Customer Support Agent, Tier 2

ParentSquare, Inc.; Northern (KY); Hybrid; USD 55,000 - 75,000; Full time

Benefits offered by this job

Employer-matched 401K from day 1

Stock options

Health + wellness reimbursements

PTO increases yearly

15 paid holidays

Job summary

ParentSquare, Inc. is seeking a Tier 2 Customer Support Agent to resolve complex issues across email, chat, and phone. You will leverage Zendesk and Jira to document and track escalations while delivering empathetic, high-quality service to teachers, parents, and administrators.

As a remote team member, you will help maintain knowledge of all features and contribute to improving support processes. This role emphasizes reliability, collaboration, and a passion for student success.

Qualifications

• 2+ years of customer or technical support experience, preferably in EdTech, K-12, or SaaS.
• Experience with ticketing systems such as Zendesk and Jira is highly valued.
• Strong written and verbal communication with empathy and attention to detail.

Responsibilities

• Answer emails, live chats, and phone calls, focusing on Tier 2 escalations and complex troubleshooting.
• Clarify customer needs, identify root causes, apply technical solutions, and follow up for complete resolution.
• Use Zendesk Agent Co-Pilot and record accurate notes in the ticket system.
• Create Jira issue templates for bugs or edge cases to share with engineering.
• Monitor support queues and handle overflow across channels as needed.
• Keep deep knowledge of all ParentSquare features to educate customers and support internal teams.
• Collect actionable customer feedback for Product, Success, and leadership.
• Contribute to internal docs, help articles, and feature testing.

Skills

Customer support

Zendesk

Jira

Communication

Time management

Tools

Zendesk

Jira

Job description

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 22 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:

A Tier 2 ParentSquare Customer Support Agent has advanced technical troubleshooting skills, customer service excellence, and deep empathy in their DNA. You are a true champion for our customers—from parents and teachers to district and school administrators. You step in to handle complex escalations, high-touch support issues, and live channels (email, chat, and phone) without ever sacrificing the customer experience.

As an escalation resource, you know our product inside and out, leverage modern support tools like Zendesk Agent Co-Pilot, and serve as a reliable intermediary when issues need further engineering or product involvement. You are proactive, thrive on solving intricate problems, and take pride in mentoring peers and driving continuous improvement across the Support team.

Most importantly, you’re someone who shares in our passion for improving the lives of students through communication.

This role will include:

• Answering incoming emails, live chats, and phone calls as scheduled, with a heavy focus on Tier 2 escalations and complex product troubleshooting.
• Resolving advanced product or service problems by clarifying customer needs, identifying root causes, executing technical solutions, and following up to ensure complete resolution.
• Utilizing Zendesk Agent Co-Pilot and taking detailed, accurate notes on all interactions within our ticketing system.
• Filing clean, complete Jira issue templates to elevate technical bugs or edge cases to higher-tier support and engineering teams when needed.
• Proactively monitoring support queues across all channels and stepping in to handle overflow whenever necessary.
• Maintaining deep, updated knowledge of all ParentSquare features to educate customers and act as a knowledge resource for internal teams.
• Collecting and recording actionable customer feedback to share with Product, Customer Success, and leadership.
• Assisting with internal support documentation, help articles, and product testing for new feature releases.

Our ideal candidate will have the following:

• 2+ years of prior customer support or technical support experience (EdTech, K-12, or SaaS experience highly preferred).
• Demonstrated experience with ticketing systems (Zendesk and Jira expertise strong pluses).
• Familiarity with technical integrations, data flows (SFTP, API), or Student Information Systems (SIS).
• Proven track record of handling high-volume tickets, live chats, and phone queues simultaneously with exceptional attention to detail.
• Strong written and verbal communication skills with a warm, empathetic tone.
• A proactive, self-motivated mindset with an eagerness to learn in a fast-paced environment.
• Flexibility to work varied schedules, including occasional early mornings, evenings, or weekends as coverage requires.

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:

• An employer-matched 401K retirement savings program from day 1
• 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. We are committed to maintaining a drug-free workplace in compliance with applicable state laws.

The salary range for this role will be [ xxx ], DOE.