VP of Product Strategy

📍 Job Overview

Job Title: VP of Product Strategy

Company: eSkill

Location: San Antonio, Texas, United States

Job Type: Full-time

Category: Product Strategy & Operations

Date Posted: May 31, 2026

Experience Level: Senior (10+ years)

Remote Status: On-site

🚀 Role Summary

• Drive the strategic direction and long-term product vision for a comprehensive B2B SaaS pre-hire assessment platform.

• Lead deep customer research and discovery initiatives to identify unmet needs and market opportunities.

• Define and prioritize product roadmap initiatives, ensuring alignment with business goals and customer value.

• Partner closely with executive leadership and engineering to translate strategic insights into actionable product requirements.

• Establish frameworks for measuring product success and driving outcome-oriented product thinking.

📝 Enhancement Note: This role is positioned as a senior leadership position within Product Strategy, focusing on the "what" and "why" of product development rather than the "how" of daily engineering execution. The emphasis is on strategic influence, customer understanding, and roadmap prioritization, requiring a leader who can bridge high-level vision with practical execution realities, especially in a distributed team environment.

📈 Primary Responsibilities

• Spearhead customer research, including leading interviews and feedback programs, to serve as the primary voice of the customer within the product organization.

• Define and articulate long-term product direction and roadmap priorities in close collaboration with the CEO and Director of Product Development.

• Analyze market trends, competitor landscapes, and emerging opportunities within the HR tech and talent acquisition sectors to inform strategic product decisions.

• Develop and implement frameworks for measuring product success, ensuring decisions are data-informed and focused on measurable business outcomes.

• Collaborate with Product Development and engineering leadership on early-stage product definition, solution exploration, and trade-off analysis.

• Represent Product Strategy in executive discussions, strategic customer engagements, and key account meetings, acting as a trusted advisor to the CEO and leadership team.

• Partner effectively with Sales, Marketing, and Customer Success leadership to ensure cohesive go-to-market strategies aligned with product vision.

📝 Enhancement Note: The primary responsibilities highlight a crucial intersection between strategic vision, customer advocacy, and cross-functional leadership. Responsibilities are geared towards influencing product direction through research, market analysis, and strategic prioritization, rather than direct management of development cycles. The emphasis on "doing the work" – writing docs, running interviews, building frameworks – suggests a hands-on leadership approach.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's or Master's degree in a relevant field such as Business, Computer Science, Marketing, or a related discipline is typically expected for VP-level roles.

Experience: 8+ years in product leadership roles, with significant exposure to customer-facing, research-heavy, or strategy-oriented work.

Required Skills:

• Proven experience in product discovery and customer research, including structuring and leading these initiatives.

• Demonstrated success in shaping product strategy within a B2B SaaS environment.

• Ability to engage in detailed product discussions, navigating complex trade-offs between customer value, business priorities, user experience, and technical realities.

• Experience working with products that have significant technical complexity or legacy constraints, understanding the implications for prioritization.

• Strong understanding of product metrics, analytics, and outcome-driven product thinking.

• Excellent communication, presentation, and stakeholder management skills.

• Collaborative mindset with proven influencing skills, capable of leading through relationships and strategic alignment rather than direct authority.

• Comfort and experience operating across distributed teams and varying time zones.

Preferred Skills:

• Familiarity with the HR tech, talent acquisition, or workforce assessment markets.

• Experience working with or alongside distributed engineering teams.

• Familiarity with agile product development methodologies and environments.

• Experience introducing or scaling AI-driven product capabilities.

📝 Enhancement Note: The qualifications emphasize hands-on experience in product strategy and discovery, particularly within B2B SaaS. The requirement for "doing the work" directly in customer research and strategy formulation is a key differentiator. Experience with technical complexity and distributed teams is also critical, signaling the need for a pragmatic and adaptable leader.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Evidence of structured customer research methodologies and synthesized insights that led to strategic product decisions.

• Case studies demonstrating successful product strategy development, roadmap prioritization, and measurable business impact.

• Examples of frameworks or processes developed for outcome-driven product thinking and success measurement.

• Documentation showcasing collaboration with engineering and product development on complex product definitions and trade-offs.

Process Documentation:

• Showcase the candidate's ability to document and communicate complex product strategies and roadmaps clearly for distributed teams.

• Demonstrate experience in defining and communicating product requirements, including trade-offs, to engineering and development teams.

• Provide examples of how metrics and analytics were used to inform product decisions and measure success, linked to specific product initiatives.

📝 Enhancement Note: While a formal portfolio isn't explicitly requested, the job description strongly implies the need for candidates to demonstrate their strategic thinking, research capabilities, and decision-making processes through their experience. Candidates should be prepared to articulate specific examples of their work in strategy, discovery, prioritization, and cross-functional collaboration, effectively presenting a "portfolio of impact" through their interview responses and discussions.

