Lead Product Manager, Pilot Experience

At Flight Schedule Pro, we're transforming the flight training industry by empowering flight schools, pilots, and aviation professionals with technology and integrations that streamline operations, drive revenue, and accelerate pilot careers. With over 1,500 operators and strategic partnerships like Sallie Mae, we're at the forefront of modernizing aviation education and career development.

We’re building connected experiences that serve pilots from their first flight through their entire career journey. This role blends product strategy, product sense and strong zero-to-one product execution in a complex B2B2C ecosystem, and offers a rare opportunity to define the future of aviation training at scale. As the Lead Product Manager, Pilot Experience, you will be the strategic and execution engine behind this vision, owning problem definition, user insight, positioning, roadmap, and outcomes for a high-visibility product that touches thousands of pilots every day.

Responsibilities: 

• Own end-to-end product strategy, vision, and roadmap for the pilot experience, shaping a multi-year plan that drives meaningful user and business outcomes.
• Lead zero-to-one product development, from user discovery and problem definition through GTM, launch, iteration, and scaling.
• Drive engagement and habit formation, designing features that anchor daily, weekly, and monthly usage patterns for student pilots and instructors.
• Define and deliver clear outcomes, using activation, progression, engagement, and retention metrics to steer the team and validate product direction.
• Partner closely with engineering, UX and design to deliver elegant, high-quality features at a fast, consistent pace.
• Develop and refine GTM strategies, partnering with growth, marketing, and CS to craft positioning, messaging, activation flows, and pricing for new features and releases.
• Skillfully manage and influence highly opinionated stakeholders, integrating diverse perspectives into a cohesive strategy while maintaining forward momentum.
• Champion an AI-first approach, identifying opportunities where AI meaningfully accelerates user outcomes and product velocity.
• Navigate and create clarity in areas of high ambiguity, making crisp decisions using sound judgment, experience, and imperfect data.
• Elevate product quality across the team, setting the bar for UX, workflow clarity, and overall product craftsmanship.

Required/Desired Experience: 

• 7–10+ years of product management experience, with a proven track record of leading complex, high-impact, or zero-to-one product initiatives.
• Demonstrated ability to set strategy, prioritize effectively, and drive toward measurable outcomes.
• Experience building or optimizing habit-forming or engagement-focused product experiences.
• Deep product sense and discernment, with the ability to identify, design, and scale habit-forming features that drive sustained engagement.
• Strong GTM leadership experience - from positioning and messaging to activation, lifecycle, and revenue modeling.
• Exceptional communication and storytelling skills, capable of aligning executives, SMEs, and cross-functional leaders around a shared product vision.
• Comfort and confidence operating in a complex B2B2C environment, balancing the needs of multiple user types.
• Experience evaluating and applying AI technologies to enhance user value, streamline workflows, and accelerate development.
• Proven ability to make high-quality decisions with incomplete information, creating clarity and momentum across teams.
• Strong partnerships with engineering and design, with experience planning and delivering high-quality product increments at pace.

Helpful, but not required:

• Experience developing learning, progression, or marketplace products.
• Aviation industry background or a passion for flight
• Experience operating in regulated or safety-critical environments.

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 salary range for this role has been established at $165,000-$190,000 annually. 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.

Flight Schedule Pro 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. Flight Schedule Pro 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.

Flight Schedule Pro welcomes all direct applicants, but does not utilize recruiting services from external agencies.