Head Of Product - Testassure - Brydon Portfolio Company - Remote Eligible

Head Of Product

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'll report directly to the CEO, partner tightly with the CTO and our R&D team, and engage directly with customers to shape and scale our product offering. You'll be the first dedicated product hire — a high-trust individual contributor empowered to make decisions and own the product direction.

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

• Define and own the product vision, roadmap, and execution plan in partnership with the executive team.
• 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 how AI can be embedded in the product to create real 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).
• Wireframe product experiences and work closely with design to shape intuitive workflows.
• 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.