💵 Compensation & Benefits

Salary Range: The compensation package is described as competitive for senior leadership. The base salary is targeted up to $200,000 USD per year, with additional equity. The final compensation will be calibrated based on the candidate's seniority and category authority.

Benefits:

• Comprehensive Health Insurance Plan with $0 deductible and $0 co-pay.

• Dental and Vision Insurance Plans.

• Flexible Spending Account (FSA) option.

• Open Paid Time Off (PTO) Policy.

• 9 Paid Holidays per year.

• Participation in a 401(k) savings plan.

• Company-paid Life and Accidental Death & Dismemberment (AD&D) coverage.

• Equity in the company.

Working Hours: The role is full-time, typically implying a standard 40-hour work week. However, the position requires flexibility to operate across distributed teams and time zones, which may necessitate occasional adjustments to working hours.

📝 Enhancement Note: The salary range is explicitly stated as up to $200,000 USD base plus equity, reflecting a senior executive compensation structure. The benefits package is robust, with a notable emphasis on health coverage ($0 deductible/co-pay) and a flexible PTO policy, common in growth-stage tech companies. The mention of equity is significant for a VP-level role, indicating an opportunity for substantial long-term financial reward tied to company success.

🎯 Team & Company Context

🏢 Company Culture

Industry: B2B SaaS, specifically within the HR Technology (HR Tech) and Talent Acquisition sectors, focusing on pre-hire assessment platforms. The market is described as crowded with point solutions, indicating a competitive landscape where differentiation and strategic positioning are key.

Company Size: Approximately 50 employees total, with a Product and Engineering organization of around 20+ individuals. This size suggests a dynamic, growth-stage environment where individual contributions have a significant and visible impact.

Founded: While the founding date is not provided, the company is described as a B2B SaaS company that has established both an engineering presence in Poland and a leadership hub in San Antonio. This indicates a mature operational setup with a global, distributed workforce.

Team Structure:

• The Product and Engineering organization is based in Poland, comprising over 20 individuals who are growing in maturity and accelerating in velocity, with an increasing embedding of AI into their development process.

• The leadership hub is in San Antonio, where this VP of Product Strategy role is based.

Methodology:

• The company is focused on making strategic bets to scale and differentiate in a competitive market.

• There's an emphasis on customer-centricity, data-driven decision-making, and outcome-oriented thinking.

• The product development process is leaning into AI integration to enhance capabilities and efficiency.

• Strategic clarity and pragmatic execution are core to their approach.

Company Website: eskill.com

📝 Enhancement Note: The company culture is characterized by a blend of strategic vision and pragmatic execution, with a strong emphasis on customer research and data-driven decision-making. The distributed team structure (Poland for Engineering/Product Development, San Antonio for Leadership) necessitates strong communication and collaboration skills. The company's size and focus on scaling suggest an environment where strategic thinking can directly influence growth trajectory.

📈 Career & Growth Analysis

Operations Career Level: This role is at the VP level, signifying a senior leadership position responsible for defining and driving the company's product strategy. It's a strategic role focused on market positioning, customer needs, and long-term product vision, distinct from day-to-day operational execution.

Reporting Structure: The VP of Product Strategy will report directly to the CEO and will have a seat at every important executive conversation. This indicates a high level of visibility and influence within the organization.

Operations Impact: The role's impact is significant, directly shaping the company's product direction, market competitiveness, and ultimately, its growth trajectory. By identifying the right customer problems and market opportunities, this role will drive the development of products that meet market demand and contribute to revenue growth. The strategic decisions made will influence the entire product lifecycle and market positioning.

Growth Opportunities:

• Strategic Leadership: Opportunity to significantly influence the product strategy and long-term vision of a growing B2B SaaS company in a competitive market.

• Skill Development: Deepen expertise in product discovery, market analysis, and strategic prioritization within the HR Tech and assessment space, with potential exposure to AI integration.

• Executive Influence: Direct collaboration with the CEO and leadership team, providing a platform for developing executive presence and strategic decision-making skills.

• Impactful Role: A chance to build and scale a critical function within a ~50-person company, where individual contributions have a direct and visible impact on growth.

📝 Enhancement Note: This role offers a high-impact leadership opportunity with direct influence on company strategy. Growth is framed around strategic leadership, deepening domain expertise, and developing executive presence within a dynamic, growth-stage company. The ability to shape the product roadmap and influence market position provides significant career advancement potential.

🌐 Work Environment

Office Type: The role is based in San Antonio, Texas, and is described as an on-site position. This suggests a physical office environment where leadership team members collaborate.

Office Location(s): San Antonio, Texas, United States. This location serves as the leadership hub for the company.

Workspace Context:

• The San Antonio office functions as the company's leadership hub, implying a professional and collaborative workspace conducive to executive-level discussions and strategic planning.

