Operational Support Specialist Manager

Bold Penguin•Dublin, OH

4d•Remote

About The Position

The Operational Support Specialist (OSS) Manager is the frontline people leader and operational owner of Bold Penguin’s agent support experience. The role leads and coaches the Operational Support Manager team, ensuring agents receive fast, accurate, friction-free support and backend workflows are completed consistently to a high standard. It spans customer support leadership, process optimization, SLA performance, workflow health, quality control, and continuous improvement. The OSS Manager partners with Customer Success, Compliance, Carrier Ops, Product, and Engineering to maintain operational excellence, remove friction, and scale a seamless agent experience. This is a fully remote role, except for onboarding and optional in-office events. The employee must travel to Bold Penguin’s Dublin, Ohio office for two days and two nights of new-hire onboarding and orientation; travel costs are covered by Bold Penguin. Occasional travel for corporate events and team planning sessions is also required.

Requirements

7+ years of experience in a customer support role.
3+ years of experience leading support teams in fast-paced environments.
Strong people leadership, coaching, and performance management skills.
Excellent multitasking, prioritization, and operational problem-solving ability.
Proficiency with Google Suite, ticketing systems, CRMs, and chat platforms.
High attention to detail and a strong quality-control mindset.
Comfort navigating technical issues and backend workflows.
Self-motivated, action- and results-oriented approach.
Exceptional written and verbal communication.
Bachelor’s degree or equivalent practical experience.
Ability to sit, stand, or walk for prolonged periods, up to 8 hours per day, while working at a desk on a computer.
Ability to use standard office equipment for extended periods, including a mouse, keyboard, phone, and video-conferencing equipment.
Ability to travel to the Bold Penguin office in Dublin, Ohio for new-hire onboarding and orientation (2 days, 2 nights), and occasional travel for corporate events and team planning sessions.

Nice To Haves

Experience establishing and directly managing support operations using FIN (Intercom) is strongly preferred.
Salesforce experience is preferred.
Commercial insurance operations and/or SaaS support experience is strongly preferred.

Responsibilities

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 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 cases.
Oversee carrier appointment processing and market access workflows, ensuring accuracy and efficiency.
Ensure data corrections and backend fixes are completed promptly and correctly.
Identify workflow bottlenecks and redistribute workload as needed to maintain predictable throughput and low backlogs.
Audit OSS work for accuracy, completeness, and adherence to standard operating procedures.
Reduce rework, errors, and avoidable escalations through coaching and process refinement.
Identify recurring friction points affecting 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, customer-first support culture.
Represent OSS in operational reviews and cross-team planning sessions.