Sr Director, Product Strategy

📍 Job Overview

Job Title: Sr Director, Product Strategy

Company: PowerSchool Group LLC

Location: Dallas, TX / Remote (US)

Job Type: Full-Time

Category: Product Management & Strategy (GTM Focus)

Date Posted: May 22, 2026

Experience Level: 10+ Years

Remote Status: Hybrid (with remote option for US-based candidates)

🚀 Role Summary

• Define and execute multi-year product strategy for critical analytics product lines, focusing on market competitiveness and revenue growth.

• Lead comprehensive go-to-market (GTM) planning, encompassing launch strategies, sales enablement, and international market entry initiatives.

• Drive product positioning, pricing, and SKU rationalization to optimize the product portfolio's market appeal and profitability.

• Foster strong cross-functional collaboration across Product, Sales, Marketing, and Professional Services to ensure seamless product delivery and customer success.

• Leverage data analysis and market intelligence to identify growth opportunities, inform strategic decisions, and measure product performance.

📝 Enhancement Note: This role is a senior leadership position within Product Management, with a significant emphasis on Go-To-Market (GTM) strategy and execution for analytics products. The "Sr Director" title, combined with responsibilities like GTM planning, sales enablement, and cross-functional leadership, indicates a strategic and influential role crucial for translating product vision into market success. The focus on B2B SaaS and K-12 education technology suggests a need for deep domain expertise and a proven ability to manage complex product portfolios.

📈 Primary Responsibilities

• Product Strategy & Vision:

  • Define and champion the multi-year product strategy for analytics product lines, aligning with company objectives and market demands.
  • Lead SKU rationalization, product composition, and pricing initiatives to enhance portfolio clarity and competitive advantage.
  • Develop and manage a prioritized product roadmap, securing stakeholder buy-in and ensuring alignment with strategic goals.
  • Conduct in-depth competitive analysis, developing robust cross-block (X-block) positioning against key market rivals.

• Go-To-Market Execution:

  • Spearhead GTM planning, including defining launch strategies, executing sales enablement programs, and managing market entry for new territories (states and international).
  • Create and maintain essential sales tools such as pitch decks, digital sales rooms, and decision trees to empower the sales force.
  • Collaborate closely with Sales, Marketing, and Solution Consulting teams to accelerate pipeline growth and improve conversion rates.
  • Analyze market data (e.g., GovSpend), contract lifecycles, and win/loss reports to identify and capitalize on growth targets.

• Cross-Functional Leadership:

  • Facilitate and lead Senior Leadership Team (SLT) meetings, responsible for agenda setting, action item tracking, and driving accountability across departments.
  • Partner with Professional Services to refine implementation scoping, customer onboarding processes, and deployment Standard Operating Procedures (SOPs).
  • Work with Support and Technical teams to enhance the post-sale customer experience and drive product adoption.
  • Coordinate international channel partner strategy, engagement, and performance management.

• Data & Analysis:

  • Conduct quantitative analyses on customer performance, churn rates, and expansion opportunities to inform strategic decisions.
  • Develop and maintain sophisticated Excel models to support business cases, financial projections, and strategic recommendations.
  • Build and track acquisition target lists and pipeline reports to guide sales strategy and resource allocation.

• Stakeholder Communication:

  • Present strategic updates, critical initiative reviews, and performance metrics to the executive leadership team.

  • Produce clear, concise documentation, including transition plans, strategy decks, and roadmap materials for various audiences.

  • Act as a key liaison and connector between Product, Sales, and Services leadership to ensure cohesive strategy execution.

📝 Enhancement Note: The responsibilities highlight a strategic GTM focus rather than pure product development. This role requires a leader who can bridge product capabilities with market realities, drive revenue through strategic packaging and sales enablement, and manage complex cross-functional initiatives. The emphasis on analytics product lines and K-12 EdTech suggests a need for domain expertise and a data-driven approach to strategy.

🎓 Skills & Qualifications

Education:

• Bachelor's degree required.

Experience:

• Minimum of 10+ years of progressive experience in product management, product strategy, GTM leadership, or a closely related field within the B2B SaaS industry.

