VP of Product Strategy

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πŸ“ San Antonio, Texas, United StatesFull time

About this role

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 β€” 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

Frequently Asked Questions

Is the salary disclosed for the VP of Product Strategy position at Eskill?
The salary for this VP of Product Strategy role at Eskill is not publicly listed. Click "Apply Now" to learn more about the compensation package on their official careers page.
Where is the VP of Product Strategy position at Eskill located?
This VP of Product Strategy role at Eskill is based in San Antonio, Texas, United States. The position is listed as on-site or hybrid. Check the full job description or apply directly to confirm the work arrangement.
Is the VP of Product Strategy role at Eskill full-time or part-time?
This is listed as a Full time position. It is posted as a VP of Product Strategy role at Eskill.
How do I apply for the VP of Product Strategy position at Eskill?
Click the "Apply Now" button on this page. You will be redirected to Eskill's official application portal hosted on workable where you can submit your application directly.
When was the VP of Product Strategy job at Eskill posted?
This VP of Product Strategy position at Eskill was posted on May 31, 2026. Apply as soon as possible β€” early applications are often reviewed first.
VP of Product Strategy
Eskill
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