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.
Simply Business is seeking a Director, Business Operations to play a pivotal role in driving strategic execution and operational excellence across the organization. Reporting to the VP of Customer, this individual will serve as a key strategic partner to the US Management Team, helping to create alignment and enable efficient execution of business priorities. The ideal candidate will be a strong strategic thinker with exceptional operational, communication and project management skills who is capable of driving results in a fast-paced environment.
Strategic Planning & Execution:
- Lead the annual and quarterly business planning processes, working closely with leadership and cross-functional teams to define strategic objectives, key initiatives, and resource allocation.
- Champion and manage the OKR process to drive alignment and accountability. Lead regular OKR review meetings, providing insights and facilitating strategic discussions on progress and key challenges. Regularly review resource allocation and provide recommendations to optimize investment and maximize impact.
- Facilitate the preparation of materials and agendas for key leadership meetings and ensure effective follow-up on action items.
- Lead the planning and execution of quarterly leadership offsites.
- Proactively identify areas to improve the operating cadence and make adjustments as the business scales
Communication:
- Facilitate transparent and timely communication across the organization. Work with leadership and internal communications to develop and cascade information on the company’s strategy, key initiatives, and performance results throughout all levels of the organization.
- Create clear and concise presentations and other communication materials for internal stakeholders.
Project Management & Special Projects:
- Oversee project managers to develop project plans, track progress, identify and mitigate risks, and communicate updates to stakeholders.
- Undertake ad-hoc strategic projects and analyses to support leadership decision-making and organizational priorities.
- Monitor industry trends and competitive behavior to identify potential opportunities and help inform strategic planning
Qualifications:
- Bachelor's degree required
- 7+ years of experience in a Chief of Staff, strategy consulting or similar role.
- Experience at a fast-paced, high-growth environment, ideally in insurtech, fintech, or a related industry.
- Strategic Thinker: demonstrated ability to think strategically, analyze complex problems, and drive results.
- Operational Excellence: strong operational skills with a track record of improving processes and driving efficiency. Previous experience implementing and optimizing OKR processes is strongly preferred.
- Team leader: strong people management skills, with the ability to hire, coach, and retain top talent
- Excellent Communicator: superior communication skills, both written and verbal, with the ability to effectively influence and collaborate with stakeholders at all levels. Strong & concise presentation and facilitation skills required.
- Data-Driven: strong analytical and problem-solving skills, with the ability to interpret data, identify trends, and develop actionable insights.
- Project Management: exceptional organizational and project management skills with a track record of successfully managing complex projects from inception to completion.
- Team Player: collaborative mindset and the ability to build strong relationships across the organization. Demonstrated ability to operate successfully in a matrixed and highly cross-functional environment and lead through influence.
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
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.
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Simply Business Teams
What It's Like to Work at Simply Business
About our Teams
Simply Business Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
We offer our SBers more choice and greater flexibility to work in a way that’s best for their particular job, their teams, and their lives.
Typical time on-site:
40 % of the time
