Remote Operations & Support Manager

OhioX; Dublin (OH); Remote; USD 75,000 - 85,000; Full time

Benefits offered by this job

Medical, Dental, and Vision

Flexible PTO Policy

401(k) with a company match

Employee Assistance Program

Parental Leave

Disability and Life Benefits

Job summary

Bold Penguin is the premier digital broker for commercial insurance. The Operational Support Specialist (OSS) Manager leads the OSS team, ensuring fast, accurate agent support while backend workflows run smoothly.

This remote role partners with Customer Success, Compliance, Carrier Ops, Product, and Engineering to maintain operational excellence and scale a seamless agent experience. The OSS Manager focuses on coaching, process optimization, SLA ownership, and high-quality support across live

Qualifications

• 7+ years in a customer support role.
• 3+ years leading support teams in fast-paced environments.
• Experience managing operations using Intercom preferred.
• Strong people leadership, coaching, and performance management.
• Excellent multitasking, prioritization, and problem-solving.
• Proficiency with Google Suite, ticketing systems, CRMs, and chat platforms.
• Detail-oriented with quality control mindset.
• Comfortable with backend workflows and technical issues.
• Commercial insurance operations or SaaS support experience preferred.
• Self-motivated, action and results-oriented.
• Exceptional written and verbal communication.
• Bachelor's degree or equivalent practical experience.

Responsibilities

• Lead real-time agent support across live chat, email, and case management.
• Monitor queues, response times, and backlog to ensure SLA performance.
• Coach OSS team on troubleshooting platform issues and escalations.
• Serve as escalation point for complex blockers and document standards.
• Oversee carrier appointment processing and market access workflows.
• Ensure data corrections and backend fixes are completed promptly.
• Identify workflow bottlenecks and redistribute workload to maintain throughput.
• Audit OSS work for accuracy and SOP adherence.
• Collaborate with Carrier Ops, Product, and CS to improve workflows.
• Own escalation handoffs and timely resolution across teams.

Skills

Agent Leadership

SLA Monitor

Troubleshooting

Escalation

Documentation

Communication

People Leadership

Education

Bachelor's degree

Tools

Intercom

Google Suite

Salesforce

Ticketing systems

Job description

Bold Penguin is the premier digital broker for commercial insurance. The Operational Support Specialist (OSS) Manager leads the OSS team, ensuring fast, accurate agent support while backend workflows run smoothly.

This remote role partners with Customer Success, Compliance, Carrier Ops, Product, and Engineering to maintain operational excellence and scale a seamless agent experience. The OSS Manager focuses on coaching, process optimization, SLA ownership, and high-quality support across live