Director, Insurance Operations (Remote - in certain states)

Description
YOUR ROLE
We're seeking a highly skilled and experienced Director of Insurance Operations to join our team. The Director of Insurance Operations will lead a high-performing team of Producers, Placement Specialists, and Account Managers responsible for placing and servicing commercial risks with business owners or on behalf of retail agents. This leader will be responsible for scaling the team, improving operational performance against defined SLAs, and ensuring an outstanding experience. You will partner cross-functionally with product, sales, and carrier teams to optimize placement efficiency and grow our wholesale impact in the commercial insurance market.
WHAT YOU'LL DO

• Lead and scale the operations of Bold Penguin's Digital Wholesale and Retail division, managing Producers, Placement Specialists, and Account Management teams to meet service-level agreements (SLAs) and deliver a high-quality agent experience
• Drive operational efficiency and revenue growth by building processes, workflows, and reporting structures that support the placement and servicing of commercial insurance policies across multiple carriers
• Oversee day-to-day team performance, ensuring strong execution against placement volume targets, turnaround times, and agent satisfaction metrics
• Collaborate with product, engineering, sales, and carrier relations teams to optimize the wholesale and retail platform experience and drive adoption
• Develop and implement onboarding, training, and quality control programs to elevate team performance and consistency
• Analyze performance trends and provide actionable insights to senior leadership to shape operational strategy and resourcing decisions
• Stay current on industry trends, carrier appetite changes, and market dynamics to ensure competitive positioning and proactive support to agents
• Coach, mentor, and develop team members through regular feedback, goal setting, and career development planning
• Implement continuous improvement initiatives to streamline processes and scale the team effectively as volume grows
• Other duties and responsibilities as assigned

Requirements
YOUR LOCATION
This is a fully remote role, with the exception of onboarding and optional in-office events. Candidates must reside in one of the states listed in the application questionnaire and/or below.
States in which we hire: Florida, Georgia , Illinois, Massachusetts, Ohio, Tennessee, Texas
Skills & Experience

• 7+ years of experience in commercial insurance, with at least 3 years in a team leadership or operational management role
• Prior experience in a wholesale, MGA, or brokerage environment is strongly preferred
• Proven success in scaling teams, managing to metrics/SLAs, and driving operational efficiency
• Excellent people leadership and change management skills
• Strong understanding of commercial insurance products and workflows
• Comfortable working in a fast-paced, tech-enabled environment
• Data-driven mindset with the ability to analyze and act on operational metrics
• Licensed P&C agent preferred, or willingness to obtain within 60 days

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.

Summary
Bold Penguin is a leading integrated digital solution platform dedicated to simplifying small commercial insurance. Our technology makes the quote and bind process quick, effortless, and profitable for all parties - agents, brokers, and carriers. Bold Penguin's innovative product suite has digitized and transformed a slow, manual process resulting in reduced costs, increased efficiency, and better overall outcomes. For more information, please visit www.boldpenguin.com .
Or, simply put.... We simplify commercial insurance.
Benefits
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
• Parental Leave
• 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 .