Director of Go-to-Market (GTM)

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 seeking a dynamic and results-oriented leader to fill the pivotal role of Director of Go-To-Market (GTM). This is an exceptional opportunity to spearhead our marketing efforts, driving impactful strategies that connect with customers and fuel business growth. You will be instrumental in understanding customer needs, developing compelling product positioning and messaging, and launching new products successfully. You will also be responsible for managing a team and fostering cross-functional collaboration. The ideal candidate will have a deep understanding of Go-To-Market strategies in the DTC environment, coupled with significant experience in successful brand and product launches, integrated campaigns, and working within digital/e-commerce organizations.

• GTM Strategy: Develop and execute comprehensive GTM strategies for new and existing insurance products, ensuring alignment with business objectives and market opportunities. This includes defining target audiences, market sizing, and channel strategies.
• Product Positioning and Messaging: Craft clear, concise, and compelling product positioning and messaging that resonates with our target audience. Ensure consistency across all marketing channels and materials.
• Product-Related Content/Assets: Oversee the creation of high-quality product-related content and assets, including website copy, blog posts, brochures, videos, and sales enablement tools.
• Customer Lifecycle Management (CLM) Strategy: Design and implement CLM strategies to enhance customer acquisition, engagement, and retention. Identify ideal customer profiles and key journeys, and develop differentiated programs to enhance their experience and increase conversion.
• Team Leadership: Manage and mentor a GTM Manager and a Customer Lifecycle Manager, providing guidance, support, and professional development opportunities.
• Cross-Functional Collaboration: Work closely and collaborate with Marketing, Insurance Product, and Digital Product organizations to ensure alignment on strategy, execution, and customer experience.
• Performance Measurement: Track and analyze key performance indicators (KPIs) related to GTM and CLM initiatives. Report on results and make data-driven recommendations for optimization.

• 15+ years of experience in GTM, product marketing, or a related field, experience within the insurance or fintech industry is a plus
• Proven track record of developing and executing successful GTM and CLM strategies for DTC, micro-business or consumer-focused brands
• Excellent communication, presentation, and interpersonal skills.
• Analytical and data-driven, with the ability to track and report on key metrics.
• Experience leading and managing teams.
• Ability to thrive in a fast-paced, dynamic startup environment.

• Deep understanding of digital marketing and sales processes.
• Experience with CRM and marketing automation tools.
• Strong project management skills.
• Passion for innovation and customer-centricity.

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/