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Director of Product Design

About ParentSquare

ParentSquare is the leading school-home communication platform, serving over 20 million student families nationwide. We empower schools to engage families effectively, creating stronger communities that support student success. As we continue our rapid growth, we’re looking for a Director of Product Design to lead and elevate our design strategy.


About the Role

We’re looking for a Director of Product Design to lead our talented team of 7 designers and drive the evolution of ParentSquare’s user experience. Our product has grown rapidly with new features, but the core design has not been fully reimagined in years. This role requires someone who can lead a team to iteratively improve an existing product while scaling a design system for the future.

You will work closely with our Founder, CPO, Product, and Engineering teams ensuring we maintain our high retention and NPS while expanding our footprint. If you thrive in a fast-growth, iterative environment and are passionate about making a real impact in K-12 education, we’d love to hear from you!


What You’ll Do

  • Lead & Scale the Design Team – Mentor and manage a team of 7 designers, fostering a collaborative, user-centered approach.
  • Drive Product UX Strategy – Partner with Product and Engineering to improve UX iteratively while maintaining development speed.
  • Establish & Scale a Design System – Build, refine, and scale our design system to ensure consistency and efficiency.
  • Be Hands-On When Needed – While leading the team, be ready to jump in and contribute directly to design work where needed.
  • Ensure Frugality & Speed – Deliver high-quality design work without unnecessary complexity or cost.
  • Collaborate Cross-Functionally – Work with Product Managers, Engineers, and Leadership to align on vision and execution.
  • Improve Key Business Metrics – Focus on driving ARR, retention, and NPS through exceptional user experience.

What We’re Looking For

  • 8+ years of experience in Product Design, with 3+ years leading teams.
  • Experience designing for B2B SaaS or EdTech products.
  • Proven success improving legacy products through iterative design.
  • Deep understanding of accessibility, visual design, and understanding user workflows.
  • Experience building and scaling a design system.
  • Ability to balance fast execution with thoughtful design.
  • Strong cross-functional collaboration skills—comfortable working with Founders, CPO, Product, and Engineering teams.
  • Passion for helping schools and educators succeed.

Why Join Us?

At ParentSquare, we believe in winning together and building a product that truly serves schools, educators, and families. We value transparency, collaboration, and an entrepreneurial spirit, and we look for team members who share these values. You’ll have the opportunity to lead design at scale, influence a fast-growing company, and make a meaningful impact on K-12 education.

The perks of working for us are great! You’ll get your foot in the door as our company continues to grow. We’re big believers in work-life balance and provide:

  • Employer-paid health insurance (including dependent coverage)
  • An employer-matched 401K retirement savings program from day 1 
  • Paid Parental Leave
  • Stock options
  • Health + wellness reimbursements
  • Generous PTO 
  • 15 paid holidays, including your birthday! 

As a fully remote team, we’ll make sure you have all the tools and equipment you need to make your home office a place where you can thrive. 

We're an equal-opportunity employer. All applicants will be considered for employment without attention to age, race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.

The salary range for this role will be $175 ,000 - $200,000 DOE. 

Average salary estimate

$187500 / YEARLY (est.)
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$175000K
$200000K

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What You Should Know About Director of Product Design, ParentSquare

At ParentSquare, we are on a mission to enhance school-home communication, serving over 20 million families across the nation. We are seeking a talented Director of Product Design to join our fully remote team and lead the charge in redefining our user experience. As the Director of Product Design, you will guide a team of seven creative designers, mentoring them while fostering a collaborative and user-focused environment. Your role will be pivotal, as you work closely with our Founder, CPO, and product and engineering teams to iterate on our existing product and establish a robust design system for future scalability. If you thrive in a fast-growth, innovative environment and are excited about making a real impact in K-12 education, you’ve found the right place. We need you to help improve key business metrics through exceptional user experiences, ensuring that we maintain high retention rates and a positive Net Promoter Score (NPS). In this position, you'll find opportunities to be hands-on with design projects when necessary, while also driving a strategic vision that aligns across different disciplines. If shaping the design landscape in the education technology space excites you, we can’t wait to hear from you and see how your expertise can transform ParentSquare's future.

