Remote Operational Support Manager- Customer Success Leader

Bold Penguin, Inc.; Dublin (OH); Remote; USD 110,000 - 160,000; Full time

Benefits offered by this job

Medical, Dental, and Vision

Flexible PTO Policy

401(k) with company match

Employee Assistance Program

Disability and Life Benefits

Job summary

Bold Penguin, Inc. is hiring an Operational Support Specialist (OSS) Manager to lead the OSS team and own the end-to-end agent support experience. You will drive real-time agent performance, partner with CS, Compliance, Carrier Ops, Product, and Engineering, and ensure scalable, high-quality support across channels.

The role is fully remote with onboarding in Dublin, Ohio and occasional in-office events. You will coach a team, optimize workflows, and champion a customer-first culture while

Qualifications

• 7+ years in a customer support role.
• 3+ years leading support teams in fast-paced environments.
• Experience with FIN (Intercom) is strongly preferred.
• Strong people leadership and performance management.
• Excellent multitasking and problem solving.
• Proficiency with CRM, ticketing systems, and chat platforms.
• Bachelor’s degree or equivalent practical experience.

Responsibilities

• Lead real-time agent support across live chat, email, and case management.
• Coach OSS team on troubleshooting platform issues and back-end workflows.
• Ensure SLA performance and backlog health through monitoring.
• Oversee carrier appointments and market access workflows for accuracy.
• Identify workflow bottlenecks and drive continuous improvement.
• Collaborate with CS, Product, and Engineering to optimize tooling and processes.
• Own escalation handoffs and timely resolutions across teams.

Skills

People leadership

Customer support

SLA management

Problem solving

Intercom familiarity

CRM tools

Communication

Cross-functional collaboration

Education

Bachelor's degree or equivalent

Tools

Intercom

Salesforce

G Suite

Ticketing systems

Job description

Bold Penguin, Inc. is hiring an Operational Support Specialist (OSS) Manager to lead the OSS team and own the end-to-end agent support experience. You will drive real-time agent performance, partner with CS, Compliance, Carrier Ops, Product, and Engineering, and ensure scalable, high-quality support across channels.

The role is fully remote with onboarding in Dublin, Ohio and occasional in-office events. You will coach a team, optimize workflows, and champion a customer-first culture while