Principal Product Designer

Location:

Hybrid to Wayne or Naperville

At Frontline Education, we transform how schools work, so every educator and student succeeds. Our vision is simple and ambitious: every school thriving. Every community stronger.

As a Principal Product Designer, you'll help turn that purpose into experiences that make a meaningful difference in the daily work of educators and administrators. You'll be one of our most senior individual contributors in Product Design, leading large-scale design initiatives across Frontline's product portfolio and helping define what exceptional, connected experiences look like for the schools and communities we serve.

You'll work at the intersection of customer insight, product strategy, technology, and design craft. Rather than starting with requests or features, you'll help teams deeply understand the problems that matter most to customers, frame the right opportunities, and create experiences that deliver measurable customer and business outcomes.

You'll partner closely with Product Management, Engineering, Research, and leaders across Frontline to establish long-term experience direction, simplify complex workflows, and create greater cohesion across our product ecosystem. You'll also help shape how AI changes the experiences we create and the way our design organization works, balancing innovation with transparency, accessibility, trust, and human judgment.

This is a hands‑on leadership role for someone who can move comfortably between long‑term vision and detailed execution, bring people together around complex problems, and raise the quality of design through both their work and their influence.

• Define and champion long-term experience vision and design strategy across Frontline’s product portfolio, connecting customer needs, product strategy, technology, and business outcomes.
• Lead some of Frontline's most complex and ambiguous design initiatives, creating clarity where the path forward is not yet defined and guiding work from discovery through delivery and continuous improvement.
• Partner deeply with customers and research teams to understand educators' and administrators' workflows, goals, constraints, and unmet needs, ensuring decisions reflect what will create meaningful outcomes rather than simply responding to individual requests.
• Operate as a strategic partner to Product and Engineering leaders, influencing priorities and investment decisions through customer insight, evidence, systems thinking, and compelling design direction.
• Design cohesive end-to-end experiences across products and workflows, identifying opportunities to simplify complexity and make Frontline's broader platform feel increasingly connected and intuitive.
• Establish and raise standards for interaction design, visual design, systems thinking, accessibility, prototyping, and overall experience quality.
• Advance Frontline's design system and shared experience patterns, helping teams create consistent, accessible, scalable experiences while leaving room for thoughtful product innovation.
• Define thoughtful approaches for AI-enabled and adaptive experiences, considering user control, transparency, trust, and the appropriate role of human judgment.
• Use AI throughout discovery, synthesis, ideation, prototyping, experimentation, and design delivery to increase learning velocity and explore possibilities that would otherwise be difficult or time‑thinking to test.
• Establish effective AI-enabled design practices and share what works across the organization, applying sound judgment to validate outputs and ensuring technology strengthens rather than replaces human‑centered design.
• Work closely with Engineering throughout implementation to preserve…