Director of Product, Pricing and Packaging

• Define and drive the multi-year strategy for Frontline’s packaging and pricing model across the product portfolio, balancing customer value, business growth, and operational scalability. 
• Serve as the company’s expert on monetization strategy by connecting product value to pricing architecture, segmentation, and market opportunity. 
• Partner with Product and Finance leadership to inform investment decisions, lifecycle management, and market expansion priorities. 
• Establish clear success metrics that link packaging and pricing decisions to revenue, retention, and adoption outcomes. 
• Act as a thought partner to the CPO and ELT by bringing forward insights that shape corporate strategy and product evolution. 

• Lead continuous discovery to understand customer perception of value, price sensitivity, and adoption drivers. 
• Collaborate with Product Managers, Product Design, and Marketing to test packaging hypotheses through surveys, interviews, and pricing experiments. 
• Leverage behavioral and usage data to identify opportunities to simplify, differentiate, or expand offerings. 
• Ensure customer insights directly inform how we define and communicate product value. 

• Partner with Finance, Sales, and Marketing to operationalize pricing and packaging strategies in go-to-market execution. 
• Collaborate with Product Managers to align packaging decisions with roadmap priorities and feature investments. 
• Build scalable frameworks and processes for pricing analysis, testing, and iteration. 
• Enable field teams with the tools, positioning, and confidence to articulate value effectively and consistently. 
• Coordinate pricing and packaging governance across the organization to ensure decisions are transparent, data-informed, and aligned with company objectives.   

• Introduce modern pricing methodologies such as value-based, usage-based, and outcome-based models to evolve Frontline’s approach. 
• Design and run controlled experiments to test elasticity, new bundles, or alternative commercial models. 
• Explore how emerging technologies, including AI-driven personalization and analytics, can enhance monetization strategy. 
• Foster a test-and-learn culture that empowers teams to iterate based on evidence rather than assumption. 
• Leverage AI and data-driven insights to model pricing elasticity, uncover customer value patterns, and improve decision-making across the portfolio. 

• Lead through context, not control, by ensuring cross-functional alignment through transparency, clear goals, and shared outcomes. 
• Communicate complex pricing and product concepts clearly to both executives and frontline teams. 
• Build trust across diverse stakeholders, balancing financial, operational, and customer considerations. 
• Coach and mentor team members and cross-functional partners in value-based thinking and discovery practices. 

• Frontline’s product portfolio has clear, differentiated packaging that communicates customer value. 
• Pricing strategy drives both growth and retention while maintaining equity and simplicity for customers. 
• Teams across Product, Sales, and Finance are aligned around shared metrics and decision frameworks. 
• Experiments and insights continuously inform how Frontline evolves its monetization model. 
• You are seen as a trusted, data-driven strategic partner who helps the company scale sustainably. 

• 8–12 years of experience in Product Management, Product Strategy, or Monetization roles within SaaS or enterprise software. 
• Proven success designing and implementing scalable packaging and pricing strategies across complex product portfolios. 
• Strong analytical and financial acumen with comfort in data modeling, sensitivity analysis, and business case development. 
• Deep understanding of customer value discovery, pricing research, and experimentation methods. 
• Excellent cross-functional collaboration and communication skills, with the ability to influence at all levels. 
• Demonstrated experience partnering with Product, Finance, Marketing, and Sales to deliver measurable results. 
• Entrepreneurial mindset with the ability to balance strategic vision and hands-on execution. 
• Curiosity for emerging business models and technologies, particularly AI’s role in optimizing customer and revenue outcomes. 
• Embodies Frontline’s leadership principles: customer obsession, ownership, innovation, and collaboration. 

• Personalized Time Off: Take time when it’s needed most — whether that’s a family vacation, a reset day, or simply time to rest and refocus. 
• Paid Sick Time: Separate, dedicated sick leave to care for yourself or loved ones. 
• Volunteer Time Off: Paid time to give back and support causes that matter to you. 
• Ten Paid Holidays: Enjoy meaningful moments and traditions throughout the year. 
• Our Philosophy: We believe time away from work helps you bring your best self to it. 

• World-Class Learning Access: Explore thousands of on-demand courses through platforms like LinkedIn Learning. 
• Leadership & Technical Skill Building: Develop new capabilities and chart your own professional path. 
• AI Empowerment: Use OpenAI tools to build fluency with emerging technology and harness AI as a creative partner for innovation and problem-solving. 
• Tuition Reimbursement: Invest in formal education to advance your skills and career. 
• Ongoing Learning Culture: Participate in company-led webinars on AI, inclusion, and industry trends—designed to inspire curiosity and continuous improvement. 

• Wellness Initiatives: Company-sponsored programs that support physical, mental, and emotional well-being. 
• Employee Assistance Program (EAP): Confidential support for you and your family’s needs. 
• Comprehensive Benefits: Health and financial benefits that support your happiness and future. 
• A Culture That Cares: At Frontline Education, we want every team member to learn, grow, and thrive—personally, professionally, and purposefully.