities tied to Pilotbase adoption
Support Sales in positioning Pilotbase within new logo and upsell motions
Develop repeatable playbooks for integrating Pilotbase into multi-product deployments
Lead Cross-Functional Execution
Partner with Sales, Customer Success, Product, and Marketing to align on adoption and growth strategy
Translate customer and pilot behavior into actionable insights for product and GTM teams
Ensure alignment between pilot engagement and flight school value
Connect Adoption to Revenue Outcomes
Define how adoption and usage drive retention, expansion, and new revenue streams
Establish early frameworks linking engagement to monetization
Help shape the long-term growth model for Pilotbase
What Success Looks Like
Strong Pilotbase adoption across the flight school customer base
Clear, validated pricing and packaging direction
Repeatable adoption and expansion playbooks
Measurable connection between pilot engagement and revenue outcomes
Early traction in pilot subscription or usage-based monetization
Qualifications:
Required
Experience in SaaS, marketplace, or platform-based business models
Exposure to pricing, packaging, or monetization strategy
Proven ability to work cross-functionally across Sales, Product, Marketing, and Customer Success
Strong analytical and strategic thinking, with the ability to translate insight into execution
Preferred
Experience in product-led or hybrid go-to-market models
Background in growth, expansion, or revenue strategy roles
Experience in multi-sided platforms or subscription-based businesses
How You Work:
Operate comfortably in ambiguity and build from first principles
Balance strategic thinking with hands-on execution
Focus on measurable outcomes over activity
Communicate clearly across technical and commercial stakeholders
Benefits:
Full benefits package (Medical, Dental, Vision, Short-Term Disability, Life Insurance, 401(k) plan)
Equity Appreciation Plan
Flexible Time Off policy
Seven (7) company-wide paid holidays + two (2) floating holidays
Two (2) wellness days
Employee Assistance Program
Professional Development Stipend
Home Office Stipend
Compensation:
The base salary range for this role has been established at $105,000 - $115,000 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.
Travel Requirements:
Occasional business travel may be required, up to 10%.
Deadline for Applications:
The company will accept ongoing applications until the role is filled. There is no deadline to apply for this position.
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.