Remote OSS Manager — Customer Success Leader

OhioX; United States; Remote; USD 110,000 - 150,000; Full time

Benefits offered by this job

Annual Performance Bonus Eligible

Job summary

Bold Penguin is seeking an Operational Support Specialist (OSS) Manager to lead the OSS team, ensure fast and accurate agent support, and maintain high standards across workflows. This role collaborates with CS, Compliance, Carrier Ops, Product, and Engineering to drive operational excellence and scale a seamless agent experience.

The OSS Manager will oversee real-time support, workflow health, and continuous improvement while maintaining a customer-first culture and strong escalation

Qualifications

• 7+ years in customer support
• 3+ years leading support teams
• Experience with Intercom (FIN) preferred
• Strong leadership and performance management
• Excellent multitasking and problem-solving
• Proficiency with Google Suite, CRMs, and chat platforms
• Detail-oriented with quality control mindset
• Comfort with back-end workflows
• Commercial insurance/SaaS support experience preferred
• Self-motivated and results-oriented
• Excellent 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 health to meet SLA
• Coach OSS team on troubleshooting platform issues including submissions and API errors
• Escalate complex technical/operational blockers
• Oversee carrier appointment processing and market access workflows
• Audit OSS work for accuracy and SOP adherence
• Collaborate with Carrier Ops, Product, and CS to improve workflows
• Own escalation handoffs and resolution timelines
• Ensure SLAs for responsiveness, accuracy, and resolution

Skills

7+ years customer support

Leadership experience

Intercom/FIN experience

Coaching & performance mgmt

Multitasking & problem-solving

CRM & chat platforms

Quality control mindset

Backend workflows

Insurance/SaaS support

Communication skills

Bachelor’s degree or equivalent

Education

Bachelor's degree

Tools

Intercom

Salesforce

Google Workspace

Job description

Bold Penguin is seeking an Operational Support Specialist (OSS) Manager to lead the OSS team, ensure fast and accurate agent support, and maintain high standards across workflows. This role collaborates with CS, Compliance, Carrier Ops, Product, and Engineering to drive operational excellence and scale a seamless agent experience.

The OSS Manager will oversee real-time support, workflow health, and continuous improvement while maintaining a customer-first culture and strong escalation