Senior CopywriterChicago, IL

About Specialty Program Group:

Our goal is to partner with industry-leading specialty businesses to provide them with the ability to achieve their goals and optimize their businesses. Specialty Program Group offers access to capital andinvestment, deep carrier relationships, creative thinking, product development and broad distribution, while allowing our businesses to maintain the essence of what makes them successful. Specialty Program Group delivers leading-edge specialty expertise backed by transformative digital capabilities and sophisticated data and analytics.

About Squaremouth:

Squaremouth was launched in 2003 with the core goals of becoming the best workplace for its employees and the best place for customers to buy travel insurance. In 2014, we utilized our travel insurance expertise to develop and launch Tin Leg, a travel insurance brand with policies designed to address our customer’s most common and pressing travel concerns. Tin Leg quickly became one of the most popular travel insurance providers on and continues to offer some of the most comprehensive products in the travel insurance market.

We’ve grown from a small team to a company of over 50 employees, gaining national and international recognition along the way as one of the best customer service teams and best places to work. Widely recognized for our company culture, we are proud of most recently being named one of the Best Workplaces in America in 2023 by Inc. Magazine!

Continuing to strive toward our goal of being one of the most innovative companies in the field, Squaremouth was acquired in April 2023 by Specialty Program Group (SPG), a leading operator of specialty insurance brokerages and underwriting facilities. Today,, and its multi-award winning customer service team, has helped over 3 million travelers save time and money to find the best travel insurance policy for their trip.

Job Summary

Reporting to the Manager of Brand & Content Strategy, the Senior Copywriter will help translate Squaremouth’s value proposition into powerful, conversion-driving long-form copy across our paid and organic channels.

What You’ll Do

  • Produce high-quality and engaging SEO-optimized content for various platforms, including landing pages, in-depth articles, blog posts, social media, and email campaigns

  • Partner with Marketing leadership to define and execute a robust content strategy and calendar aligned with the travel insurance industry, ensuring it complements the company's overall goals

  • Help develop Squaremouth’s brand positioning and messaging to effectively speak to our target audience

  • Utilize tools such as ClearScope, SEMRush, and Google Analytics to assess the performance of content, identify areas for improvement, and adjust strategies to optimize organic traffic and user engagement

  • Monitor and analyze competitor strategies and adjust content plans accordingly to maintain a competitive edge

  • Identify new marketing opportunities via newsworthy topics, trends, and events that impact travel insurance

  • Provide guidance and mentorship to the junior copywriter, fostering skill development and maintaining a cohesive and effective content team

What We’re Looking For

A portfolio showcasing long-form copy and campaign work is required for consideration for this role .

  • 5+ years of copywriting experience working for an agency, in-house at a brand, or freelance for B2C advertisers, preferably with a focus on direct response style

  • Bachelor’s degree in English, Communications, Journalism or related field

  • Experience generating content for SEO

  • Proficiency in using tools like Surfer AI, ClearScope, and SEMRush

  • A self-starter with excellent written and verbal communication skills

  • Ability to give, accept, and apply feedback

  • Ability to work both within a team and independently effectively in a remote environment

  • Experience writing for industries like insurance, fintech, or education is preferred

Work Location:

This position has remote working opportunities.

Disclosure required under applicable state or municipality regulations: The expected salary range for this position is $70,000 - $80,000 and will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as the specific position’s business line, scope and level. HUB International is proud to offer comprehensive benefit and total compensation packages which could include health/dental/vision/life/disability insurance, FSA, HSA and 401(k) accounts, paid-time-off benefits, and eligible bonuses, equity and commissions for some positions.

Department Marketing

Required Experience: 5-7 years of relevant experience

Required Travel: No Travel Required

Required Education: Bachelor's degree (4-year degree)

HUB International Limited is an equal opportunity and affirmative action employer that does not discriminate on the basis of race/ethnicity, national origin, religion, age, color, sex, sexual orientation, gender identity, disability or veteran's status, or any other characteristic protected by local, state or federal laws, rules or regulations. The EEO is the Law poster and its supplement is available here at

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