Director of Retail Operations

Role Overview

• Oversee, mentor, and develop the Retail account manager teams, fostering a high-performance culture focused on accountability, collaboration, and continuous improvement
• Provide consistent coaching and feedback to optimize team performance, reinforce achievements, and address areas for improvement – leading the development and execution of best practices in sales methodologies, processes, and customer engagement
• Develop and execute strategic plans for the Retail LOB, aligning with organizational revenue goals and operational objectives – including actionable insights, business cases for new opportunities, and strategic input into product planning and go-to-market strategies
• Set clear performance expectations, monitor team performance, and implement training or coaching programs to enhance skills and productivity – tracking success against KPIs measured quarterly and annually
• Lead the Retail LOB through process improvements, technology integrations, and organizational changes, ensuring team adoption and alignment while leveraging data analytics to identify trends and inform decision-making
• Collaborate with Marketing for demand generation and customer campaigns, CRM Systems Administration for tool optimization, Program and Product Managers for market alignment, and Underwriters for risk assessment and product development
• Identify inefficiencies in sales and account management workflows and implement solutions to streamline operations and enhance the customer experience
• Serve as an advocate for your team by partnering with data, systems, programs, underwriting, and learning development teams to build cases for continued education, streamlined workflows, and accurate data tracking that drives team success
• Leverage CRM data and analytics to identify trends, forecast performance, and drive informed strategic decisions – maintaining or improving NPS and other customer satisfaction metrics for Retail LOB clients
• Act as the primary point of contact for internal teams, ensuring seamless communication and alignment on Retail LOB objectives and cross-functional initiatives
• Required to perform other duties as requested, directed, or assigned

Requirements

• 7+ years of experience in sales operations, retail operations, or general management — preferably within insurance, insurtech, or a related financial services environment
• Proven ability to lead, develop, and hold accountable high-performing sales and account management teams in a fast-paced environment
• Strong strategic planning and execution skills with demonstrated experience building and scaling operational processes
• Experience with data-driven decision making — proficiency analyzing CRM data, performance metrics, and analytics platforms (HubSpot preferred; Power BI or similar)
• Excellent cross-functional collaboration and stakeholder management skills with the ability to build strong relationships across Sales, Marketing, Product, and Underwriting
• Strong coaching and team development instincts with a track record of growing talent and driving performance improvement
• Demonstrated ability to identify operational inefficiencies and implement scalable solutions
• Excellent verbal and written communication skills with the ability to articulate goals, strategies, and expectations to diverse audiences
• Proficiency with Microsoft Office Suite, Google Drive, HubSpot, and analytics platforms
• Knowledge of insurance sales practices, market segments, and regulatory compliance preferred.

Benefits

• Health, dental, and vision plans
• Amazing work-life balance with 4 weeks of Paid Time Off
• 10 Paid Company Holidays with 2 floating holidays
• 401K Programs with employer match
• Personal assistance programs for support in a healthy personal and work life