Director of Operations and Security

Who We Are

ParentSquare is a rapidly growing Santa Barbara-based company that’s changing the way schools and parents communicate every day. Sound simple? We strive to keep it that way! Our mission is to give schools the power to incredibly enhance family engagement for all students. ParentSquare and RemindHub, our flagship products, serve over 20 million students and drive our mission by providing unified communications tools -forms, sign ups, payments, RSVPs, direct messaging, language translations, chat and more. Remind Chat, our free product, reaches over 80% of K-12 students, providing a safe and easy-to-use platform for direct communication between teachers and families. And our latest innovation, SmartSites, offers state-of-the-art websites for school districts, enhancing their online presence and accessibility. 

We are not just creating a product; we are creating empowered educators and engaged parents to improve the lives of all students.  We are passionate advocates for our  customers and for our employees and we invite you to join us on this exciting journey. 

Who We’re Looking for

At ParentSquare, we’re passionate about improving the lives of students, and that passion drives how we build our product and serve our customers. We’re seeking a results-driven Director of Operations and Security to join our Engineering management and leadership team. In this role, you will lead software development and infrastructure initiatives, ensuring product scalability, performance, and security while delivering simple, powerful features that schools and districts trust. You’ll collaborate cross-functionally with product, design, sales, and marketing teams to align technical strategies with business goals and customer needs. You’re someone with a proven track record of developing and implementing forward-looking technology strategies, advocating for DevOps and security best practices and fostering automation to eliminate repetitive tasks. You will oversee site reliability operations, ensuring system stability, monitoring, capacity planning, incident response, and disaster recovery while administering tools for SRE metrics and improvements. Working directly with our Chief Technology Officer, you will mentor a team of engineers, foster a culture of collaboration and continuous improvement, and maintain hands-on involvement in technical decision-making.  

This role will include:

• Working closely with the CTO to set clear expectations – and beat those expectations- as you deliver on our platform.

• Building and leading your team as you execute each sprint to the best of your ability.

• Collaborating with your peer engineering managers and leaders to meet (and beat!) our company goals

• Participating in the hiring process as we continue to build our team.

• Holding technical staff accountable to balance delivery with quality.

• Leading our incident management process to ensure our customers get the best experience at all times.

• Ensuring our policies are properly followed and tracked with ITSC, and building integrations between systems (e.g., Vanta) to streamline tracking and enforcement.

• Working with the CTO and finance to track infrastructure spend and identify unexpected expenses.

• Carrying out and implementing security initiatives with the CTO/ITSC.

• Automating maintenance of systems alongside SREs.

• Helping product and engineering teams build a culture of cost and security awareness.

• On any given day, you might be reviewing PRs, helping a team accelerate delivery, finding a subtle production issue, evaluating vendors or designing the future architecture of our systems.

What to expect:

• Daily: 

• Track alerts from Vanta/Datadog to identify high-priority work.

•  Push team to meet sprint goals.

• Weekly:

• With ITSC, triage and assign maintenance work across Remind, ParentSquare, and SmartSites systems.

• Collaborate with product/engineering teams to carry out maintenance.

• Integrate/build/extend tests and sources into Vanta.

• Quarterly:

• Work with the CTO to track infrastructure spend across multiple vendors.

• With ITSC and CTO, identify expansion opportunities for security and compliance.

• Identify automation opportunities to reduce maintenance load on engineering teams.

• Annually:

• Coordinate pentests, security training, and compliance audits with ITSC and CTO.

Our ideal candidate will have the following:

• 5 years of proven Engineering leadership experience

• 8 years of experience of Site Reliability Engineering and DevOps

• Exposure to large-scale services on Ruby/Python and JavaScript/TypeScript

• Familiar with service and application development with MySQL/Postgres

• Familiar with deploying and operating systems at scale on AWS/Aurora/RDS/SQS

• Experience working with vendors and hitting budget targets

• Bachelor’s degree (or higher) from an accredited college or university in Computer Science or related field.

• Familiar with incremental, agile development processes, as well as CI/CD

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

• 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. 

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 to $225,000, DOE. 

Salary : $175,000 - $225,000