At Obie, we don’t just insure properties — we ensure progress. With advanced technology, real-time data, and a vast network of agents and partners, we help real estate investors and landlords get insurance coverage whenever and wherever they need it. Thousands of owners nationwide trust us to be the insurance experts, so they don’t have to be.
Joining our team means embracing a fast-moving environment driven by innovation, collaboration, and constant progress. We learn quickly, iterate often, and celebrate wins together. If you’re passionate about driving change and eager to impact the real estate and insurance market, Obie is the place for you.
Our Chicago based employees are hybrid, and expected to be in office on Tuesdays and Thursdays.
Brief Summary Of Role
As a Senior Marketing Specialist, you will play a key role in executing and optimizing marketing initiatives across Obie’s distribution channels and external marketing efforts. This role blends campaign execution, content development, and strategic support, and will partner closely with the Director and Marketing Manager to drive engagement, support sales growth, and strengthen Obie’s brand presence across agents, partners, and customers.
You’ll operate as a high-impact generalist, contributing across lifecycle marketing, channel marketing, and content strategy, while bringing a strong understanding of performance, messaging, and audience needs.
What You’ll Do
Campaign Strategy and Execution:
- Execute and optimize multi-channel marketing campaigns across email, lifecycle marketing, product marketing, and channel distribution to drive engagement, lead generation, and sales activity
- Support the iteration and rollout of lifecycle and Digital Account Management (DAM) campaigns, including onboarding, engagement, and re-engagement initiatives
- Leverage segmentation, personalization, and A/B testing to continuously improve campaign performance
Channel And Partner Marketing
- Support the development and execution of co-branded marketing initiatives with Agents and Partners
- Assist in building and scaling tiered marketing support packages that equip partners with tools to effectively sell Obie products
- Collaborate with Channel Distribution to execute communications related to product launches, updates, and key business initiatives
Content And External Marketing
- Develop high-quality, marketing-forward content across external channels including blog, website, social media, and sales enablement collateral
- Contribute to SEO-driven content strategy by identifying gaps, trends, and optimization opportunities
- Translate complex insurance and product concepts into clear, compelling messaging for agents, partners, and end customers
- Support content development for product launches, including landing pages, resource hubs, and customer education materials
- Maintain brand voice and consistency across all external-facing communications
Cross-functional Collaboration
- Partner with Product, Engineering and Data, teams to bring marketing initiatives to life
- Support go-to-market efforts for new products and features, ensuring alignment across internal and external messaging
- Collaborate with leadership to refine messaging that reinforces Obie’s value proposition and market positioning
Performance Tracking And Analytics
- Monitor and report on campaign performance, identifying insights and opportunities for optimization
- Support the development and maintenance of dashboards connecting marketing engagement to business outcomes (quotes, binds, revenue)
- Use data to inform content strategy, campaign improvements, and audience targeting
- Leverage AI-powered tools and automation to analyze campaign performance, identify optimization opportunities and enhance targeting, personalization, and content effectiveness
What You’ll Bring
- 5+ years of experience in marketing, including lifecycle/email, digital marketing, or content marketing
- Experience operating as a marketing generalist across campaigns, content, and cross-functional initiatives
- Strong writing and editing skills, with the ability to adapt tone for different audiences (agents, partners, customers)
- Proficiency with marketing and CRM tools (HubSpot, Salesforce or similar)
- Experience with performance marketing concepts including segmentation, testing, and optimization
- Comfort working in a fast-paced, high-growth environment with evolving priorities
- Strong collaboration and communication skills across teams and stakeholders
Preferred But Not Required
- Experience in personal lines insurance industry
- Familiarity with SEO best practices and content optimization
- Experience supporting product launches or go-to-market initiatives
- Exposure to partner/channel marketing strategies
Interview Process
About
At Obie, transparency is core to our interview process. We focus on open communication and a positive experience; no trick questions—just honest conversations about your skills and aspirations. To help you prepare, please familiarize yourself with these resources before moving forward:
- Our company’s blog to learn more about the market we serve and the information our customers value.
- Check out our LinkedIn to see how people interact with our brand and product.
- Press and podcast features like Inc. 5000, TechCrunch, Innovate State, Uncontested Investing Podcast, Insurtech Amplified Podcast
- Meet us and get to know Obie You’ll first talk to Kara on a 30-minute call to determine whether we’re a good fit for one another. You’ll learn more about Obie and have the chance to ask about our company, team, culture, and product.
- Meet the hiring manager Next, you’ll have a 45-minute video interview with the hiring manager, Jessica Smith, to assess your technical skills for the role.
- Complete a Project Exercise This role requires strong strategic, collaboration, and analytical skills, so we’ll ask you to complete a short exercise to flex those muscles. You’ll complete the exercise on your own time, so please be thoughtful and thorough in your response. More details will come when you reach this step!
- Meet the Team Since you’ll be joining a close-knit team, we’ll ask you to meet other people in the company so we get to know each other a bit better