Operational Support Specialist Manager

• Location:
  
  Remote - United States
• Base Pay: $75,000.00 - $85,000.00 / Year
• Other Compensation:
  Annual Performance Bonus Eligible
• Job Category:
  Customer Success, People Management, Commercial Insurance
• Relocation Expense Covered:
  No
• Employee Type: FT Exempt
• Travel: 5%

The Operational Support Specialist (OSS) Manager is the frontline people leader and operational owner behind Bold Penguin's agent support experience. The OSS Manager leads and coaches the Operational Support Manager team, ensuring agents receive fast, accurate, and friction-free support while backend operational workflows are executed consistently and to a high standard. This role sits at the intersection of customer support leadership, process optimization, SLA performance ownership, workflow health, quality control, and continuous improvement across the OSS function.

The OSS Manager partners closely with Customer Success, Compliance, Carrier Ops, Product, and Engineering to maintain operational excellence, remove friction, and scale a seamless agent experience.

• Lead real-time agent support across live chat, email, and case management
• Monitor queues, response times, and backlog health to ensure SLA performance
• Coach OSS team members on troubleshooting platform issues, including those related to submissions, logins, integrations, and API errors
• Serve as an escalation point for complex technical and operational blockers
• Ensure clear documentation and communication standards across all cases

• Oversee carrier appointment processing and market access workflows, ensuring accuracy and efficiency
• Ensure data corrections and backend fixes are completed promptly and correctly
• Proactively identify workflow bottlenecks and redistribute workload as needed, maintaining predictable throughput and low backlog across OSS operations

• Audit OSS work for accuracy, completeness, and SOP adherence
• Reduce rework, errors, and avoidable escalations through coaching and process refinement
• Identify recurring friction points impacting agents or internal teams
• Contribute to SOP updates, training materials, and knowledge base improvements

• Partner with Carrier Ops, Product, and CS to improve workflows, tooling, and user experience
• Own escalation handoffs and resolution timelines across teams
• Ensure service-level goals for responsiveness, accuracy, and resolution are consistently met
• Foster a calm, solutions-focused, and customer-first support culture
• Represent OSS in operational reviews and cross-team planning sessions

This is a fully remote role, with the exception of onboarding and optional in-office events.

• 7+ years of experience in a customer support role
• 3+ years of experience leading support teams in fast-paced environments
• Experience in establishing and direct management of support operations using FIN (Intercom) is strongly preferred
• Strong people leadership, coaching, and performance management skills
• Excellent multitasking, prioritization, and operational problem-solving ability
• Proficiency with Google Suite, ticketing systems, CRMs (Salesforce preferred), and chat platforms
• Highly detail-oriented with a strong quality control mindset
• Comfortable navigating technical issues and backend workflows
• Commercial insurance operations and/or SaaS support experience strongly preferred
• Self-motivated, action and results-oriented
• Exceptional written and verbal communication
• Bachelor's degree or equivalent practical experience

• Must be able to sit/stand/walk for prolonged periods of time, (up to 8 hours per day) at a desk working on a computer.
• Must be able to use standard office equipment for extended periods of time, including but not limited to, a mouse, keyboard, phone and video conferencing.
• Must be able to travel to the Bold Penguin office in Dublin, Ohio for New Hire Onboarding & Orientation (2 days, 2 nights); travel costs are covered by Bold Penguin.
• Must be able to travel occasionally for corporate events and team planning sessions.

Bold Penguin is the premier digital broker for commercial insurance. Their technology expands top-of-funnel demand and increases yield for enterprise partners. Through digital distribution, wholesale capabilities, and AI-driven insights, they transform the lifecycle of both simple and complex risks, from prospecting to placement.

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