• Demonstrated success in leading and executing cross-functional go-to-market initiatives for complex B2B SaaS products.

• Proven ability to define and drive product strategy, including roadmap development, SKU rationalization, and pricing initiatives.

Required Skills:

• Product Strategy & Roadmapping: Ability to define long-term product vision, develop prioritized roadmaps, and align with overarching business goals.

• Go-To-Market (GTM) Planning: Expertise in developing and executing comprehensive GTM strategies for SaaS products, including launch planning and sales enablement.

• Pricing & Packaging: Skilled in SKU rationalization, product composition, and developing effective pricing models for B2B SaaS portfolios.

• Competitive Analysis: Proficient in conducting market and competitive research to inform product positioning and strategy.

• Cross-Functional Leadership: Proven ability to lead, influence, and collaborate effectively with diverse teams (Product, Sales, Marketing, Services, Engineering).

• Analytical & Data Modeling: Strong quantitative skills with expertise in data modeling, pipeline analysis, financial modeling (Excel), and deriving actionable insights from data.

• Executive Communication & Presentation: Exceptional ability to articulate complex strategies, present data-driven recommendations, and influence senior leadership.

• Stakeholder Management: Adept at managing relationships and driving alignment across various internal and external stakeholders.

Preferred Skills:

• K-12 Education Technology: Familiarity with the K-12 education technology landscape, including Student Information Systems (SIS), EdTech product ecosystems, and public sector software procurement.

• Business Intelligence (BI) & Analytics Tools: Experience with BI tools and advanced analytics applications (e.g., Tableau, Power BI, Looker) is a plus.

• International Market Expansion: Experience with developing and executing strategies for international market entry and channel partner programs.

• CRM & Project Management Tools: Proficiency with standard B2B SaaS tools such as Salesforce, Atlassian Suite (Jira, Confluence), and Microsoft Office/SharePoint.

• GovSpend Data Analysis: Experience utilizing procurement data sources like GovSpend to inform sales and product strategy.

📝 Enhancement Note: The qualifications emphasize a blend of strategic product leadership, strong GTM execution capabilities, and analytical rigor. Experience in the K-12 EdTech sector is highly valued, suggesting a need for domain-specific knowledge. The preference for an MBA or advanced degree, combined with extensive experience, points to a senior-level role demanding significant strategic thinking and leadership.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• GTM Strategy Case Studies: Examples of successful Go-To-Market plans developed and executed for B2B SaaS products, detailing market entry, launch activities, and sales enablement strategies.

• Product Strategy & Roadmap Examples: Demonstrations of strategic product planning, including multi-year roadmaps, competitive positioning against rivals, and clear prioritization frameworks.

• Pricing & Packaging Documentation: Evidence of experience in SKU rationalization, product composition, and developing pricing models that drive revenue and market adoption.

• Cross-Functional Initiative Leadership: Case studies showcasing the ability to lead complex, cross-departmental initiatives, highlighting collaboration with Sales, Marketing, and Services to achieve shared objectives.

• Data Analysis & Business Case Development: Examples of quantitative analyses, financial models (e.g., Excel), and business cases developed to support strategic recommendations or investment decisions.

Process Documentation:

• Strategic Planning Workflows: Documented processes for defining product strategy, developing roadmaps, and securing executive alignment.

• GTM Launch Frameworks: Standardized processes for planning and executing product launches, including sales enablement, marketing coordination, and market entry.

• Pricing & SKU Rationalization Methodologies: Defined approaches for analyzing product portfolios, rationalizing SKUs, and establishing competitive pricing structures.

• Cross-Functional Collaboration Protocols: Established methods for facilitating communication and driving accountability across Product, Sales, Marketing, and Services teams.

• Data Analysis & Reporting Procedures: Documented workflows for conducting quantitative analysis, building financial models, and generating performance reports for strategic decision-making.

📝 Enhancement Note: While not explicitly stated, a role at this seniority level, particularly in Product Strategy and GTM, typically requires candidates to demonstrate their experience through a portfolio. This portfolio should showcase strategic thinking, execution capabilities, and impact on revenue. The focus is on strategic planning, market execution, and cross-functional leadership, with a strong emphasis on data-driven decision-making and demonstrable results.

