Customer Support Agent, Tier 2

ParentSquare

4d•$27 - $29•Remote

About The Position

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.

Requirements

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.

Responsibilities

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 escalate 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.