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.
While Obie does offer fully remote opportunities for those outside of Chicagoland, we are only currently hiring in the following states: AZ, CA, DC, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NY, NC, OH, OR, PA, SC, SD, TN, TX, UT, WA, WI
Brief summary of role:
Obie is launching a brand new technology solution into the real estate world. The Account Executive, GTM will be responsible for playing a key role in the go-to-market execution of that tech solution, which assists property managers with their insurance processes. Responsibilities will include, but are not limited to, business development, account management, and product integrations. You will be the first outside hire onto this newly developed team at Obie and play a pivotal role in the success of our new venture.
What you'll do:
- Assist in the business development, account management, and product onboarding for property managers, taking them through the entirety of the sales cycle
- Help shape the strategy to onboard property managers in the most efficient manner, while creating and maintaining deep relationships in order to grow our new tool into a significant revenue driver for Obie
- Establish and maintain productive, professional, and influential relationships with key executives with your accounts, leading to a deep understanding of property manager business organizations
- Build and maintain relationships with key cross-functional business partners within Obie, including but not limited to members of the marketing, data analytics, product and engineering teams, in order to implement strategy to achieve company goals
- Develop a deep understanding of Obie’s tooling & how different property management systems interact with it
- Strategize with existing property managers to create the best possible experience within our tool
- Willingness and ability to host and lead compelling end user demonstrations and overviews of Obie’s offerings to property managers, end users, and educators
What you'll bring:
- 3-5 years of experience in account management, B2B sales, marketing, or partnerships roles, ideally interacting with the property management industry
- Keen ability to manage relationships both externally and internally across multiple stakeholders at varying levels within an organization
- Strategic/critical thinker - ability to leverage tech, tools, and resources. Demonstrates the ability to tackle a project or problem without all the context
- Data driven - you love utilizing data to create insights and inform strategy
- Excellent communication skills and the ability to in time explain complex insurance concepts in a clear and concise manner
- Passion for early-stage startups and/or high growth environments
- Able to deal well with ambiguity and maintain composure in complex situations
Bonus points:
- Chicago based or the ability to come into the Chicago office as needed
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:
- 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, Brian, to assess your technical skills for the role. - Complete a Project Exercise
This role requires a strong understanding of how to manage the sales cycle of a new SaaS tool from initial outreach through account management. You will be tasked with putting together a short deliverable on the merit of Obie’s new product and how it can have the maximum impact for property managers. You should be ready to read a quick explanation of the product and do moderate research on the property management space to provide your perspective on how to bring this to market in the most effective way. 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.
More about 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:
- Competitive salary
- Flexible time off with an encouraged minimum time away to support a healthy work-life balance
- 12 weeks of Paid Parental Leave
- Great health, dental and vision coverage
- Life Insurance
- Flexible Spending & Health Savings Accounts
- Stock Options
- 401k match
- Pet Insurance Reimbursement
- Health and wellness benefit
- Equipment budget - everything you need to do your best work
- Professional development support
- Summer hours