• While specific office amenities are not detailed, a leadership hub typically offers resources for strategic work, meetings, and cross-functional interaction.

• The role requires close collaboration with a distributed engineering and product development team in Poland, necessitating strong remote communication tools and practices within the San Antonio workspace.

Work Schedule: The role is full-time, with an expectation of 40 hours per week. However, given the distributed nature of the team and the senior leadership level, flexibility will be required to accommodate cross-time zone communication and strategic initiatives, potentially involving some work outside standard hours.

📝 Enhancement Note: The on-site requirement in San Antonio suggests a traditional office environment for the leadership team, fostering in-person collaboration. However, the role's success is heavily dependent on effective remote collaboration with the engineering team in Poland, highlighting the need for tools and practices that bridge the physical and virtual workspaces.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a conversation with HR or a hiring manager to assess basic qualifications and cultural fit.

• Hiring Manager/CEO Interview: In-depth discussion focused on product strategy experience, leadership philosophy, customer research methodologies, and strategic vision.

• Cross-functional Interviews: Conversations with key stakeholders (e.g., Director of Product Development, Sales/Marketing leaders) to assess collaboration style, influencing skills, and understanding of business operations.

• Strategic Case Study/Presentation: Candidates may be asked to present a strategic analysis or product vision based on a prompt, demonstrating their thinking process, research approach, and communication skills. This would serve as a de facto portfolio review.

• Final Round: Likely with the CEO to finalize fit and discuss compensation.

Portfolio Review Tips:

• Focus on Strategic Impact: Highlight examples where your strategic thinking and research led to significant product improvements, market differentiation, or business growth.

• Demonstrate Discovery Process: Be prepared to walk through your methodology for customer interviews, user research, and synthesizing insights.

• Showcase Prioritization Frameworks: Explain how you've made tough prioritization calls, balancing customer value, business goals, and technical constraints.

• Quantify Outcomes: Whenever possible, use metrics and data to demonstrate the impact of your strategic decisions on product success and business outcomes.

• Address Distributed Collaboration: Be ready to discuss how you've effectively collaborated with and influenced remote teams.

Challenge Preparation:

• Strategic Analysis: Prepare to analyze a market landscape or a product challenge, proposing strategic solutions and a roadmap.

• Customer Problem Framing: Practice framing customer problems and articulating potential solutions based on research and strategic objectives.

• Trade-off Discussions: Be ready to discuss complex trade-offs in product development (e.g., feature scope vs. time-to-market, user experience vs. technical feasibility) and how you approach them.

📝 Enhancement Note: The interview process will likely involve a strong emphasis on strategic thinking, customer empathy, and leadership influence. Candidates should prepare to articulate their strategic methodology, demonstrate their research capabilities, and showcase how they translate insights into actionable plans. A "portfolio" of impact will be assessed through detailed examples and potentially a strategic presentation.

🛠 Tools & Technology Stack

Primary Tools:

• Product Management Platforms: Tools for roadmap planning, backlog management, and feature prioritization (e.g., Jira, Aha!, Productboard).

• Customer Research & Feedback Tools: Platforms for conducting interviews, surveys, and gathering user feedback (e.g., UserTesting.com, SurveyMonkey, Typeform, tools for managing customer insights).

• Analytics & Business Intelligence Tools: Software for analyzing product usage, customer behavior, and business metrics (e.g., Google Analytics, Mixpanel, Amplitude, Tableau, Power BI).

• Collaboration & Communication Tools: Essential for working with distributed teams (e.g., Slack, Microsoft Teams, Zoom, Confluence, Google Workspace).

• CRM Systems: Understanding of how CRM data (e.g., Salesforce) informs product strategy and customer segmentation.

Analytics & Reporting:

• Proficiency in defining KPIs and OKRs for product success.

• Ability to interpret data from various sources to inform strategic decisions.

CRM & Automation:

• While not a direct CRM management role, understanding how CRM data influences product strategy and customer segmentation is crucial.

• Awareness of how product automation features can drive business value and customer adoption.

📝 Enhancement Note: While specific tools aren't listed, the role implies a need for proficiency in standard product management, analytics, and collaboration tools. A strong understanding of how data from CRM, analytics platforms, and customer feedback tools informs strategic product decisions and roadmap prioritization is essential. Familiarity with AI integration tools may also be beneficial given the company's direction.

👥 Team Culture & Values

Operations Values:

• Customer Centricity: Deeply understanding and prioritizing customer needs and problems as the foundation for product strategy.

• Strategic Clarity: Bringing clear, well-reasoned direction to product development, ensuring alignment across the organization.

• Data-Driven Decision Making: Utilizing metrics and analytics to inform strategic choices and measure product impact.

• Pragmatic Execution: Balancing visionary strategy with a realistic understanding of implementation constraints and operational realities.

