Operational Support Specialist Manager

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

• Other Compensation Annual Performance Bonus Eligible
• Job Category Customer Success, People Management, Commercial Insurance
• Relocation Expense Covered No
• Employee Type FT Exempt
• Travel 5%

Description

YOUR ROLE

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.

WHAT YOU'LL DO

Team Support Performance & Issue Resolution

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

Operational Execution & Workflow Health

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

Workflow Quality & Continuous Improvement

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

Collaboration & Service Excellence

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

Requirements

YOUR LOCATION

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

Skills & Experience

• 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

Physical Requirements

• 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.

Summary

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.

We offer competitive compensation and progressive benefits that include:

• Medical, Dental, and Vision
• Flexible PTO Policy
• 401(k) with a company match
• Employee Assistance Program
• Disability and Life Benefits

Stay connected to the Glacier.

We have great SLACK channels for work and play. We also like to video conference and hold all-hands "Waddles" regularly.

Penguin bling.

Like swag themed after a certain Antarctic bird? Just. You. Wait.

Bold Penguin believes in inclusion. That's why we’re proud to be an equal opportunity employer that considers all qualified applicants regardless of race, color, religion, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. To learn more about our results-focused culture and employee-focused perks, read more on our careers page.