Senior People Operations Specialist
Boston, MA
People - People Ops – People Operations /
Contract /
Hybrid
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.
The Senior People Operations Specialist is a key contributor to the People Operations team, responsible for managing complex HR processes and providing strategic support to the organization. This role requires a deep understanding of HR best practices, and a proactive approach to problem-solving. The ideal candidate will have extensive experience in all aspects of the employee lifecycle and a proven track record of driving process improvements and enhancing the employee experience.
9 month contract
Key Responsibilities:
- Identify opportunities to streamline and automate People Operations processes globally to improve efficiency and data accuracy.
- Oversee complex employee relations issues, partnering with legal counsel when necessary and providing guidance and recommendations to managers and employees.
- Administer and manage advanced leave cases, including disability claims, accommodations, and complex FMLA scenarios.
- Act as a subject matter expert for the HRIS, ensuring data integrity, security, and optimal system utilization.
- Maintain complex HR dashboards and reports to provide data-driven insights to leadership on trends in turnover, engagement, and other key metrics.
- Ensure the organization's HR practices are in full compliance with all federal, state, and local employment laws and regulations.
- Ability to leverage HRIS systems (i.e., Workday, Dayforce, etc.) to process transactions, run reports, identify trends and insights and ensure data integrity
Qualifications
- Education: Bachelor's degree in Human Resources, Business Administration, or a related field
- Experience: Progressive experience in an HR or People Operations role
- Skills:
- Comprehensive knowledge of HR principles, employment laws, and best practices.
- Advanced proficiency with HRIS systems and data analytics tools.
- Proven experience in managing complex employee relations cases and conflict resolution.
- Exceptional project management and organizational skills.
- Strong analytical skills with the ability to interpret data and present actionable insights.
- Excellent communication, negotiation, and interpersonal skills.
- Ability to work independently, prioritize tasks, and manage multiple projects simultaneously.
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 uscareers@simplybusiness.com.
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/
