[Hiring] Principal Software Engineer @ParentSquare

Role Description

We are looking for a Principal Software Engineer who serves as the ultimate technical authority and multiplier across our engineering organization. As our top-tier individual contributor, you operate with an extreme sense of urgency, high business acumen, and an unyielding commitment to simplicity.

We are seeking a deeply AI-forward, vision-driven engineer. To us, this means you don't just use AI tools—you fundamentally redesign engineering paradigms around them. You are the pioneer who sets the standard for how our entire company leverages LLMs and AI agents to accelerate cycle times, eliminate friction, and ship simple, high-impact capabilities at an unprecedented cadence. Most importantly, you are deeply passionate about transforming the lives of students and educators through seamless communication.

This role will include:

• Strategic & Executive Leadership: Partner directly with the VP of Engineering, C-Suite, Product leadership, and business stakeholders to turn ambitious company goals into lean, executable technical strategies.
• AI Strategy & Culture: Define and drive the company-wide AI development roadmap. Establish the practices, tools, and mindset needed to transform our engineering organization into a hyper-efficient, AI-native development force.
• Architecture & System Vision: Own the overarching architectural vision of our platform. Guide the long-term evolution of our services—balancing rapid iteration with the rigorous security, privacy, and uptime requirements schools demand.
• Technical Excellence & Mentorship: Elevate the engineering bar across all teams through architectural reviews, mentorship of Staff and Senior engineers, and modeling a culture of speed, rigor, and simplicity.
• Cross-Functional Influence: Serve as the technical voice of the company in high-stakes conversations with key clients, partners, and cross-functional executives to align technology with core business value.

Qualifications

• Proven track record of designing, evolving, and maintaining complex, high-scale services using Ruby, Python, JavaScript/TypeScript, and PHP.
• Deep expertise in scale, reliability, and relational databases (MySQL, PostgreSQL), alongside cloud infrastructure (AWS Aurora, RDS, SQS).
• You are a thought leader in AI-assisted software engineering, actively shaping how teams pair with AI to eliminate toil and focus on high-leverage architectural problems.
• Exceptional ability to distill complex technical trade-offs into clear business decisions for non-technical stakeholders, executives, and customers.
• Bachelor’s degree (or higher) in Computer Science or a related field, with a demonstrated history of technical leadership at scale.

Benefits

• 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
• PTO that increases each year
• 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.

Company Description

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.