The Director of Product Packaging and Pricing is responsible for defining and evolving Frontline’s packaging, pricing, and monetization strategy to drive customer value and sustainable growth. This leader partners closely with Product Management, Product Design, Engineering, Finance, Sales, Marketing, and Customer Success to ensure our offerings are easy to understand, easy to buy, and aligned to the outcomes customers seek.
Operating within Frontline’s empowered product model, this role provides strategy, frameworks, and decision support that enable product teams to make evidence-based tradeoffs across value, pricing, and go-to-market execution. You will use quantitative analysis, market insight, and customer learning to improve ARR, retention, conversion, and expansion while maintaining trust and transparency with districts.
AI experience is a plus; AI curiosity is a must. You will be expected to stay current on how AI can improve pricing analysis, packaging clarity, and customer experience, and to apply AI responsibly in your work.
Packaging and Monetization Strategy
• Own the packaging and pricing strategy across Frontline’s product ecosystem, ensuring clear value communication and scalable monetization.
• Define principles and decision frameworks for bundles, tiers, add-ons, modules, usage-based components, and cross-product packaging.
• Partner with product leaders to align packaging decisions to customer outcomes, product strategy, and measurable business results.
• Develop recommendations for new offerings and packaging changes, including business cases, risk assessments, and rollout plans.
Pricing, Deal Strategy, and Governance
• Establish pricing models and guardrails that balance value, competitiveness, simplicity, and profitability.
• Partner with Sales and Finance on deal strategy, discounting policy, approvals, and pricing governance to improve consistency and performance.
• Support key strategic deals with pricing guidance and value positioning while protecting long-term product health and pricing integrity.
• Maintain and evolve a pricing and packaging governance cadence, ensuring decisions are transparent, documented, and repeatable.
Customer, Market, and Competitive Insight
• Lead customer and market learning related to willingness to pay, value drivers, and packaging comprehension.
• Run and/or partner on research methods such as surveys, interviews, pricing studies, and win/loss analysis.
• Maintain competitive pricing and packaging intelligence and translate insight into actionable recommendations.
• Partner with Product Design to ensure packaging experiences are intuitive, accessible, and aligned to customer mental models.
Cross-Functional Go-to-Market Enablement
• Partner with Go-to-Market leaders to shape and refine the 'Better Together' narrative through packaging clarity and cross-product value articulation.
• Collaborate with Marketing and Sales Enablement to produce messaging, collateral, and tools that explain value, differentiation, and pricing confidently.
• Ensure packaging and pricing changes are operationally ready, including systems, quoting, training, and customer communications.
• Work with Customer Success to support renewals, expansions, and adoption strategies tied to packaging structure.
Measurement and Continuous Improvement
• Define and track success metrics for packaging and pricing initiatives, such as conversion, ARR, NRR, retention, expansion, win rate, and margin.
• Use experimentation and analytics to test hypotheses, learn quickly, and iterate responsibly.
• Create clear executive communications that connect packaging and pricing decisions to outcomes and tradeoffs.
• Customers and internal teams can clearly understand Frontline’s offerings and the value of each package and tier.
• Packaging and pricing changes drive measurable improvement in growth and retention metrics without eroding trust.
• Governance reduces pricing exceptions and improves deal consistency and predictability.
• Cross-product packaging reinforces platform value and the 'Better Together' narrative.
• Decisions are evidence-based, transparent, and aligned to customer outcomes and business performance.
Qualifications and Attributes
• 8+ years of experience in product management, monetization, pricing, strategy, or related roles within SaaS or enterprise software.
• Demonstrated success leading packaging and pricing initiatives that improved measurable business outcomes.
• Strong analytical skills, including comfort with financial models, segmentation, cohort analysis, and experimentation.
• Ability to translate complex analysis into clear recommendations, narratives, and stakeholder decisions.
• Proven cross-functional influence with Product, Finance, Sales, Marketing, and Customer Success leaders.
• Strong customer empathy and experience validating value through research and discovery methods.
• Experience with modern product practices including empowered teams, continuous discovery, and iterative delivery.
• AI experience is a plus; AI curiosity is a must, including willingness to learn and apply AI tools responsibly.
Our Mission, Our People, Our Purpose
At Frontline Education, we’re reimagining what’s possible by becoming an AI-first organization, transforming how we think, work, and serve the educators who shape our schools every day. By using AI in thoughtful, practical ways, we’re creating tools that help educators save time, gain insights, and focus more on what matters most — their students.
As part of our team, you’ll be expected and empowered to build and apply AI skillsets that grow with you, because at Frontline Education, technology amplifies what matters most: the human drive to learn, improve, and make a difference.
How We Support Growth, Balance, and Well-Being
- 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.
Continuous Learning and Growth
- 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.
Health, Happiness, and Purpose
- 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.
Compensation & Benefits
The salary range for this role is $170,000 - $220,000 per year, based on experience, skills, and internal equity. In addition to base salary, this role includes a bonus, personalized PTO, and comprehensive benefits, including health insurance, 401k, and much more!
Inclusion, Belonging & Equal Opportunity
Frontline Education is an equal opportunity/affirmative action employer. We aspire to have an inclusive workplace and strongly encourage suitably qualified applicants from a wide range of backgrounds to apply and join our team.
Interview Process & Data Privacy
As part of our interview process, Frontline uses video conferencing tools that include photo capture and may include automated transcription features. A screenshot or photo will be taken at the start of the interview for internal identification and record-keeping purposes only, and transcription may be used to support notetaking and evaluation consistency. These materials are used solely by our recruiting and hiring teams, stored securely, and not shared outside the hiring process. Candidates may opt out of the transcription at any time by notifying their recruiter in advance. Frontline processes this information in accordance with applicable data privacy laws and only for legitimate business purposes related to recruitment and hiring.
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