💵 Compensation & Benefits

Salary Range:

Benefits:

• Comprehensive Health & Wellness:

  • Medical, Dental, and Vision Insurance coverage.
  • Pharmacy benefits.
  • Flexible Spending Accounts (FSAs) and Health Savings Accounts (HSAs).
  • Wellness Program, including ClassPass and Employee Assistance Program (EAP).

• Income Protection:

  • Life Insurance and Accidental Death & Dismemberment (AD&D) Insurance.
  • Short-Term Disability (STD) and Long-Term Disability (LTD).

• Retirement Savings:

  • Comprehensive 401(k) plan.

• Time Off & Leave:

  • Generous Parental Leave.
  • Unrestricted paid time off (Discretionary Time Off - DTO).

• Professional Development:

  • Tuition Reimbursement.

• Additional Perks: Working Hours:

• Standard full-time employment is typically 40 hours per week. While not explicitly stated, senior leadership roles often require flexibility to meet business needs, including occasional work outside standard business hours for critical initiatives or international collaboration.

📝 Enhancement Note: The provided salary range is specific to the US and is presented as an estimate. The breadth of benefits offered is extensive, covering health, wellness, income protection, retirement, and professional development, which is typical for senior-level positions in established tech companies. The "Discretionary Time Off" policy suggests a results-oriented culture that trusts employees to manage their workload effectively.

🎯 Team & Company Context

🏢 Company Culture

Industry: Education Technology (EdTech), specifically focused on K-12 education software solutions. PowerSchool is a global leader in cloud-based software serving the entire educational ecosystem.

Company Size: PowerSchool is a large organization, indicated by its extensive product portfolio and global presence. The company is publicly traded, suggesting a structured corporate environment with established processes and a focus on growth and shareholder value.

Founded: PowerSchool was founded in 1997, indicating a mature company with a long history and significant experience in the EdTech market.

Team Structure:

• Product Management Organization: This role sits within a larger Product Management organization, likely comprising various product teams focused on different areas of the PowerSchool platform.

• Reporting Structure: As a Sr Director, this role will likely report to a VP or SVP of Product Management or a related executive. The role will also manage a team of product managers and/or strategists, and will have significant interaction with other senior leaders across the company.

• Cross-Functional Collaboration: The role is explicitly positioned at the intersection of Product, Sales, Marketing, and Professional Services, highlighting a highly collaborative and integrated operational model.

Methodology:

• Data-Driven Decision Making: The emphasis on quantitative analysis, pipeline reports, and business case development indicates a strong reliance on data to inform strategy and measure success.

• Agile & Iterative Development Principles: While not explicitly stated, modern SaaS companies like PowerSchool typically employ agile methodologies for product development, with a focus on continuous improvement and iterative releases.

• Customer-Centric Approach: The focus on customer performance, adoption, and post-sale experience suggests a commitment to understanding and serving customer needs.

Company Website: www.powerschool.com

📝 Enhancement Note: PowerSchool's established presence in the K-12 EdTech market and its focus on cloud-based solutions position it as a significant player. The company culture likely values innovation, collaboration, and a commitment to improving educational outcomes. The role's strategic emphasis suggests an environment where leadership and influence are key to driving product success.

📈 Career & Growth Analysis

Operations Career Level: This is a Sr. Director level position, indicating a senior leadership role with significant strategic responsibility and likely direct reports. It requires a seasoned professional with extensive experience in product strategy and GTM execution, capable of influencing executive-level decisions and driving large-scale initiatives.

Reporting Structure: The Sr. Director will report to a higher-level executive within the Product organization (e.g., VP of Product, Chief Product Officer). They will be responsible for leading and mentoring a team of Product Managers and/or Product Strategists, and will work closely with peers in Sales, Marketing, Engineering, and Professional Services.

Operations Impact: This role has a direct and substantial impact on revenue generation and market share. By defining product strategy, optimizing pricing and packaging, and driving effective GTM execution, the Sr. Director directly influences sales pipeline, customer acquisition, expansion revenue, and overall market positioning of PowerSchool's analytics products.

