Lead Product Manager, Pilot Experience

Flight Schedule Pro is transforming the flight training industry with technology that empowers flight schools, pilots, and aviation professionals. The Lead Product Manager, Pilot Experience will own the product strategy and execution for the pilot experience, driving engagement and retention while collaborating with cross-functional teams to deliver high-quality product increments.

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

Requirements:

• 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
• 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