Licensed Service Supervisor

Who Are We?

Simply Business is a digital insurance brokerage that specializes in one thing: protecting the businesses our customers are working hard to build. We’re doing this by simplifying the insurance-buying process for all small businesses, blending together a combination of technology, data, and insurance knowledge. Our proprietary technology platform allows small business owners to easily search and compare quotes from over 20 top-rated insurance providers, customize their coverage, and purchase and access their policies – all online.

Founded in the UK in 2005, Simply Business is an insurtech pioneer with nearly 20 years of experience supporting small businesses. Simply Business is passionate about building an outstanding product for our customers – one that empowers their entrepreneurial spirits.

More importantly, we’re doing it all while taking care of our people. We’ve consistently been named a best place to work, including most recently ranking in Built In’s 2025 Best Companies to Work for in the US (Top 100), and Best Places to Work in Boston.

We want team members who have the drive to challenge boundaries. If you’re smart and passionate about delivering brilliant customer experiences, we’d love to hear from you.

What Is the Opportunity?

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 by guiding them through servicing the right coverage for small business owners. As we continue to grow in size, we are seeking passionate, enthusiastic, and innovative individuals to join the CSC as a hands-on supervisor for our team of Licensed Service Agents.

Our CSC Supervisors should be extraordinary leaders who will work collaboratively with their team while inspiring and empowering each individual to achieve their best. We are seeking highly-engaged leaders who take initiatives, are accountable, and can provide coaching and mentorship to their team.

• 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 help identify performance gaps
• Lead, monitor, motivate, and evaluate the day-to-day performance at team and individual level. Ensure company processes and procedures are adhered to by team and individuals
• Partner with the quality, operations, product and service support team to ensure compliance requirements are met
• Collaborate cross-functionally to align day-to-day 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 for automated servicing
• Support skill diversification across both licensed and unlicensed agents to distribute workloads evenly and reduce bottlenecks.
• Support cross-departmental efforts to overall Objective Key Results including effective call routing, IVR re-routes, and chatbot deployment.

Required Skills:

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

Preferred Experience:

• Proven track record of mentoring high-performing team members while fostering a culture of accountability and professional growth
• Demonstrated the ability to navigate organizational shifts and change
• Hands-on experience navigating 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.

What Is in It for You?

Here are some of the great benefits and perks that come from being a Simply Business employee:

• 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-Participation in 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.
• A genuine investment in your learning and development-Regular team outings and volunteer opportunities.
• An awesome office space.

Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture.

Pay: $66,996.21 - $80,683.61 per year

Work Location: Remote