Content Director


About Us:

A pioneer in insurance technology, Insureon operates the largest online insurance marketplace for small businesses in the U.S. Our proprietary technology platform enables business owners to easily compare and purchase the insurance they need. We also license this platform to select industry participants who are looking to more effectively service their own clients. We are integrated with every major U.S. carrier, manage over ~$400M in premium annually and are licensed in all 50 states. For more information, visit

The company employs approximately 150 people nationally, with its corporate location in the heart of the financial district in the Chicago Loop.

We place a high value on having fun at work, personal and company integrity and teamwork, and we believe our success is truly a team sport. We foster a service mentality inside and outside our company and our fast-paced team is driven by results and is energetic about servicing our clients.

This role is based in our Chicago headquarters (and has the ability to work remotely in the near-term due to Covid-19)

Position Details

Content Director
Chicago Illinois
Chicago, IL

What You'll Do:

The Content Director will lead the Content team of an online commercial insurance marketplace that relies on exceptional, accurate, and compelling content to generate new business and retain small business customers. This function shares responsibility for achieving the business’s top-of-funnel goals, monitoring KPIs and analytics, and creating and adjusting plans accordingly. We’re seeking a results-oriented leader who will take ownership for Insureon’s content to educate small business owners, convert prospects into customers, retain and upsell existing customers, and increase brand recognition.

The Content Director sets the content strategy and team’s priorities, ensuring both are aligned to business goals. You’ll oversee and assist the Content team with execution while continually raising quality standards. You will define editorial standards and refine messaging to ensure content resonates with small business owners across many professions and industries at different stages of their customer journeys. This position involves collaboration with leaders across the organization, particularly with the SEO and Analytics teams, and works closely with members of the Senior Leadership Team.

We prefer local candidates but will consider remote applicants.

Responsibilities – The “Day-to-Day;”

  • Synthesize team goals and small business owners’ needs to create content plans, allocate resources, and measure campaign and content success. 
  • Partner with SEO and leaders throughout the company to determine content priorities anchored to business goals, SEO trends, and Customer Experience (CX). 
  • Monitor KPIs and analytics to ensure session, conversion, and engagement goals are on track, and adjust plans accordingly. 
  • Stay abreast on content strategy and marketing trends and best practices, regularly testing new approaches and delivery methods. 
  • Target and develop content partnerships with publishers and organizations that service our small business audience and can increase our brand awareness. 
  • Lead A/B testing strategy for content initiatives and partner with SEO, Product, and UX teams on larger-scale tests. 
  • Build relationships with customers to understand their insurance and small business needs, inform content planning, include their perspective and testimonials. 
  • Advocate for website, blog, and digital experience enhancements for a better content experience, partnering with Product Management to define scope and prioritization. 
  • Manage Content team’s day-to-day budget, including in-house and outside spend. 
  • Drive original-research content that captures customers’ and the media’s attention. 
  • Provide regular coaching to Content team members. 
  • Assist Human Resources and Senior Leadership Team with corporate messaging and public relations needs. 
  • Refine and codify editorial guidelines, including voice and tone, aligning them to the needs of customer personas and jobs to be done (JTBDs).
  • Bachelor’s degree in a content-related field (Marketing, Journalism, English, etc.) desired; master’s preferred 
  • Minimum of 7 years of relevant experience in an in-house role required 
  • Minimum of 3 years of experience leading a team of in-house and freelance writers required 
  • Experience with enterprise-class CMSes preferred; Sitecore experience a plus 
  • Expertise in AP Style and developing in-house style guides 
  • Deep understanding of interaction between SEO and content required 
  • Proven track record of guiding others to create compelling content that integrates targeted keywords and readability best practices 
  • Knowledgeable of best practices for web, mobile, and social media content 
  • Ability to manage multiple priorities and deliver in a fast-paced, dynamic environment

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