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
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
Moving Forward with Obie
Obie is leading the future of real estate investment protection, securing over $25 billion in coverage for thousands of policyholders nationwide. Backed by $39 million in funding and recognized as a top workplace by Built In and Inc., we’re committed to driving progress for our customers and team. Through advanced digital tools, a trusted agent network, and strategic partnerships, Obie provides real estate investors the insurance coverage they need to move forward confidently.
Obie has you Covered
Being in the insurance industry, we understand the importance of comprehensive benefits for you and your family. These are just some of the benefits and perks we provide:
- Comprehensive health, dental, vision and life insurance
- Flexible paid time off
- Retirement savings plan with company match
Obie values transparency and data driven decision making, enabling us to have a consistent and equitable approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly check our salary ranges against other venture backed companies and startups within our industry. We've provided the full base salary range for this role below, but please note that we typically target the mid point of the salary range to allow room for growth within the role. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.
During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.
Top Skills
What We Do
Obie is the leading investment property insurance platform, providing landlords, real estate investors, and partners with instant quotes, tailored coverage, and an entirely digital experience. Backed by proprietary technology, Obie simplifies insurance so deals can close faster and investors can move forward with confidence. Whether they’re obtaining a quote in under 5 minutes on our website, via a partner platform, or through an independent agent partner, Obie has real estate investors covered. Since 2017, Obie has been on a mission to simplify, streamline, and enhance landlord insurance for the 17 million real estate investors and landlords across the United States. With expert-backed coverage, intuitive tools, and embedded technology, Obie delivers fast, reliable insurance solutions designed to fit how real estate professionals work today. Instead of waiting weeks to satisfy insurance requirements or to find the right coverage on a rental, investors and landlords of 1-4 unit properties can obtain instantly bindable quotes thanks to the Obie instant quote process. This offering goes beyond Obie’s own web presence by integrating into partner websites, platforms, and processes. Obie is more than a pioneer; it is the only company to offer a truly seamless embedded insurance process to investors. The Obie instant quote process leverages data enrichment, applying unique algorithms to up to 1,000 data points obtained through multiple databases. This methodology allows Obie to more accurately assess risk, making underwriting faster and more efficient. In doing so, Obie’s technology not only drives faster quote generation, but also ensures that each quote meets the distinct needs of each property and investor. The result is a superior customer experience that confirms Obie’s position as the leading digital provider of insurance for real estate investors. With thousands of policyholders nationwide and $60 billion in coverage secured, Obie is already transforming how real estate investors protect their assets—and we’re just getting started. Backed by $39 million in funding from industry giants like Battery Ventures and Thomvest Ventures, we’re rapidly growing and continually adapting to meet the unique needs of our customers. Whether through our advanced digital tools, trusted agent network, or strategic partnerships, Obie sets a new standard in real estate investment insurance, ensuring those we serve move forward.
Why Work With Us
Joining our team means embracing a fast-moving environment driven by innovation, collaboration, and constant progress. We learn quickly, iterate often, embrace curiosity, 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.
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