Principal Product Designer

Description

Location:  Hybrid to Wayne or Naperville

How you'll contribute to our mission

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.

How you'll drive success

• 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, accessibility, 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-consuming 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 design intent, navigate tradeoffs, and ensure the quality of the shipped experience.
• Connect design decisions to measurable customer and business outcomes, using qualitative insight, product data, experimentation, and feedback to understand impact and guide iteration.
• Influence senior and executive stakeholders through clear storytelling, prototypes, evidence, and a strong point of view while remaining open to challenge and new information.
• Mentor and elevate other designers through critique, coaching, shared practices, and the standard set by your own work.
• Identify opportunities where experience innovation can differentiate Frontline in the market and strengthen adoption, customer trust, and long-term value.
• Take ownership of high-impact design challenges from ambiguity through outcome, while bringing Product, Engineering, Research, and other partners together to make the result stronger.

What you bring to help us grow

• 10+ years of experience designing digital products, with recognized expertise in product design, experience strategy, and customer-centered problem solving.
• A portfolio demonstrating leadership of large-scale, complex product experiences and measurable customer or business impact.
• Deep experience designing complex SaaS, enterprise, platform, or similarly sophisticated digital products.
• Demonstrated ability to define experience vision and translate that vision into products and workflows customers can successfully use.
• Exceptional interaction, visual, information architecture, prototyping, and systems design capabilities.
• Strong proficiency with Figma and modern design and prototyping tools.
• Experience leading discovery and using customer research, behavioral data, experimentation, and feedback to shape product direction.
• Demonstrated ability to simplify interconnected workflows and complex systems without losing important customer or business context.
• Experience contributing to or shaping scalable design systems, shared patterns, and experience standards.
• Strong understanding of accessibility and inclusive design, including practical application of WCAG principles.
• Experience influencing product strategy and senior stakeholders through design expertise, evidence, storytelling, and facilitation.
• Ability to connect design decisions to customer success, product differentiation, adoption, and broader business outcomes.
• Experience mentoring designers and raising design quality through constructive critique and shared learning.
• Curiosity and practical experience with AI-assisted design tools and emerging AI interaction patterns, with the judgment to evaluate where AI adds meaningful value and where it does not.
• Experience with K-12 education, EdTech, or products serving complex professional workflows is valuable but not required.

What you'll need to thrive

You’ll thrive here if you are comfortable owning consequential problems without waiting for every detail to be defined. You bring structure to ambiguity, follow through on commitments, and stay close enough to the work to understand whether the experience we intended is the experience customers actually receive.

You build trust by listening closely to customers and colleagues, challenging assumptions thoughtfully, and making decisions with the people who use our products in mind. You care about solving the underlying problem, not simply delivering what was initially requested.

You believe the strongest products come from teams working together. You invite different perspectives, share what you know, help others grow, and can influence across Product, Engineering, Research, and leadership without relying on authority.

You are also an active learner. You experiment with emerging tools and approaches, including AI, while applying judgment to their use. You are comfortable questioning established patterns when a better solution is possible and equally comfortable recognizing when simplicity is the better innovation.

Above all, you care about creating technology that respects educators’ time, earns their trust, and helps schools focus more energy on the people and outcomes that matter most.

Our Mission, Our People, Our Purpose

At Frontline Education, we’re reimagining what’s possible by becoming an AI-first organization, transforming how we think, work, and serve the educators who shape our schools every day. By using AI in thoughtful, practical ways, we’re creating tools that help educators save time, gain insights, and focus more on what matters most — their students.

As part of our team, you’ll be expected and empowered to build and apply AI skillsets that grow with you, because at Frontline Education, technology amplifies what matters most: the human drive to learn, improve, and make a difference.

How We Support Growth, Balance, and Well-Being
• Personalized Time Off: Take time when it’s needed most — whether that’s a family vacation, a reset day, or simply time to rest and refocus.
• Paid Sick Time: Separate, dedicated sick leave to care for yourself or loved ones.
• Volunteer Time Off: Paid time to give back and support causes that matter to you.
• Ten Paid Holidays: Enjoy meaningful moments and traditions throughout the year.
• Our Philosophy: We believe time away from work helps you bring your best self to it.

Continuous Learning and Growth
• World-Class Learning Access: Explore thousands of on-demand courses through platforms like LinkedIn Learning.
• Leadership & Technical Skill Building: Develop new capabilities and chart your own professional path.
• AI Empowerment: Use OpenAI tools to build fluency with emerging technology and harness AI as a creative partner for innovation and problem-solving.
• Tuition Reimbursement: Invest in formal education to advance your skills and career.
• Ongoing Learning Culture: Participate in company-led webinars on AI, inclusion, and industry trends—designed to inspire curiosity and continuous improvement.

Health, Happiness, and Purpose
• Wellness Initiatives: Company-sponsored programs that support physical, mental, and emotional well-being.
• Employee Assistance Program (EAP): Confidential support for you and your family’s needs.
• Comprehensive Benefits: Health and financial benefits that support your happiness and future.
• A Culture That Cares: At Frontline Education, we want every team member to learn, grow, and thrive—personally, professionally, and purposefully.

Compensation & Benefits

This role is eligible for Frontline’s comprehensive benefits package, including bonus eligibility, 401(k) match, Employee Stock Purchase Plan, comprehensive health benefits, personalized time off, paid sick time, and tuition reimbursement for eligible coursework.

The full base salary range for this position is between $160,000 and $180,000. 

Inclusion, Belonging & Equal Opportunity

Frontline Education is an equal opportunity/affirmative action employer. We aspire to have an inclusive workplace and strongly encourage suitably qualified applicants from a wide range of backgrounds to apply and join our team.

Interview Process & Data Privacy

As part of our interview process, Frontline uses video conferencing tools that include photo capture and may include automated transcription features. A screenshot or photo will be taken at the start of the interview for internal identification and record-keeping purposes only, and transcription may be used to support notetaking and evaluation consistency. These materials are used solely by our recruiting and hiring teams, stored securely, and not shared outside the hiring process. Candidates may opt out of the transcription at any time by notifying their recruiter in advance. Frontline processes this information in accordance with applicable data privacy laws and only for legitimate business purposes related to recruitment and hiring.

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