Helper Connectwise Jobs in Florida (NOW HIRING)

Service Supervisor

Location: Palm Beach Gardens, FL HQ

Schedule: 8 AM - 5 PM, Monday - Friday

Salary: $75,000 - $95,000 / year, based on experience and business unit

Reports To: Service Delivery Manager (SDM)

Travel: Up to 10%; may include need-based client site visits and occasional multi-day travel

Promotion Path: Service Delivery Manager, Account Manager

Position Summary

The Service Supervisor is the operational leader for an assigned service pod. This role owns day-to-day service execution, technician performance, SLA adherence, and board health.

This position is accountable for ensuring technicians operate with structure, discipline, and consistency so that the Service Delivery Manager can focus on strategic client leadership, profitability, and executive engagement.

The Service Supervisor does not own client strategy, QBRs, or contract accountability. Instead, this role ensures operational excellence and protects the SDM from daily execution noise. This is a leadership role focused on people management, service discipline, and operational execution.

Key Performance IndicatorsOperational Health

• 95% weekly ticket completion rate
• 85% same-day resolution rate
• 98% team-level CSAT average
• SLA compliance within assigned pod standards
• Time entry compliance 98%
• QA review of at least 5% of tickets/calls weekly
• Escalation routing compliance
• Documentation standard enforcement

What You'll OwnTeam Oversight & Enablement

• Oversee daily ticket queues, ensuring priority, urgency, and workload balance are maintained.
• Conduct daily board reviews to ensure SLA health and proactive ticket progression.
• Lead weekly team huddles to reinforce accountability and alignment.
• Conduct bi-weekly 1:1s with assigned technicians.
• Identify performance concerns and training gaps, then coordinate action plans with the SDM.
• Reinforce adherence to SOPs and documentation requirements.
• Provide structured coaching and performance feedback.

Operational Leadership

• Monitor SLA and time entry compliance across assigned pods.
• Ensure proactive work and documentation targets are met.
• Partner with the SDM on service scheduling, coverage, and resource planning.
• Support escalations by collecting operational context and coordinating responses.

Escalation & Service Coordination

• Coordinate responses to service escalations within the pod.
• Gather operational data and technician context before elevating issues to the SDM.
• Facilitate cross-team collaboration for resolution.
• Ensure escalation communication remains professional and structured.

Quality & Process Discipline

• Conduct weekly QA audits to validate service quality and documentation standards.
• Identify trends in recurring issues and recommend process improvements.
• Ensure compliance with internal operational standards and playbooks.
• Maintain board hygiene and ticket categorization accuracy.

Client Interaction

• Participate in client calls when operational context is required.
• Conduct structured operational pulse checks at the direction of the SDM.

Cadence Expectations

• Daily interaction with assigned team members.
• Daily board review to support SLA health, workload balance, and ticket progression.
• Weekly structured team huddle.
• Bi-weekly 1:1s with assigned technicians.
• Bi-weekly 1:1 with the Service Delivery Manager.
• Monthly documented coaching touchpoints.

Required Education & Experience

• High School Diploma or GED.
• 3+ years in a technical service desk or helpdesk role.
• 1+ year in a leadership, mentorship, or supervisory role.
• MSP experience strongly preferred.
• Experience with Salesforce, ConnectWise, IT Glue, or similar PSA/RMM tools.

Preferred Experience

• Prior accountability for client satisfaction, SLA performance, or team metrics.
• Experience supporting healthcare or compliance-driven clients.
• Previous exposure to client-facing service meetings or reporting.
• ITIL familiarity or service management framework exposure.

Skills Required for Success

• Strong written and verbal communication skills.
• Proven ability to coach, mentor, and hold others accountable.
• Conflict resolution and team-building capabilities.
• Analytical thinking, with the ability to interpret service metrics into action plans.
• Calm, professional presence under pressure with both clients and team members.
• Strong organizational skills and high attention to detail.
• Process-oriented and disciplined in daily execution.
• Comfortable presenting service insights to leadership and Account Managers.
• Decisive operational judgment.

Certifications

Required: None

Preferred:

• CompTIA A+ or equivalent foundational technical certification
• ITIL Foundation
• Salesforce training or certifications
• ConnectWise University or IT Glue Admin training

Certifications are a plus, but not required. Leadership, communication, operational discipline, and service execution are prioritized.

Advancement Requirements

Promotion consideration includes:

• Demonstrated accountability for team performance and client satisfaction.
• Consistent contribution to service quality improvements.
• Endorsement by the SDM and Director of Service.
• Completion of any internal leadership training programs.