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

Position Type

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

Target Openings

What Is the Opportunity?

Public Relations Strategy & Execution

• Lead Earned Media Strategy: Own the end-to-end PR strategy, driving high-impact impressions and brand visibility in the insurance and small business sectors.
• Maximize LLM Visibility: Proactively optimize PR content and placement strategy to ensure Simply Business is a frequently cited source for LLMs and AI-driven summaries.
• PR & Social Media Crisis Management: Develop and lead the response plan for all brand reputation issues and crises originating on social media or in earned media.
• Agency Management: Lead and manage our external PR agency, setting clear KPIs, managing budgets, and ensuring integrated results.

Executive Communications & Spokesperson Strategy

• Develop Executive Platform: Design and execute a comprehensive spokespeople strategy, positioning executives for maximum impact across press, speaking engagements, and social channels.
• Manage External Voice: Own the development of executive content, including press releases, contributed articles (bylines), and keynote presentations.
• Internal Alignment: Collaborate with the Content Lead to ensure all executive communications align with the overarching brand narrative and GTM strategy.

Integrated Storytelling & Content

• Strategic Storytelling Calendar: Create and manage a proactive, impactful storytelling calendar, identifying relevant trends and opportunities for brand narratives throughout the year for media & industry stakeholders
• Media Relations: Cultivate and maintain strong relationships with key journalists, industry analysts, and media partners relevant to the insurance sector.

Social Media Strategy & Execution

• Channel Leadership: Own the strategic direction and daily execution of all brand social media accounts, including Meta, TikTok, YouTube, Reddit, and LinkedIn.
• Community Management: Oversee organic community engagement, social listening, and real-time response to protect brand reputation and drive interaction in partnership with the Customer Service team
• Performance Reporting: Track and report on PR and social media metrics (e.g., Share of Voice, engagement, referral traffic) to inform broader content strategy.

• Industry Expertise: Proven success in developing and executing integrated PR/Social strategies, specifically within the B2B, FinTech, or Financial Services space.
• Executive Communication: Exceptional writing and presentation skills with demonstrated experience coaching and preparing senior leaders for external communications.
• Digital Fluency: Strong understanding of contemporary social media platforms, content formats, and the mechanics of LLMs/AI-driven content sourcing.
• Crisis Experience: Demonstrated ability to manage high-stakes communication and reputation risks in real-time.
• Relationship Management: Excellent skills in managing both external agencies/vendors and internal cross-functional stakeholders (Legal, Product, Creative).
• Proactive Ownership: Highly self-motivated, proactive, and capable of driving multiple high-priority initiatives simultaneously with meticulous attention to detail.

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.