Growth Opportunities:

• Leadership Advancement: Potential to progress to VP or SVP level roles within Product Management, overseeing larger product portfolios or broader strategic functions.

• Strategic Influence: Opportunity to shape the long-term direction of PowerSchool's analytics offerings and contribute significantly to the company's overall growth strategy.

• Cross-Functional Expertise: Deepen expertise across critical business functions including sales, marketing, finance, and operations through extensive collaboration.

• Industry Impact: Contribute to the advancement of K-12 education through strategic product innovation and effective market delivery.

• Mentorship & Team Development: Opportunity to build and mentor a high-performing product strategy team.

📝 Enhancement Note: This role represents a significant career opportunity for experienced product leaders. The combination of strategic product ownership, GTM responsibility, and leadership of a team offers a clear path for advancement within a large, established EdTech company. The impact on revenue and market position is substantial, making it a high-visibility role with significant growth potential.

🌐 Work Environment

Office Type: The primary office location is Dallas, TX, with a remote option available for US-based candidates. This suggests a hybrid work model is supported, allowing for flexibility. The organizational structure as a large, publicly traded company likely means well-equipped office spaces designed for collaboration and productivity.

Office Location(s): Dallas, Texas, USA. The remote option implies that candidates from other US locations can be considered, provided they can travel to Dallas for key meetings as needed.

Workspace Context:

• Collaborative Environment: The role demands significant interaction with various departments, indicating a workplace that fosters cross-functional teamwork and open communication.

• Tools & Technology: Access to standard enterprise software and collaboration tools (e.g., Microsoft Office Suite, Salesforce, Jira, Confluence) is expected to support daily operations, analysis, and communication.

• Operations Team Interaction: Frequent engagement with product management teams, sales leadership, marketing teams, and professional services will be integral to the role.

Work Schedule: The standard working hours are 40 hours per week. However, as a senior leadership position with global responsibilities and cross-functional coordination, flexibility to work beyond standard hours may be required to accommodate different time zones and critical project deadlines.

📝 Enhancement Note: The hybrid work model, with a remote option for US-based employees, reflects modern work trends. The emphasis on collaboration suggests a dynamic environment where effective communication and teamwork are paramount for success in driving product strategy and GTM initiatives.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: HR or Recruiter call to assess basic qualifications, experience, and cultural fit.

• Hiring Manager Interview: In-depth discussion with the hiring manager (likely a VP or SVP of Product) focusing on strategic thinking, GTM experience, leadership capabilities, and domain knowledge.

• Cross-Functional Interviews: Meetings with key stakeholders from Sales, Marketing, and Professional Services to evaluate collaboration skills and understanding of their respective functions.

• Product Strategy/GTM Case Study: A take-home or live presentation exercise where the candidate is asked to analyze a product scenario, develop a strategy, or present a GTM plan. This is critical for evaluating strategic thinking and presentation skills.

• Executive Interview: Final interview with a senior executive (e.g., CPO, CEO) to assess overall strategic vision, leadership potential, and alignment with company leadership.

Portfolio Review Tips:

• Showcase GTM Success: Clearly articulate your role in developing and executing successful GTM strategies for B2B SaaS products. Quantify results (e.g., pipeline generated, revenue growth, market share increase).

• Highlight Strategic Planning: Present examples of product roadmaps, strategic initiatives, and pricing/packaging decisions you've led. Explain the rationale and impact.

• Demonstrate Analytical Rigor: Include examples of complex data analysis, financial modeling, and how insights drove strategic recommendations.

• Emphasize Cross-Functional Leadership: Provide evidence of your ability to lead and influence diverse teams to achieve common goals. Use STAR method (Situation, Task, Action, Result) for behavioral examples.

• Tailor to Analytics & EdTech: If possible, include portfolio items relevant to analytics products and the education sector to demonstrate domain understanding.

Challenge Preparation:

• GTM Case Study: Be prepared to analyze a target market, identify customer needs, define product positioning, outline a pricing strategy, and detail a launch plan. Practice presenting this concisely and persuasively.

