Two Chicks With A Side Hustle

Lead a team supporting schools and families nationwide while guiding agents, resolving complex issues, and keeping customer experience at the center. If you’re the type who jumps in when a queue spikes, coaches others to level up, and thrives on improving support systems, this role fits like a glove.


About ParentSquare

ParentSquare is a fast-growing edtech platform transforming how schools and families communicate. Serving 22+ million students, the company provides secure messaging, forms, translations, payments, district websites, and more — all designed to build stronger school communities. The mission: empower educators and engage families for better student outcomes.


Schedule

  • Full-time, remote (U.S. only)
  • Salary range: $27–$30/hour DOE
  • Collaboration with Support Manager, Customer Support agents, and product teams

What You’ll Do

  • Coach and support a cohort of customer support agents to ensure fast, high-quality responses
  • Provide backup coverage during peak demand periods
  • Handle escalations, tier-2 tickets, and red-flag customer issues
  • Offer structured feedback to leadership on training needs and support processes
  • Lead live coaching sessions and monitor support queues for coverage
  • Assist new team members through onboarding and product training
  • Recommend improvements to workflows and long-term support strategy

What You Need

  • High school diploma + 2+ years customer support experience in SaaS/software
  • Prior leadership or team-lead experience
  • Familiarity with edtech and SIS/integration tools is a plus
  • Strong communication, detail-orientation, and organizational skills
  • Ability to manage multiple priorities in a fast-moving environment
  • Positive, service-driven mindset aligned with ParentSquare values

Benefits

  • Employer-paid health insurance (including dependents)
  • 401(k) match from day one
  • Stock options
  • Paid parental leave
  • PTO increases annually + 16 paid holidays (including your birthday!)
  • Wellness reimbursements
  • Remote work setup provided

This is a chance to step into leadership inside a growing edtech company — roles like this fill quickly, especially for those who love building others up while solving customer challenges.

Support school communities and lead a team that helps families stay connected.


Happy Hunting,
~Two Chicks…

APPLY HERE