Head of Product - TestAssure

TestAssure is a fast-moving software company providing best-in-class automated testing solutions of workforce management rules. Our product services many of the world’s leading businesses and provides our customers highly quantifiable value, but it’s only just beginning. We’re looking to evolve our platform, improve UX, extend integrations, unlock new growth and ultimately deliver more value to customers.

We’re 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. You’ll 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 “no” 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 don’t 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 that’s 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.