Director of Retail Operations

This is a fully remote position, open to applicants in United States.

📋 Description

• Supervise, mentor, and cultivate the Retail account manager teams, promoting a high-performance culture that emphasizes accountability, collaboration, and ongoing improvement.

• Offer continuous coaching and feedback to enhance team performance, celebrate successes, and tackle areas needing development – guiding the creation and implementation of best practices in sales methodologies, processes, and customer engagement.

• Formulate and execute strategic plans for the Retail LOB, in alignment with organizational revenue targets and operational goals – incorporating actionable insights, business cases for new opportunities, and strategic contributions to product planning and go-to-market approaches.

• Establish clear performance expectations, evaluate team performance, and introduce training or coaching initiatives to boost skills and productivity – measuring success against KPIs evaluated quarterly and yearly.

• Direct the Retail LOB through process enhancements, technology integrations, and organizational transitions, ensuring team buy-in and alignment while utilizing data analytics to pinpoint trends and guide decision-making.

• Partner with Marketing for demand generation and customer campaigns, collaborate with CRM Systems Administration for tool optimization, engage with Program and Product Managers for market alignment, and work with Underwriters for risk assessment and product development.

• Recognize inefficiencies within sales and account management workflows and implement solutions to streamline operations and improve the customer experience.

• Champion your team by collaborating with data, systems, programs, underwriting, and learning development teams to advocate for ongoing education, streamlined workflows, and precise data tracking that enhances team success.

• Utilize CRM data and analytics to detect trends, forecast performance, and make informed strategic decisions – maintaining or improving NPS and other customer satisfaction metrics for Retail LOB clients.

• Serve as the main point of contact for internal teams, ensuring smooth communication and alignment on Retail LOB goals and cross-functional initiatives.

• Expected to perform additional duties as requested, directed, or assigned.

⛳️ Requirements

• 7+ years of experience in sales operations, retail operations, or general management — ideally within the insurance, insurtech, or a related financial services sector.

• Proven capability to lead, develop, and hold accountable high-performing sales and account management teams in a dynamic environment.

• Strong skills in strategic planning and execution with a demonstrated history of establishing and scaling operational processes.

• Experience in data-driven decision-making — adept at analyzing CRM data, performance metrics, and analytics platforms (HubSpot preferred; Power BI or similar).

• Exceptional cross-functional collaboration and stakeholder management abilities with a talent for building strong relationships across Sales, Marketing, Product, and Underwriting.

• Strong coaching and team development instincts, with a proven record of nurturing talent and driving performance enhancement.

• Demonstrated skill in identifying operational inefficiencies and executing scalable solutions.

• Excellent verbal and written communication skills, with the capability to convey goals, strategies, and expectations to varied audiences.

• Proficiency in Microsoft Office Suite, Google Drive, HubSpot, and analytics platforms.

• Familiarity with insurance sales practices, market segments, and regulatory compliance is preferred.

🏝️ Benefits

• Health, dental, and vision plans.

• Excellent work-life balance with 4 weeks of Paid Time Off.

• 10 Paid Company Holidays plus 2 floating holidays.

• 401K Programs with employer matching.

• Personal assistance programs to support a healthy personal and work life.