CSC Licensed Service Supervisor

About the Company

Simply Business is a digital insurance brokerage specializing in protecting small businesses. We simplify the insurance-buying process by combining technology, data, and insurance knowledge. Our proprietary platform allows small business owners to compare quotes from over 20 top-rated providers, customize coverage, and purchase policies online. Founded in the UK in 2005, Simply Business is an insurtech pioneer with nearly 20 years of experience supporting small businesses. We are passionate about building an outstanding product and fostering an inclusive, innovative culture. Simply Business has been consistently recognized as a best place to work, including ranking in Built In’s 2025 Best Companies to Work for in the US (Top 100) and Best Places to Work in Boston.

About the Role

At the core of Simply Business is our Customer Solutions Center (CSC), which houses our Licensed Insurance Agents who interact with current and prospective customers. As we continue to grow, we are seeking a hands-on supervisor for our team of Licensed Service Agents. This role involves leading, coaching, and empowering a team to deliver exceptional customer experiences while adhering to performance and compliance standards.

Responsibilities

• Manage individual and team delivery against the service agent performance framework: Contact Delivery, Customer Impact, and CSC Standards.
• Monitor real-time phone behaviors, break thresholds, and after-call wrap times.
• Collaborate and manage performance root cause analysis and action plans to identify performance gaps.
• Lead, monitor, motivate, and evaluate day-to-day performance at both team and individual levels.
• Ensure company processes and procedures are adhered to by the team and individuals.
• Partner with quality, operations, product, and service support teams to meet compliance requirements.
• Collaborate cross-functionally to align operational initiatives with the broader customer experience strategy.
• Oversee Zendesk queue management, prioritizing complex requests for internal and external customers.
• Guide the team through automated digital shifts, Gen AI auto-reply rollouts, and other technological changes.
• Support skill diversification across licensed and unlicensed agents to distribute workloads evenly and reduce bottlenecks.
• Support cross-departmental efforts to achieve Objective Key Results, including effective call routing, IVR re-routes, and chatbot deployment.

Requirements

• 2+ years’ experience leading teams in a customer service call center environment.
• Experience with ticketing systems such as Zendesk.
• Customer Service experience from a prior role.
• 1+ years’ experience in the insurance industry with an active Property & Casualty license.
• Self-motivated work ethic with a proven ability to lead a team to high performance standards.
• Ability to engage and collaborate with cross-departmental stakeholders.
• Strong problem-solving skills and analytical proficiencies to develop creative solutions.
• People leadership experience, including identifying and developing talent.
• Strong prioritization, time management, and project-handling skills.
• Experience with ticketing systems and managing email Service Level Agreements.
• Experience with efficiency and performance management.
• Proven change management experience with projects of varying size and impact.
• Experience leading through complex transitions and maintaining engagement during periods of uncertainty.

Preferred Qualifications

• Proven track record of mentoring high-performing team members while fostering a culture of accountability and professional growth.
• Demonstrated ability to navigate organizational shifts and change.
• Hands-on experience with Calabrio (WFM) and Rippit (QA).
• Familiarity with data tools such as Looker, Google Suite, and knowledge bases like Guru.
• Experience leading blended teams consisting of both licensed and unlicensed personnel.

Pay

The annual base salary range for this position is $67,000.00 - $110,600.00. The actual salary will be determined by factors such as scope, complexity, location, skills, education, and experience. Employees are also eligible for performance-based cash incentive awards as part of our comprehensive compensation and benefits program.

Benefits

• Group plan for medical, dental, vision, and prescription drug coverage.
• Short-term disability, long-term disability, and life insurance coverage.
• Participation in the Company’s bonus program.
• 401(k) plan with a 5% employer match.
• Commuter benefits to help cut down on parking and public transit costs.
• 25 days of vacation time plus 10 sick days and 10 company holidays.
• Investment in your learning and development.
• Regular team outings and volunteer opportunities.
• Hybrid working model, offering flexibility to work in a way that suits your job, team, and personal life.