• Collaboration & Influence: Fostering strong working relationships and influencing stakeholders across distributed teams to achieve common goals.

• Growth Mindset: Embracing continuous learning, market adaptation, and the integration of new technologies like AI.

Collaboration Style:

• Cross-functional Partnership: Working closely with CEO, Product Development, Engineering, Sales, Marketing, and Customer Success to ensure cohesive strategy and execution.

• Influence and Alignment: Leading through relationships, clear communication, and data-backed recommendations to gain buy-in and alignment, especially across geographically dispersed teams.

• Feedback Integration: Openness to feedback and iterative refinement of strategy based on input from various departments and market signals.

• Knowledge Sharing: Actively sharing insights from customer research and market analysis to empower the broader product and engineering organization.

📝 Enhancement Note: The company values emphasize a balance between strategic thinking and execution, deeply rooted in customer understanding and data. The collaboration style is critical for success, requiring strong influencing skills to align a distributed team and effectively partner with various departments.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Strategy and Execution: Bridging the gap between high-level product strategy and the practical realities of software development, especially with a distributed engineering team.

• Market Saturation: Navigating a crowded pre-hire assessment market and defining a clear, differentiated product strategy.

• Influence Without Authority: Effectively driving product direction and priorities through influence rather than direct management of the engineering team.

• Distributed Team Dynamics: Ensuring seamless communication, alignment, and collaboration across different time zones and cultures.

• AI Integration Strategy: Developing a cohesive strategy for integrating AI capabilities effectively into the product offering.

Learning & Development Opportunities:

• Strategic Impact: Direct involvement in shaping the core product strategy of a scaling B2B SaaS company.

• Domain Expertise: Deepen knowledge within the HR Tech, talent acquisition, and assessment markets.

• Executive Leadership: Develop strategic leadership skills through close work with the CEO and executive team.

• AI Product Development: Gain experience in formulating strategy for AI-driven product features.

• Cross-cultural Collaboration: Enhance skills in managing and influencing teams across different geographic locations and time zones.

📝 Enhancement Note: The primary challenges revolve around strategic leadership in a complex, competitive market with a distributed team structure. Growth opportunities are significant, centered on shaping company direction, deepening domain expertise, and developing executive-level strategic capabilities.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you identified a significant customer problem through research and how that insight shaped your product strategy." (Focus on methodology, impact, and decision-making)

• "How would you prioritize competing product roadmap initiatives in a B2B SaaS environment, considering customer value, technical feasibility, and business goals?" (Prepare to discuss frameworks and trade-offs)

• "Imagine our current pre-hire assessment platform needs to evolve to incorporate AI. What would be your first steps in developing a product strategy for this?" (Demonstrate strategic thinking, market awareness, and process)

Company & Culture Questions:

• "What excites you about eSkill's mission and our approach to pre-hire assessments?" (Research the company, its product, and its market position)

• "How do you foster collaboration and influence across different departments (Sales, Marketing, CS, Engineering) when you don't have direct authority?" (Prepare examples of cross-functional leadership)

Portfolio Presentation Strategy:

• Structure Your Narrative: For any case studies or examples, follow a clear structure: Problem -> Your Role/Approach -> Solution/Strategy -> Outcome/Impact (quantified if possible).

• Highlight Strategic Thinking: Emphasize the "why" behind your decisions, showing your analytical process and strategic rationale.

• Showcase Research Rigor: Detail your methods for customer discovery and how insights were translated into actionable product direction.

• Demonstrate Pragmatism: Be ready to discuss how you handled constraints, trade-offs, and technical complexities.

• Focus on Influence: Explain how you gained buy-in and aligned stakeholders with your strategic vision.

📝 Enhancement Note: Interview preparation should focus on articulating a clear strategic methodology, demonstrating deep customer empathy, and showcasing an ability to influence diverse teams. Candidates should be ready to discuss their process for product discovery, roadmap prioritization, and strategic decision-making, using concrete examples that highlight their impact.

📌 Application Steps

To apply for this VP of Product Strategy position:

• Submit your application through the provided Workable link.

• Customize Your Resume: Tailor your resume to highlight 8+ years of product leadership experience, with specific emphasis on B2B SaaS strategy, customer research, product discovery, and influencing distributed teams. Use keywords from the job description.

• Prepare Your "Portfolio of Impact": Be ready to articulate specific examples of your strategic contributions, customer research initiatives, roadmap development, and how you've driven measurable business outcomes. Think of your interview responses as your portfolio.

• Research eSkill: Thoroughly understand eSkill's product, target market (HR Tech, talent acquisition), competitive landscape, and company mission. Prepare to discuss how your vision aligns with their goals.

• Practice Strategic Communication: Rehearse articulating your product strategy, research findings, and decision-making process clearly and concisely, as you will likely be asked to present or discuss case studies.

⚠️ 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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