
VP of Product Strategy
At a glance
Highlights
- executive seat at CEO discussions
- direct impact on company growth
- competitive senior compensation
- equity participation
Heads up
- no direct engineering management
- hands-on product work required
Why this role might suit you
An experienced product leader can shape strategy for a growing B2B SaaS company, influence executive decisions, and drive customer‑centric innovation while enjoying competitive compensation, equity, and a hands‑on role with visible impact on the organization’s trajectory.
Skills
About the 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.
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 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.
Benefits
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
Compensation
This Product Manager role pays $200k/yr. Within typical range for product manager roles in United States.
Questions about this role
How do I apply to this VP of Product Strategy role at eSkill?
Click "Apply with AI Applyd" above. We auto-fill the application from your resume and answer screening questions in seconds. No copy and paste, no juggling tabs.
What's the typical salary for Product Manager in United States?
Compensation for Product Manager roles in United States varies widely by seniority, employer size, and remote vs onsite arrangement. Check the salary range on this listing when published, or browse our Product Manager hub for United States medians across recent openings.
How fast does AI Applyd auto-apply?
Most applications complete in under 90 seconds. You can track the status in your dashboard and watch the screenshot proof land the moment the application submits.
What ATS does eSkill use?
AI Applyd supports Greenhouse, Lever, Ashby, Workday, iCIMS, SmartRecruiters, LinkedIn Easy Apply, and most other ATS platforms. If we can submit through the platform, we do.
Want AI Applyd to auto-apply to roles like this?
We tailor your resume per posting, fill the forms, and track replies for you.