Global Head of Talent Management (Boston)

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.

We are looking for a Head of Talent Management to join our team and lead our global talent management strategy to accelerate business and employee growth. This leader will have a chance to shape the experience and strategic plan across the talent lifecycle from EVP and talent acquisition to development for our employees and leaders as well as career development and talent management. This role will report directly to the Global Chief People Officer and serve as a member of the Global People Leadership team while building and leading a team of talented SBers.

• Living our values: We're big on our values, and you'll make sure they're baked into everything we do with our people.
• Building our employer brand: You'll help us tell the story of why Simply Business is a fantastic place to work, attracting top talent.
• Attracting top talent: You’ll ensure we are able to hire the right talent to fuel Simply Business’ growth.
• Making growth happen: You'll lead the charge on performance development, making sure everyone knows where they stand, where they're going and how to get there. Think clear goals, helpful feedback, and exciting growth opportunities.
• Developing our leaders: You'll create programs that develop and enable our managers to be even better and help grow industry best leaders
• Fueling careers: From killer onboarding to ongoing learning, you'll design and deliver opportunities that help everyone at SB grow and thrive.
• Being a trusted partner: You'll work closely with our leaders to understand their needs and build talent solutions that make a real difference.
• Staying ahead of the curve: You'll bring fresh ideas and best practices to the table, always looking for ways to improve how we do things.
• Making it happen globally: You'll build and lead a team, ensuring our talent strategy works brilliantly across all our locations.
• Using smart tools: You'll know how to leverage tech to make our talent processes even better.

• Significant experience (8-10+ years) in talent management and learning & development, with a track record of scaling global programs and leading teams (5+ years).
• A passion for understanding the business and how talent can drive our success.
• Top-notch communication skills – you can talk to anyone and get your ideas across clearly.
• You're great at juggling multiple projects in a fast-paced environment and making things happen.
• You're a natural collaborator and love building strong relationships.
• Experience with hybrid workforces is a plus.
• Ideally, you've worked in tech or similar fast-moving industries.
• You're strategic, you're a leader, and you know how to get results.
• You're all about using data to make smart decisions and aren't afraid of new tech like AI.
• You're a pro at designing clear and scalable talent processes.
• You get how to work with different cultures and navigate change.
• You're passionate about creating a diverse and inclusive workplace.

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

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/