• Strategic Scenario: Anticipate questions about market trends, competitive threats, and how you would adapt product strategy or GTM approaches.

• Leadership & Collaboration: Prepare examples demonstrating how you've managed teams, resolved conflicts, and driven alignment across departments.

• Data & Financial Acumen: Be ready to discuss how you use data for decision-making, build financial models, and assess the ROI of strategic initiatives.

📝 Enhancement Note: The interview process is likely rigorous, with multiple stages designed to assess strategic depth, GTM expertise, leadership, and collaboration skills. A strong portfolio is crucial for demonstrating practical application of these skills, especially for a role focused on strategy and execution. The case study component is a key differentiator.

🛠 Tools & Technology Stack

Primary Tools:

• CRM: Salesforce (for pipeline analysis, sales strategy, and GTM alignment).

• Product Management & Collaboration: Atlassian Suite (Jira for issue tracking, Confluence for documentation and knowledge sharing).

• Productivity Suite: Microsoft Office Suite (Excel for advanced modeling and analysis, PowerPoint for executive presentations, Word for documentation, SharePoint for collaboration).

• Analytics & Data Tools:

  • Business Intelligence (BI) Tools (e.g., Tableau, Power BI, Looker) for data visualization, dashboard creation, and performance tracking.
  • Advanced Analytics Applications (general proficiency expected).

• Market Intelligence: GovSpend (for analyzing public sector procurement data and identifying growth targets).

CRM & Automation:

• Salesforce: Expected proficiency for understanding sales processes, pipeline management, and GTM alignment.

• Potential Automation Tools: While not specified, familiarity with general marketing automation or workflow tools could be beneficial for GTM execution.

• Integration Tools: Understanding how different systems (CRM, product databases, analytics platforms) integrate to provide a unified view of customer and product performance.

📝 Enhancement Note: Proficiency with standard B2B SaaS tools like Salesforce, Jira, Confluence, and the Microsoft Office suite is essential. Experience with BI tools and specific market intelligence platforms like GovSpend is highly valued, especially given the role's focus on analytics products and public sector clients.

👥 Team Culture & Values

Operations Values:

• Data-Driven Decision Making: A strong emphasis on using data and analytics to inform strategic decisions, measure performance, and drive accountability.

• Customer Centricity: A commitment to understanding and meeting the needs of K-12 educational institutions, ensuring products deliver value and improve educational outcomes.

• Innovation & Continuous Improvement: A culture that encourages exploring new ideas, embracing change, and continuously optimizing product strategy and GTM execution.

• Collaboration & Transparency: Fostering an environment where teams work together effectively, share information openly, and support each other to achieve common goals.

• Accountability & Ownership: Encouraging individuals to take ownership of their areas of responsibility, drive initiatives forward, and be accountable for results.

Collaboration Style:

• Cross-Functional Integration: The role actively bridges Product, Sales, Marketing, and Services, requiring a highly collaborative approach to ensure seamless execution and unified messaging.

• Executive Engagement: Regular interaction with senior leadership necessitates clear, concise, and persuasive communication to influence strategic direction.

• Team Leadership: For direct reports, the style likely involves mentorship, empowerment, and fostering a high-performance team culture.

• Process-Oriented: A structured approach to planning, execution, and review is expected, particularly in defining and refining GTM processes and product strategies.

📝 Enhancement Note: PowerSchool's values likely reflect a blend of innovation, customer focus, and operational excellence, common in successful EdTech companies. The collaborative nature of this role means that strong interpersonal skills and the ability to build consensus across diverse teams are paramount.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating a Complex Product Portfolio: Managing and strategizing for multiple analytics product lines within a large, established EdTech company requires deep understanding and prioritization skills.

• Driving GTM Adoption Across Diverse Markets: Successfully launching and growing products in various US states and international markets, each with unique educational systems and procurement processes.

• Balancing Strategic Vision with Execution: Translating long-term product strategy into actionable GTM plans and ensuring their effective implementation by sales and marketing teams.

• Cross-Functional Alignment: Achieving consensus and driving accountability across departments that may have competing priorities or perspectives.

