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Licensed Supervisor, Customer Self-Service

Boston, MABoston Customer Solutions CenterPermanent (Full-Time)Boston Customer Solutions Center

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Simply Business is more than our name. It's how we approach insurance: Make it clear. Make it simple. Make it affordable. By combining exceptional talent, technology, data, and knowledge, Simply Business is the go-to online insurance brokerage that protects small businesses and the entrepreneurs who work hard to build them. 

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.

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 purchasing the right coverage of small business insurance. 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 a small team of unlicensed Service Agents for a small team of Insurance Producers.

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.

Service Supervisor, you will:

  • Lead the day-to-day performance of a team of Service staff
  • Motivate and coach your team to meet and exceed expected performance levels
  • Monitor and evaluate individual and team performance; assist in the development of individual and team performance measures
  • Understand individual development needs and support said needs through effective coaching and guidance
  • Partner with the quality and service support team to ensure compliance requirements are met
  • Collaborate with other members of the CSC and stakeholders to implement initiatives to increase team performance, quality, efficiency and engagement
  • Ensure company processes and procedures are adhered to by team and individuals

What we are looking for:

  • 2+ years’ experience leading teams in a call center/service environment
  • Must have experience with ticketing systems such as Zendesk
  • Must have Customer Service experience from a prior role
  • 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
  • Experience with Google Suite, Looker,  and Adobe 
  • Proven past change management experience with projects varying in size and impact 
What are the benefits?

Here are some of the great benefits and perks that come from being a Simply Business employee:
• A salary that reflects your experience, our pay policy, and the market we’re in from your first day
• 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
• Annual company trip, regular outings, and volunteer opportunities 
• An awesome WeWork office with cold brew coffee and other beverages on tap, local pop-up events, and more 

Simply Business is an equal opportunity employer. We're committed to welcoming and helping to grow employees within an inclusive & diverse culture. And that commitment starts with our interview process. 

Once you apply, your info will be reviewed in a committee with employees from different levels, teams, 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!

Want more info on working at Simply Business? Check out our careers page: 

What's going on with work from home and return to the office?

More and more, people are talking about going back to the workplace and the new normal. At Simply Business, we’re thinking of it as a Better Normal. That means offering our SBers more choice and greater flexibility to work in a way that’s best for their particular job, their teams, and their lives.

We’re shifting to a hybrid working model, so we’ll have employees working virtually and in the office at any given time.

We’re also aware there are times when working together in person is the best way to get things done. We expect our SBers to connect in their hubs (that’s what we call our offices) most likely 4 times a month. That said, there’s no one-size-fits-all solution, so we expect all SBers and their teams will find the operating rhythm that works best for them.

If you’re wondering what it might be like for you at Simply Business, our Talent Acquisition is happy to answer any questions. In fact for them, it’s perfectly normal.

Most of our interviews will still take place over Zoom (however, depending on the role, there may be the opportunity/expectation to meet members of the team in-person).  If it looks like you could be a good fit for the role, we’ll ask you to interview on Zoom – 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]. Similarly, 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.
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*Harborway Insurance policies are underwritten by Spinnaker Insurance Company and reinsured by Munich Re, an A+ (Superior) rated insurance carrier by AM Best. Harborway Insurance is a brand name of Harborway Insurance Agency, LLC, a licensed insurance producer in all 50 states and the District of Columbia. California license #6004217.

© Copyright 2023 Simply Business. All Rights Reserved. Simply Business, LLC is a licensed insurance producer in all U.S. States and the District of Columbia. Simply Business has its registered office at Simply Business, 1 Beacon Street, 15th Floor, Boston, MA, 02108. In the state of California, we operate under the name Simply Business Insurance Agency, Inc., License #0M20593. In the state of New York we operate under the name Simply Business Insurance Agency. In the state of Texas we operate under the name, U.S. Simply Business, Inc. For more information, please refer to our Privacy Policy and Terms & Conditions.