Simply Business

Head Of Internal Communications

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Easy Apply

Boston, MA

Hybrid

Fintech • Information Technology • Insurance • Software

We Protect The Small Businesses You Love.

The Role

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.

Ready to make a real impact? At Simply Business, we're looking for a visionary Internal Communications leader to shape how we connect and inspire our 1,000-strong team across two markets. You'll build out our internal communications capabilities, own our communications strategy and narrative as well as playing a pivotal role in guiding our people through the next chapter of growth. As a key partner to our Global CEO and Group Executive Team, you'll develop a deep understanding of our business and culture, ensuring our communications reflect the best of who we are while adapting to diverse needs. You'll define core communication principles, provide strategic counsel to leaders and constantly seek new ways to keep our people informed, engaged, and connected.

As our Head Of Internal Communications, you’ll:

Create and deliver the global internal communications strategy for Simply Business.
Own the evolution of our narrative while establishing new levels of quality communications to build high engagement of colleagues based in the US and UK.
Drive clear understanding of business strategy and be a key contributor and custodian of our award-winning culture through the coordination of internal communication efforts.
Directly help people across the business understand their role in executing our strategy and driving performance, creating buy-in for our purpose and feeling motivated about our future

We’re looking for someone who is:

An experienced, data-driven communications leader with an expert understanding of how communications influence behaviors
Able to demonstrate exceptional written and storytelling skills - a proven expert in simplifying complex information and communicating in the authentic tone of different leaders
Ability to guide, challenge and direct the Global CEO on all their communications in partnering with and influencing key stakeholders including market CEOs and Chief People Officer - agreeing comms priorities that will drive the results that matter
A proactive self-starter, equally happy defining strategy as when hands on delivering comms
Able to positively impact employee engagement across a global organisation to ultimately drive business results

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/

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The Company

HQ: Boston, MA

1,100 Employees

Year Founded: 2005

What We Do

Simply Business is dedicated to making small business insurance simple and accessible. Our robust digital marketplace allows small business owners to find and buy the insurance they need online, matching them with coverage from multiple top insurers to offer choice, transparency, and value.

We have nearly 20 years of experience supporting small businesses, with over 1 million customers worldwide. Founded in the U.K. in 2005, Simply Business launched its U.S. operations in 2017 and today employs over 1,000 people across offices in London and Northampton in the U.K., and in Boston and Atlanta in the U.S.Simply Business is more than our name. It’s how we approach small business insurance.

Why Work With Us

Here at Simply Business we have five core values that we uphold in everything that we do: Learning, Empowerment, Authenticity, Pioneering, and Simplicity. Utilizing these values and embedding them into our culture makes SB a unique and great place to work, a place where every person is valued, a place where we get things done and have fun doing so.