Frequently Asked Questions (FAQs) for Director of Product Design Role at ParentSquare
What are the responsibilities of a Director of Product Design at ParentSquare?

The Director of Product Design at ParentSquare is tasked with leading and scaling a design team while ensuring a user-centered design approach. This role involves driving product UX strategy in collaboration with product and engineering teams, establishing a scalable design system, improving key business metrics, and mentoring a talented group of designers.

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What qualifications are required for the Director of Product Design position at ParentSquare?

Candidates for the Director of Product Design position at ParentSquare should have 8+ years of experience in product design, including at least 3 years in a leadership role. Additionally, applicants should have experience in designing for B2B SaaS or EdTech products, a proven track record in improving legacy products, and strong collaboration skills.

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How important is team collaboration for the Director of Product Design at ParentSquare?

Collaboration is essential for the Director of Product Design role at ParentSquare. The successful candidate will regularly engage with cross-functional teams, including product managers, engineers, and leadership, to align on strategic vision and execution, ensuring that design effectively meets business goals.

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What are some key metrics the Director of Product Design at ParentSquare will focus on?

In the Director of Product Design role at ParentSquare, the focus will be on improving key business metrics such as Annual Recurring Revenue (ARR), customer retention, and Net Promoter Score (NPS). These metrics reflect the success of enhancing the user experience and achieving company goals.

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What type of work culture can a Director of Product Design expect at ParentSquare?

ParentSquare promotes a culture of transparency, collaboration, and entrepreneurial spirit. As a Director of Product Design, you’ll experience a supportive environment that values work-life balance, encouraging team members to thrive while pursuing meaningful impacts on K-12 education.

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Common Interview Questions for Director of Product Design
How do you approach leading a design team as the Director of Product Design?

When leading a design team, it's crucial to foster a user-centered culture and encourage collaboration. Establish regular check-ins, promote open communication, and mentor your team members to create an environment where innovative ideas can flourish.

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Can you describe your experience with establishing a design system?

In your response, detail the steps you took to build a design system, including identifying key components, defining usage guidelines, and collaborating with cross-functional teams to ensure alignment and adoption across products.

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How do you balance speed and quality in design work?

Balancing speed and quality in design requires clear priorities, iterative testing, and responsiveness to user feedback. Emphasize the importance of quick prototyping and validating assumptions to maintain development timelines without compromising quality.

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What strategies would you use to improve user experience for a legacy product?

Start by gathering user feedback through surveys or interviews, then identify pain points and opportunities for improvement. Using an iterative design process, propose changes and test them with users to ensure they effectively address issues.

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How do you ensure accessibility in your design work?

Discuss your approach to accessibility, such as adhering to WCAG guidelines, conducting accessibility audits, and involving users with disabilities in the design process to gather insights and validate accessible designs.

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What is your experience with B2B SaaS product design?

Share specific examples of previous B2B SaaS products you've designed, highlighting unique challenges and solutions tailored to business users' needs, focusing on enhancing usability and functionality.

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How do you handle feedback from non-design stakeholders?

It's important to listen actively and understand the perspective of non-design stakeholders. Respond constructively, offering clarity on design decisions while remaining open to incorporating valuable suggestions that align with user needs.

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Can you give an example of a design project that made a significant impact?

Describe a specific project where your design work led to measurable improvements, such as increased user engagement, retention rates, or customer satisfaction, and explain the process you followed to achieve these outcomes.

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What tools do you prefer for design and collaboration?

Mention industry-standard tools such as Sketch, Figma, Adobe XD, along with project management and collaboration tools like Asana or Trello. Emphasize how these tools facilitate effective design workflows and teamwork.

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What is your vision for the future of product design in educational technology?

Share insights on trends shaping the future of educational technology, emphasizing user-centered design principles, accessibility, and the potential of design to improve learning outcomes, thereby demonstrating your commitment to this mission.

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The idea for ParentSquare was born in 2010 when Anu, a computer engineer, who had recently taken a sabbatical from work to be with her young school-age kids, experienced the difference in how connected she was with her kids’ life at school being a...

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DATE POSTED
April 6, 2025

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