VP of Product Strategy

eSkill•San Antonio, TX

1d•$0 - $200,000•Hybrid

About The Position

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.

Requirements

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 Haves

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

Responsibilities

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
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
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
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
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
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