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.
The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.
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.
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.
A hybrid working model, giving our employees great choice and flexibility to work in a way that’s best for their particular job, their teams, and their lives.
Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture.