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.

Every team at ParentSquare is asking what AI can do for their work, and our new AI Platform team exists to find the answers worth building.

ParentSquare is seeking an Engineer to build the tools that help everyone at ParentSquare put AI to work. As one of the team's first engineers, you'll help shape how it operates from day one and have a real hand in how a whole company integrates AI into their daily workflow. This is not a traditional software role: there's no fixed stack, so you'll pick the right tool for each problem, and requests often arrive as a simple "can AI fix this?" You'll spend about as much time with Support, Customer Success, and Product as you do writing code, most of what you build will be internal, and some of it will be retired once it has done its job.

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

• Humility. We're heads-down builders who'd rather let the work speak. Here, that means listening closely to the teams you serve, sharing what you learn with fellow engineers, and retiring your own tools when they stop helping.
• Passion for our mission. The time your tools give back to our Support, Customer Success, and Product teams goes into serving schools, and the care you put into evaluating model output protects the students and families who count on us.

• Building and shipping tools that put LLMs and agents to work across ParentSquare
• Turning open-ended requests into scoped problems, and saying no to the ones that aren't worth building
• Owning adoption: measuring whether your tools get used, then improving or retiring the ones that don't
• Evaluating model output for accuracy, cost, and failure modes before anything reaches schools
• Building features that run reliably at scale and meet the security and privacy standards K-12 requires
• Working within our existing systems, including our monolith, and taking an active part in code reviews
• Sharing AI development practices across engineering and helping peers find what works
• Contributing to a culture of clear, simple code and continuous learning

• Professional experience shipping production backend services in Ruby, Python, JavaScript/TypeScript, or PHP; the craft matters more than the language
• A clear record of changing how you work with LLMs and agents, with concrete examples of what worked and what didn't
• Solid experience building application services on MySQL or PostgreSQL, beyond standard ORM use
• Proficiency building and consuming RESTful APIs
• Experience deploying, monitoring, and operating services on cloud infrastructure
• Comfort turning ambiguous requests from non-technical partners into working solutions

Bonus points For:

• AWS experience, especially Aurora, RDS, or SQS
• Experience with distributed systems or evolving monolithic architectures
• A history of building internal tools that other teams came to rely on
• Experience in K-12, EdTech, or another domain with significant privacy and security constraints

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 be one of the first engineers on our new AI Platform team, 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 $135,000- $185,000 DOE.