Site Reliability Engineer, Team Lead – Monitoring & Support

• Location
• Remote | Hybrid to Wayne, PA | Hybrid to Naperville, IL
• How you’ll contribute to our mission

At Frontline Education, our mission is clear: we transform how schools work, so every educator and student succeeds.

Our vision is every school thriving.

Every community stronger.

Reliable technology is essential to making that possible.

As the Site Reliability Engineer Team Lead for Monitoring & Support, you’ll lead our 24/7 monitoring and first-response function, including globally distributed team members, helping ensure the systems our customers rely on are monitored thoughtfully and supported consistently.

You’ll create an environment where alerts lead to meaningful action, documentation makes teams more effective, and escalations happen with the right context and urgency.

You’ll help the team understand the impact behind an incident, not simply respond to the alert, so decisions reflect what matters most to the educators and school communities we serve.

This is primarily a leadership role with meaningful hands‑on technical involvement.

You’ll analyze telemetry, improve dashboards and alerting strategies, strengthen incident response practices, and explore practical uses of AI and large language models to help the team identify patterns, accelerate triage, improve documentation, and make better-informed decisions.

You’ll model ownership when challenges arise, bring teams together to solve problems, and continually look for ways to improve the reliability and support experience we provide to our customers.

• How you’ll drive success
• Lead the day-to-day work of Level 1 support engineers, creating clear expectations for ownership, communication, collaboration, and operational excellence while managing offshore staffing, schedules, and rotations to maintain effective 24/7 coverage.
• Oversee and continuously improve monitoring practices, including alert thresholds, health checks, dashboards, and routing.

Reduce unnecessary noise while ensuring meaningful signals reach the right people at the right time.

• Lead initial production incident triage by validating alerts, understanding customer and business impact, assessing urgency, gathering relevant context, and partnering with development and platform engineering teams to accelerate diagnosis and escalation.
• Build strong partnerships across engineering and support teams.

Share context openly, clarify ownership, and help teams work together toward durable solutions rather than short‑term fixes.

• Maintain high‑quality runbooks, knowledge‑base content, shift handoffs, and incident documentation that enable consistent response and faster recovery.

Turn lessons from incidents into practical improvements to monitoring, processes, and team readiness.

• Apply AI and LLM‑enabled tools thoughtfully to accelerate log and telemetry analysis, summarize incident context, surface relevant knowledge, and identify patterns that may otherwise take significant manual effort to uncover.
• Identify repetitive triage and support activities that can be responsibly automated.

Test new approaches, validate outputs, protect sensitive information, and maintain appropriate human judgment for decisions that affect production systems and customers.

• Define and continuously improve processes for alert routing, escalation, status updates, stakeholder communication, change control, and operational readiness.
• Use operational trends and incident data to identify recurring issues and improvement opportunities, helping the team move from reacting to individual alerts toward preventing future disruption.
• Take ownership of outcomes, especially when responsibilities cross team boundaries.

Keep the customer impact visible in decision‑making and communicate clearly until issues reach an appropriate resolution.

What you bring to help us grow

• 5+ years of experience in monitoring, incident triage, site reliability, production support, or a related operational environment, including at least 1 year of team leadership experience.
• Strong knowledge of monitoring and application performance management tools such as Dynatrace, Nagios, Prometheus, Datadog, or similar platforms, including experience improving alerts and dashboards.
• Experience using log analysis platforms such as ELK or Splunk to investigate production behavior and support incident diagnosis.
• Working knowledge of scripting languages such as Python or Bash and the ability to use automation to improve repetitive operational workflows.
• Familiarity with incident management platforms such as Pager Duty or Opsgenie, ticketing systems such as Jira, and collaboration tools such as Slack or Microsoft Teams.
• Strong written and verbal communication skills, with the ability to create clear technical documentation and provide effective leadership to globally distributed teams.
• Experience using, evaluating, or experimenting with LLMs, generative AI, or agentic AI approaches to improve triage, analysis, documentation, or operational workflows.
• Experience working with IT Service Management processes and practices. Familiarity with ITIL principles is beneficial.
• Experience operating within large‑scale enterprise environments and supporting services where reliability, communication, and disciplined operational practices are critical.
• What you’ll need to thrive

You’ll be most successful in this role if you combine technical depth with curiosity, sound judgment, and a strong sense of ownership.

You’re comfortable moving between leadership and hands‑on investigation, and you stay focused on the outcome when an incident crosses systems, teams, or time zones.

You ask questions to understand what is happening and who is affected before jumping to a solution.

You collaborate openly with support, engineering, and platform partners, sharing what you know and inviting different perspectives because reliable services are built through strong teams, not individual heroics.

You continually look for ways to make monitoring, processes, documentation, and tooling better.

You’re willing to experiment with emerging technologies, including AI, while validating their output and applying appropriate human judgment.

Most importantly, you understand that behind every alert is a service someone depends on.

You bring that customer perspective into prioritization, escalation, communication, and continuous improvement.

Our Mission, Our People, Our Purpose

At Frontline Education, we’re reimagining what’s possible by becoming an AI‑first organization, transforming how we think, work, and serve the educators who shape our schools every day.

By using AI in thoughtful, practical ways, we’re creating tools that help educators save time, gain insights, and focus more on what matters most — their students.

• How We Support Growth, Balance, and Well-Being
• Personalized Time Off: Take time when it’s needed most — whether that’s a family vacation, a reset day, or simply time to rest and refocus.
• Paid Sick Time: Separate, dedicated sick leave to care for yourself or loved ones.
• Volunteer Time Off: Paid time to give back and support causes that matter to you.
• Ten Paid Holidays: Enjoy meaningful moments and traditions throughout the year.
• Our Philosophy: We believe time away from work helps you bring your best self to it.
• Continuous Learning and Growth
• World‑Class Learning Access: Explore thousands of on‑demand courses through platforms like Linked In Learning.
• Leadership & Technical Skill Building: Develop new capabilities and chart your own professional path.
• AI Empowerment: Use Open AI tools to build fluency with emerging technology and harness AI as a creative partner for innovation and problem‑solving.
• Tuition Reimbursement: Invest in formal education to advance your skills and career.
• Ongoing Learning Culture: Participate in company‑led webinars on AI, inclusion, and industry trends—designed to inspire curiosity and continuous improvement.
• Health, Happiness, and Purpose
• Wellness Initiatives: Company-sponsored programs that support physical, mental, and emotional well‑being.
• Employee Assistance Program (EAP): Confidential support for you and your family’s needs.
• Comprehensive Benefits: Health and financial benefits that support your happiness and future.
• A Culture That Cares: At Frontline Education, we want every team member to learn, grow, and thrive—personally, professionally, and purposefully.

Compensation & Benefits

The salary range for this position is $125,000 - $145,000 and commensurate with your experience, skills, and internal equity.

In addition to base salary, you will be eligible for performance‑based incentives aligned to individual, team, and company results.

You’ll also have access to a comprehensive benefits package designed to support your well‑being and future, including healthcare coverage, retirement savings with company match, employee stock purchase opportunities where applicable, and the time‑off, wellness, and learning programs outlined above.

Specific details will be shared during the interview process.

Inclusion, Belonging & Equal Opportunity

Frontline Education is an equal opportunity/affirmative action employer.

We aspire to have an inclusive workplace and strongly encourage suitably qualified applicants from a wide range of backgrounds to apply and join our team.

Interview Process & Data Privacy

As part of our interview process, Frontline uses video conferencing tools that include photo capture and may include automated transcription features.

A screenshot or photo will be taken at the start of the interview for internal identification and record‑keeping purposes only, and transcription may be used to support notetaking and evaluation consistency.

These materials are used solely by our recruiting and hiring teams, stored securely, and not shared outside the hiring process.

Candidates may opt out of the transcription at any time by notifying their recruiter in advance.

Frontline processes this information in accordance with applicable data privacy laws and only for legitimate business purposes related to recruitment and hiring.

Your privacy is important to us. Please see Frontline’s general Privacy Statement and Applicant Privacy Statement for more information.

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