Principal Engineer

ParentSquare is rooted in the belief that when families are involved, students thrive. We're founder-led, started in 2011 by a parent who saw firsthand how much stronger classrooms become when schools and families work together, and making that partnership possible for every family is still our mission today.

As the trusted leader in school-home engagement, we help schools reach the parents and guardians of more than 22 million students in 190+ languages through the channels families prefer, including app, text, email, and phone. Our all-in-one platform brings together communications, attendance, forms, payments, and websites to simplify how schools and families connect and take action. ParentSquare Intelligence, the AI and data layer built into ParentSquare, turns engagement and attendance data into insights that guide proactive outreach, so districts can offer families the right support at the right time. Over 42,000 schools in all 50 states use ParentSquare to build trust with their communities and save staff time.

The ParentSquare app consistently ranks among the top five free apps in the U.S., and we’ve been named to the Inc. 5000 list of America’s fastest-growing private companies four years in a row and to the Inc. Best Workplaces list for the past two years. We’re a diverse, remote-first team that cares about each other, and about the schools and families they serve. Sound like your kind of place? We’d love to have you help us build what’s next.

Schools count on ParentSquare to reach families securely and reliably every day, and the technical choices we make next will decide how well we keep that promise as we grow and as AI changes how software gets built.

ParentSquare is seeking a Principal Engineer to set our technical direction and multiply the impact of our engineering organization. You'll partner directly with our VP of Engineering, executive team, and product leaders to turn company goals into lean technical plans, own the long-term architecture of our platform, and lead how we redesign engineering workflows around LLMs and AI agents to deliver faster. This is a senior individual contributor role: your influence comes from sound business judgment, a sense of urgency, a preference for simple solutions, and the engineers you help grow.

Above all, you'll bring our two permissions to play:

• Humility. We're heads-down builders who'd rather let the work speak. In this role, that means sharing credit, choosing the simple solution over the clever one, and pulling teams toward one shared goal.
• Passion for our mission. The architecture you shape determines how securely and reliably schools reach families, and every gain in how fast we deliver means teachers and students feel the difference sooner.

• Partnering with the VP of Engineering, executive team, and product leaders to turn company goals into lean, pragmatic technical plans
• Defining our AI development roadmap, along with the practices and tools that help engineers build faster with LLMs and agents
• Owning the long-term architecture of our platform, balancing fast iteration with the security, privacy, and uptime schools require
• Raising the engineering bar through architecture reviews and design guidance across teams
• Mentoring Staff and Senior engineers and helping them grow as technical leaders
• Serving as the technical voice in conversations with key customers, partners, and executives
• Making tradeoffs with urgency and business judgment, and championing simple solutions over complex ones

• A track record of technical leadership at scale, setting direction across multiple teams and systems
• Experience designing, evolving, and maintaining complex, high-scale services in languages such as Ruby, Python, JavaScript/TypeScript, or PHP
• Deep expertise in scale, reliability, and distributed systems, including relational databases like MySQL or PostgreSQL
• A strong grounding in application and infrastructure security, with the technical depth to partner closely with security teams on threat modeling, reviews, and remediation
• Hands-on leadership in AI-assisted software engineering, with examples of workflows you've redesigned around LLMs or agents
• Strong executive presence and the ability to explain technical tradeoffs clearly to non-technical audiences

Bonus points for:

• AWS experience, especially Aurora, RDS, or SQS
• Experience working across a multi-language codebase spanning Ruby, Python, JavaScript/TypeScript, and PHP

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 shape the technical and AI direction of our platform, 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. We are committed to maintaining a drug-free workplace in compliance with applicable state laws.

The salary range for this role will be $210,000-$265,000 DOE.