Head of Product - TestAssure

TestAssure

$130K — $160K *
Consumer Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5-8 years of product management experience, ideally in WFM or HR tech.
  • Customer-focused with a strong emphasis on discovery and validation.
  • Ability to balance user experience improvements with technical feasibility.
  • Proven track record of working autonomously and aligning cross-functions.
  • Familiarity with Agile methodologies and strong specification writing skills.
  • Attention to detail, capable of wireframing user flows effectively.
  • Enthusiastic about working in a high-growth, ownership-driven environment.

Responsibilities

  • Develop and manage the product vision and roadmap aligned with business strategy.
  • Enhance user experience and drive product engagement through continuous improvement.
  • Collaborate with engineering and design teams to deliver high-quality features.
  • Advance reporting capabilities for better product utility for admins and managers.
  • Identify opportunities to embed AI for productivity enhancements.
  • Maintain technical fluency to engage deeply in discussions about the tech stack and architecture.
  • Conduct direct customer engagement to gather feedback and validate product decisions.
  • Provide clarity in the product development process by making decisive, bold choices.

Benefits

  • High-autonomy, high-impact role with meaningful ownership.
  • Opportunity to build and scale a product addressing real user needs.
  • Supportive leadership team empowering you to take product lead.
  • Collaborative culture with low egos, offering remote work flexibility (US and CA).
  • Health insurance and 401(k) with employee matching contributions.
Full Job Description
We9re looking for a strategic, technically fluent Head of Product to take ownership of our product vision, roadmap, and execution. You will work directly with a product focused CTO and engineering team to shape and scale our product offering. You will be key to completing the discovery phase of product development engaging directly with customers and ensuring delivery of high value features. You9ll be a high-trust individual empowered to make decisions and own the product direction, with two direct reports.

About the Role

This role is ideal for someone who thrives in early-growth environments, understands the nuances of workforce management, and is comfortable navigating trade-offs, tech debt, and user complexity. You will be expected to set direction, say 4no4 when needed, and focus the company around a cohesive product strategy.

Responsibilities
  • Develop and own the product vision, roadmap, and execution plan aligned to business strategy using data-informed decision making.
  • Improve the user experience, reduce complexity, and drive higher product engagement.
  • Collaborate with engineers and designers to scope, spec, and ship high-quality features.
  • Lead the evolution of reporting capabilities to increase product utility for admins and managers.
  • Proactively evaluate where and how AI can be embedded in the product to create measurable productivity gains.
  • Maintain technical fluency - understand the SDLC, tech stack, APIs, and architectural trade-offs (you don9t need to code, but you need to engage deeply).
  • Talk directly to customers (payroll admins, test consultants, project managers) to gather insights and validate decisions.
  • Bring clarity and focus to the product development process - making bold choices, even when it means closing doors.


Success in This Role Looks Like:
  • We deliver better product - with improved UX, tighter integrations, improved reporting, and upsell opportunities.
  • We see measurably deeper engagement with our product across user roles.
  • You establish a product strategy we can rally behind and execute on.

Requirements
    • Have a minimum of 5-8 years of product management experience. Exposure to WFM, HR tech, time & attendance, or scheduling platforms is a nice-to-have.
    • Are deeply customer-focused and comfortable owning customer discovery and validation.
    • Know how to balance UX improvements, technical architecture, and feature delivery.
    • Can work autonomously and drive cross-functional alignment with minimal oversight.
    • Understand Agile, can write clear specs, and know how to work with engineers to get things built.
    • Have an eye for detail and can wireframe user flows to communicate product ideas.
    • Are excited to be part of a high-ownership, fast-growth company where product will shape the future.

Benefits
    • High-autonomy, high-impact role with meaningful ownership.
    • A chance to build and scale a product that solves real pain-points for real users.
    • Supportive leadership team that9s ready to let you lead on product.
    • Low egos, PE-backed, remote team (US and CA), health insurance, 401(k) employee match.
    • Competitive compensation - Remuneration and title will be determined commensurate with experience.

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