VP of Product Strategy at eSkill

San Antonio, Texas, United States -

Full Time

Start Date

Immediate

Expiry Date

29 Aug, 26

Salary

200000.0

Posted On

31 May, 26

Experience

10 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Product Strategy, Customer Research, Product Discovery, B2B SaaS, Roadmap Prioritization, Market Intelligence, Product Analytics, Stakeholder Management, Cross-functional Collaboration, Business Analysis, Outcome-driven Thinking, Strategic Planning

Industry

Human Resources Services

Description

About the Role We're a B2B SaaS company building the most comprehensive pre-hire assessment platform on the market - combining hard skills assessments, task-based assessments, and behavioral assessments in one place. Our engineering and product development organization is based in Poland, and our leadership hub is in San Antonio. We're looking for a VP of Product Strategy to help us make the right bets as we scale. This role is for someone who thrives in discovery and strategy while staying grounded in practical product realities - someone who enjoys going deep on customer problems, shaping solutions collaboratively, and translating insight into clear direction that a strong execution organization can run with. We’re looking for a hands-on leader ready to do the work: writing the docs, running the interviews, building the frameworks, and shaping the thinking - not delegating it down. What You'll Own Customer Research & Discovery Serve as the primary voice of the customer within the product organization Lead customer interviews, discovery initiatives, and feedback programs Synthesize customer insights into actionable product recommendations and strategic direction Product Strategy & Roadmap Direction Define roadmap priorities and long-term product direction in partnership with the CEO and Director of Product Development Connect customer insight, market opportunities, and business goals into clear product recommendations Drive confident prioritization decisions grounded in both customer value and business impact Business Analysis & Market Intelligence Monitor market trends, competitor landscape, and emerging opportunities in the pre-hire assessment space Evaluate and communicate strategic product opportunities and risks Bring structure and clarity to product decision-making processes Product Metrics & Analytics Define frameworks for measuring product success and business outcomes Ensure decisions are informed by meaningful metrics and customer impact Build stronger outcome-oriented thinking across the product organization Product Definition & Cross-Functional Collaboration Partner closely with the Director of Product Development and engineering leadership during early product definition and solution exploration Participate in shaping product requirements, evaluating tradeoffs, and aligning customer needs with implementation realities Collaborate on complex product decisions where business goals, user experience, and technical constraints intersect Ensure strategic direction is properly sequenced, actionable, and executable across a distributed team Executive & Customer-Facing Leadership Represent Product in executive discussions, strategic customer conversations, and key account meetings Partner with Sales, Marketing, and Customer Success leadership Act as a trusted strategic partner to the CEO and leadership team What This Role Is Not This role does not directly manage day-to-day engineering execution, sprint delivery, or development operations. Those functions are owned by an established Product Development and Engineering organization in Poland. But this is equally not a high-altitude strategy role disconnected from how the product actually gets built. We need someone who engages seriously with product complexity, understands technical and operational constraints, and works closely with Product Development to make pragmatic decisions - not someone who hands off a vision document and steps back. Success here comes from influence, collaboration, and strategic clarity - not top-down ownership. What We're Looking For 8+ years in product leadership roles, with significant exposure to customer-facing, research-heavy, or strategy-oriented work Strong product discovery and customer research experience - you've structured and led it, not just participated Experience shaping product strategy in a B2B SaaS environment Comfortable engaging in detailed product discussions and navigating tradeoffs between customer value, business priorities, UX, and technical realities Experience working on products with meaningful technical complexity or legacy constraints - you understand what that means for prioritization Strong understanding of product metrics, analytics, and outcome-driven product thinking Excellent communication and stakeholder management skills Collaborative mindset with strong influencing skills - you lead through relationships, not authority Comfort operating across distributed teams and time zones Strategic thinker with a pragmatic approach to execution realities Nice to Have Familiarity with HR tech, talent acquisition, or workforce assessment markets Experience working with or alongside distributed engineering teams Familiarity with agile product development environments Experience introducing or scaling AI-driven product capabilities Why This Role Pre-hire assessment is a crowded space full of point solutions - platforms that do one thing well. Our bet is that the market wants something different: a single platform that covers every meaningful dimension of candidate evaluation, from cognitive and behavioral assessments to AI simulations and real-world task tests. We have the content library, the breadth of assessment types, and the engineering team to get there. With roughly 20+ people in the Product and Engineering organization - a team that's growing in maturity and accelerating in velocity as we embed AI into our development process - what we're building now is the strategic layer to make sure we get there in the right order, for the right customers, with the right bets. You'll work directly with the CEO, have a seat at every important conversation, and own the part of product work that's often hardest to do well: understanding customers and markets deeply enough to make confident decisions about what to build next - and bringing that clarity to a team that's ready to execute. At roughly 50 people total in the company, this is a role where your thinking will have direct, visible impact on our growth trajectory. Compensation Competitive senior leadership package — base up to $200k, plus equity. We'll calibrate to the seniority and category authority you bring. Benefits Health insurance plan with $0 deductible and $0 co-pay. Dental and vision insurance plans. Flexible spending account option. Open PTO Policy plus 9 paid holidays per year. Participation in our 401(k) savings plan Company-paid Life and AD&D coverage

Responsibilities

Lead customer discovery and research to define the long-term product strategy and roadmap priorities for a B2B SaaS assessment platform. Partner with executive leadership and engineering to translate customer insights into actionable product requirements and measurable business outcomes.