Simply Business - Insurance for your business

  • Business insurance

    Business insurance covers

  • Support
  • Claims
  • Sign In
Call Us0333 0146 683
Our opening hours
Current vacancies

Legal Counsel

Boston, MALegalPermanent (Full-Time)Legal

Apply now
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 Simply Business, our major competitive advantage is our people. As we continue to scale the business, we are looking for Legal Counsel focused on regulatory compliance to join our growing US team. In this role you will be responsible for handling a wide range of insurance regulatory and compliance matters in a quickly evolving and highly regulated industry. 

This role will report to the General Counsel and be a thought leader and business partner on all things regulatory and compliance. In addition to providing subject matter expertise and collaborating with stakeholders across the business, you will have a practical approach, business mindset and strong interpersonal skills. 

Key Responsibilities:

  • Primarily advise on a broad array of insurance regulatory issues and compliance matters, including licensing requirements, product development, customer notifications and state filing requirements in both the admitted and non-admitted markets
  • Desire to get involved in a wide range of legal issues, including reviewing commercial agreements and marketing materials, and working on intellectual property, privacy and other corporate matters as needed.
  • Ensure compliance with applicable state and federal laws, regulations, directives and rulings.
  • Perform compliance oversight, reporting and suggested remedial actions for breaches and/or errors that have compliance or regulatory impact
  • Assist with the development, implementation and/or enhancement of compliance programs and initiatives, including corporate policies, controls and monitoring, and defining and creating supporting documentation to demonstrate compliance
  • Conduct risk assessments to identify areas of risk and potential areas of compliance vulnerability
  • Monitor, interpret, and disseminate relevant information on applicable insurance laws and regulations including proactively reviewing ongoing development of new laws and regulations.
  • Assist with employee training and education on legal and compliance matters


  • J.D. from an accredited law school
  • Admitted to practice law and in good standing with at least one state bar
  • 5-8 years of relevant experience in regulatory compliance (property and casualty preferred)
  • Relevant legal compliance experience with a major law firm, in-house legal/compliance department or government entity/regulator
  • Ability to provide guidance and advice on key compliance risk areas, such as anti-corruption and anti-bribery, OFAC, sanctions laws, other relevant risk areas
  • Excellent interpersonal skills with a high level of professional and personal integrity.
  • Ability to be creative and practical with a focus on innovation in a highly regulated industry
  • Proven ability to develop strong relationships with and earn the respect and trust of key stakeholders.
  • Dynamic communication and interpersonal skills with ability to build strong cross functional relationships.
  • Desire to tackle a broad range of issues in a fast paced and rapidly scaling environment, and Act with a high level of personal integrity, professionalism, intellectual curiosity and willingness to grow.
  • Excellent written and oral communication skills.
  • Ability to explain legal issues clearly, concisely and persuasively.
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 3% 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
• 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 once every few weeks. 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.
Apply now

Keep up to date with Simply Business. Subscribe to our monthly newsletter and follow us on social media.

Subscribe to our newsletter


Public liability insuranceBusiness insuranceLandlord insuranceTradesman insuranceCharity insuranceNot for profit insuranceRestaurant insuranceCommercial van insuranceInsurers


6th Floor99 Gresham StreetLondonEC2V 7NG

Sol House29 St Katherine's StreetNorthamptonNN1 2QZ

© Copyright 2022 Simply Business. All Rights Reserved. Simply Business is a trading name of Xbridge Limited which is authorised and regulated by the Financial Conduct Authority (Financial Services Registration No: 313348). Xbridge Limited (No: 3967717) has its registered office at 6th Floor, 99 Gresham Street, London, EC2V 7NG.