Lead Product Manager, Pilot Experience

Overland Park - Remote, United States

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, strong product sense, and high-velocity execution in a complex B2B2C ecosystem. As the Lead Product Manager, Pilot Experience, you will step into a high-visibility product space with real momentum, real complexity, and real opportunity — and bring the energy, conviction, and execution strength to drive it forward.

This role is for someone who thrives in ambiguity, can get out in front of chaos, and can build strong conviction around where to go next — while staying flexible enough to pivot when new insights emerge.

Responsibilities: 

• Own end-to-end product strategy, vision, and roadmap for the pilot experience, building conviction around the highest-impact opportunities and driving measurable outcomes.
• Step into an existing product area, quickly assess performance against goals, identify gaps and opportunities, and define clear next steps.
• Operate like a builder and business owner — driving strategy, execution, rollout, and iteration as if you were running your own company.
• Lead cross-functional teams through ambiguity, bringing clarity, momentum, and strong decision-making in a fast-moving environment.
• Drive product development from discovery through delivery, including user research, problem framing, prioritization, experimentation, launch, and iteration.
• Design and deliver functionality-driven product experiences that pilots rely on — building features that become core to workflows, not just “nice-to-have” enhancements.
• Partner closely with engineering, UX and design to ship high-quality product increments at a consistent pace.
• Influence and align highly opinionated stakeholders while remaining a strong defender of your product POV when needed.
• Build and communicate strong product convictions while remaining flexible enough to adjust based on results, feedback, or shifting business needs.
• Drive engagement and retention through features that support pilot progression, motivation, and habit formation.
• Champion an AI-forward mindset, identifying where AI can accelerate pilot outcomes, reduce friction, and increase product velocity.
• Partner with marketing, growth, sales, and customer success to support rollout, adoption, and performance of new features.
• Help evolve team excellence by introducing sharper product thinking, better prioritization practices, and stronger execution systems.

Required/Desired Experience: 

• 7–12+ years of product management experience, with some flexibility depending on depth of ownership and demonstrated impact.
• Strong builder mentality — you’ve created products or major features from scratch and can point to what you owned end-to-end.
• Deep experience with B2C or B2C-like products, especially where user experience, engagement, and functionality are critical to success.
• Comfortable operating in a B2B2C ecosystem (flight schools + pilots + instructors), balancing multiple user needs while keeping the pilot experience world-class.
• Proven ability to operate with conviction and confidence in a high-ambiguity environments
• Strong strategic thinking paired with hands-on execution — you can set vision and drive delivery.
• You can defend your product decisions, influence stakeholders, and navigate a highly opinionated environment without losing momentum.
• High ownership mindset — you naturally take responsibility for outcomes, not just deliverables.
• Strong stakeholder management skills with a track record of influencing cross-functional partners through data, narrative, and conviction.
• Appetite for AI — curiosity, experimentation, and comfort building AI-powered workflows into real product experiences.
• Experience shipping products where functionality is essential to daily usage, not optional.
• Strong communication and storytelling skills — you can align teams, execs, and partners around a clear narrative and roadmap.
• Comfortable in a company under 500 employees, where speed, autonomy, and accountability are essential.

Helpful, but not required:

• Experience with pricing, packaging, or monetization strategy.
• Experience owning multi-product ecosystems or product suites.
• Aviation industry experience or passion for flight training.
• Experience building 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 $190,000-$210,000 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.