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.
Simply Business is seeking a strategic and results-oriented Director of our Customer Solutions Center (CSC). You will lead a team of 70+ across Sales, Service, Quality, and Operations to support our customers with their business insurance needs. As the leader of the CSC, you will set the vision and lead the team in bringing that vision to life. Reporting to the VP, Customer, you will be responsible for the strategic planning and execution of all CSC operations. You are excited about establishing a performance-oriented culture, driving the team towards results, and delivering a top-notch customer experience.
As a Director of Customer Solutions Center, you will:
Drive business results:
- Manage performance across your Sales and Service teams to meet or exceed revenue, cost, efficiency, and quality targets.
- Analyze KPIs, manage to OKRs, and proactively identify areas for improvement.
- Lead initiatives to introduce automation and digitization where possible.
- Seek out technology and innovative solutions to bolster efficiency and streamline operations.
- Identify opportunities for continuous improvement as the business scales
Lead a high-performing team:
- Recruit, lead, and develop a high-performing team.
- Partner closely with Talent Acquisition in attracting high-caliber sales and service talent.
- Work closely with the CSC Training team to effectively onboard new talent to achieve strong performance.
- Motivate and inspire your team to achieve or exceed its goals while maintaining a great culture and fostering strong employee engagement.
- Work closely with our workforce planner to anticipate and plan for staffing needs as the business evolves.
- Proven track record of leading through successful change management
Deliver an excellent customer experience
- Collaborate with marketing, product, and other stakeholders to support new initiatives and ensure a seamless customer experience
- Ensure compliance with regulatory standards and company policies/processes
What we are looking for:
- Bachelors Degree Required
- Minimum of 5 years of Contact Center management or similar experience
- Property & Casualty license preferred or to be obtained within 90 days of employment
- Proven track record of driving team success, managing to metrics, and ensuring customer satisfaction.
- Experience leading remote/hybrid teams a plus
- Passion for developing people and leading high-performing teams
- Ability to influence cross-functionally to drive initiatives forward
- Monthly travel to Boston HQ required
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. And that commitment starts with our interview process.
Once you apply, your info will be reviewed by a team with a mix of levels and experiences. We pride ourselves on fostering a sense of community, which is only made stronger by each individual at SB, so you’ll have the opportunity to meet a variety of people throughout the process. Get excited!
Most of our first round interviews will take place over Zoom. In subsequent interviews, there may be an opportunity/expectation to meet team members in person.
If it looks like you could be a good fit for the role, we’ll ask you to interview on Zoom first regardless – you’ll need WiFi and a laptop, or a 4G-enabled smartphone. If you don’t have access to either of these, or you need support with your application, get in touch with us at [email protected].
Please email us with any questions or if you want to pause your application for a bit – we’ll be happy to keep you updated on future opportunities like the one above. Want more info on working at Simply Business? Check out our careers page: simplybusiness.com/careers/
