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VP of Product Strategy

Job in San Antonio, Bexar County, Texas, 78208, USA
Listing for: eSkill
Full Time position
Listed on 2026-06-23
Job specializations:
  • Business
    Product Manager, Business Management & Consulting, Business Analyst
Salary/Wage Range or Industry Benchmark: 200000 - 250000 USD Yearly USD 200000.00 250000.00 YEAR
Job Description & How to Apply Below

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 trade‑offs, 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.

Requirements 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 trade‑offs 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…
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