• Staying Ahead of EdTech Trends: Continuously adapting product strategy and GTM approaches to evolving educational technologies, data privacy regulations, and market demands.

Learning & Development Opportunities:

• Strategic Leadership Development: Opportunities to hone skills in executive communication, strategic planning, and large-scale initiative leadership.

• Deepening EdTech Expertise: Gaining deeper insights into the K-12 education market, its unique challenges, and the impact of technology on student outcomes.

• Global Market Exposure: Experience in international market expansion and channel partner management.

• Mentorship: Potential to be mentored by senior executives and to mentor junior product professionals.

• Industry Engagement: Opportunities to attend industry conferences and engage with key stakeholders in the education sector.

📝 Enhancement Note: This role offers significant challenges that are commensurate with its senior level, providing ample opportunities for professional growth. The ability to navigate complexity, drive consensus, and adapt to a dynamic market will be key to success and development.

💡 Interview Preparation

Strategy Questions:

• "Describe your process for developing a multi-year product strategy for a B2B SaaS analytics product. How do you prioritize initiatives and gain executive buy-in?" (Focus on structured approach, data utilization, stakeholder engagement)

• "Walk me through a successful GTM launch you led. What were the key components of your strategy, how did you enable the sales team, and what were the measurable results?" (Use STAR method, emphasize quantification of impact)

• "How would you approach SKU rationalization and pricing optimization for a portfolio of analytics products? What factors would you consider?" (Demonstrate analytical rigor, market understanding, and financial modeling skills)

• "Describe a time you had to align multiple cross-functional teams (e.g., Product, Sales, Marketing, Services) around a new product strategy or GTM initiative. What challenges did you face, and how did you overcome them?" (Highlight leadership, communication, and conflict resolution skills)

Company & Culture Questions:

• "What interests you about PowerSchool and our mission in K-12 education?" (Research company values, recent news, and demonstrate genuine interest)

• "How do you see your experience in B2B SaaS GTM applying to the EdTech market?" (Connect your experience to the specific industry context)

Portfolio Presentation Strategy:

• Structure: Organize your portfolio into clear sections (e.g., Strategy, GTM, Analysis, Leadership). For each example, use a consistent structure: Challenge/Objective, Your Role/Actions, Strategy/Process, Results/Impact.

• Quantify Everything: Use numbers, metrics, and KPIs to demonstrate the tangible impact of your work (e.g., revenue growth, market share increase, pipeline conversion improvement).

• Focus on GTM & Strategy: Highlight case studies that clearly demonstrate your ability to define strategy, plan and execute GTM initiatives, and drive revenue.

• Visuals: Use charts, graphs, and concise summaries to make your data-driven insights easy to understand.

• Narrative: Tell a compelling story for each portfolio item, highlighting your thought process, problem-solving skills, and leadership.

📝 Enhancement Note: Preparation should focus on demonstrating strategic thinking, GTM execution expertise, strong analytical skills, and cross-functional leadership. The portfolio is a critical tool to showcase past successes, and candidates should be ready to present it confidently, highlighting quantifiable results and strategic rationale.

📌 Application Steps

To apply for this operations position:

• Submit your application through the PowerSchool careers portal via the provided link.

• Tailor Your Resume: Customize your resume to highlight experience in product strategy, GTM execution, B2B SaaS, analytics products, and any relevant EdTech or public sector experience. Use keywords from the job description (e.g., GTM strategy, product positioning, SKU rationalization, sales enablement, data modeling).

• Develop Your Portfolio: Prepare a concise portfolio showcasing your most impactful work in product strategy and GTM. Focus on case studies with quantifiable results, demonstrating your strategic thinking, analytical skills, and leadership capabilities. Be ready to present key pieces during the interview process.

• Research PowerSchool: Thoroughly understand PowerSchool's products, target market (K-12 education), competitive landscape, and company mission. Familiarize yourself with their recent news and strategic direction.

• Prepare for Case Study: Anticipate a product strategy or GTM case study interview. Practice outlining market analysis, defining strategic objectives, proposing GTM plans, and presenting findings clearly and persuasively.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

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