Director, Brand and Go to Market

Location: MA - Boston · Hybrid

Who Are We?

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.

Job Category

Marketing

Position Type

Permanent

Compensation Overview

The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.

Salary Range

$146,400.00 - $241,600.00

Target Openings

1

What Is the Opportunity?

We are seeking an experienced Marketing leader who has a passion for introducing new brands and categories to the market, as we aim to increase brand awareness of Simply Business in the US. The successful candidate will have a proven track record in brand strategy, Go-to-Market, PR, and creative management and will thrive in a fast-paced, high growth environment.

• Develop and execute a comprehensive brand strategy to elevate our brand in the market and drive business results. Oversee brand positioning, messaging, and identity across all channels and touchpoints.
• Define compelling value propositions and messaging frameworks that inform and elevate our overall go-to-market strategy. Regularly test and iterate on messaging throughout the funnel to optimize creative performance.
• Lead our design team in creating compelling and innovative campaigns that capture our brand essence and drive performance for the business.
• Partner with the Growth Marketing team to design and implement integrated marketing campaigns that drive brand awareness, consideration and loyalty. Identify and activate strategic partnerships opportunities to improve brand visibility and credibility.
• Manage public relations and external communications efforts to build and maintain a positive brand reputation and media presence. Develop our social media strategy and drive visibility across organic channels and LLM’s.
• Develop messaging and high-impact assets for our partnership channel to accelerate growth and adoption.
• Develop and execute a comprehensive content strategy focused on driving SEO performance and maximizing visibility across LLMs. Craft authoritative, high-value content that enhances organic search rankings, establishes brand authority, and engages target audiences to drive customer acquisition.
• Develop and manage the brand marketing and creative budget, ensuring efficient and effective allocation of resources.
• Mentor, develop, and manage the performance of the Brand & GTM marketing team, fostering a collaborative and high-performing environment. Partner with stakeholders across marketing and cross-functional teams to drive initiatives forward.
• Oversee relationships with external agencies, freelancer networks, and other vendors to ensure seamless execution of brand and creative projects.

• Proven track record of developing and executing successful brand strategies and campaigns.
• 10+ years of experience in Brand/Product marketing, preferably at a startup or growth stage digital business. Experience in the insurtech / fintech industry is a plus.
• Exceptional creative vision and ability to translate brand strategy into compelling creative content.
• Takes a data-driven approach to analyzing the impact of brand and shaping brand strategy
• Hands-on leader with ability to lead and inspire a team while also rolling up their sleeves to help execute initiatives.
• Experience evaluating and leveraging emerging AI tools.
• Superior communication skills, both written and verbal, with the ability to effectively influence and collaborate with stakeholders at all levels. Strong & concise presentation skills required.
• A strong collaborator, with demonstrated ability to operate successfully in a matrixed and highly cross-functional environment and lead through influence.

What Is in It for You?

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.

Employment Practices

Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture.