Obie

Assist customers in retaining policies through empathetic communication and objection handling, and educate them on coverage options. | Requires 4+ years in insurance, 2+ years in customer retention roles, and insurance licensing, with strong communication and de-escalation skills. | Brief Summary of Role Help customers stay protected when it matters most. We’re looking for an experienced insurance professional who thrives in high-stakes conversations, knows how to calm challenging situations, and can confidently guide customers to the right decision—even when cancellation is on the table. This role is ideal for someone with a strong background in customer advocacy, policy retention, and objection handling who wants to make a real impact on both customer outcomes and business results. Those successful in this role have a strong sense of intellectual curiosity, the ability to think critically, and a desire to help others solve problems. They are self motivated with a strong ability to work autonomously, as you'll be expected to succeed without heavy direction. The hours for this role will fall within 10:00 AM - 8:00 PM EST, Monday - Friday. It is an 8-1/2 work day with 30 minutes for lunch. What You'll Do • Partner directly with existing customers to retain policies and accounts through empathetic communication, education, and expert objection handling • Confidently navigate rate increases, coverage questions, life changes, and cancellation requests, turning risk into opportunity • Educate customers on the value of their coverage, available programs, and alternative solutions to prevent unnecessary lapses or cancellations • Resolve customer requests quickly and accurately through Salesforce cases, inbound calls, and digital channels • Deliver a top-tier customer experience on every interaction—especially during emotionally charged or time-sensitive situations • Collaborate with carrier partners, referral sources, and internal teams to ensure the best possible outcomes for customers • Follow established processes for customer follow-up, documentation, and data integrity • Contribute to a culture built on motivation, accountability, and continuous improvement • Take on additional responsibilities as business needs evolve What You'll Bring • 4+ years of experience working in the insurance industry, with a strong preference for Property & Casualty and homeowners insurance exposure • 2+ years in a customer service role, ideally supporting retention, renewals, cancellations, or escalations • Proven ability to de-escalate difficult conversations, handle objections, and retain customer accounts • High ownership mentality—you proactively seek answers, leverage resources, and solve problems end-to-end • Strong time-management skills with the ability to prioritize competing demands in a fast-paced environment • Comfort operating in ambiguity—you adapt quickly as processes, tools, and customer needs evolve • Exceptional attention to detail when handling policies, coverage data, and customer documentation • Ability to work both independently and collaboratively in a fully virtual environment • Clear, confident verbal and written communication skills that build trust and credibility with customers • Experience using Salesforce, CRM platforms, Excel, and Google Workspace (or similar systems) • Personal standard for excellence: strong process orientation and interest in finding better ways to do things. • An active Property & Casualty insurance license is required before starting. 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 Mary 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. • Complete a Project Exercise This role requires strong communication and analytical skills, so we’ll ask you to complete a short exercise. You can take your time and use the resources available. We’ll assess your problem-solving abilities, writing skills, empathy, demeanor, and organization skills. More details will come when you reach this step! • Meet the hiring manager Next, you'll have a 1 hour video interview with the hiring managers, Chrissy Palmer and Ben Sax, to assess your technical skills for the role. • 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.

Perform data quality checks, reconciliations, and automate data quality processes, supporting financial and insurance data management. | 2+ years in data analytics, familiarity with accounting principles, insurance experience, strong SQL and Python skills, and excellent communication. | Brief Summary of Role We are seeking an individual to join the Data Analytics team at Obie. Those successful in this role will have data analytics experience, finance and accounting reporting skills, and experience in P&C insurance. Those successful will also have stellar interpersonal skills and be comfortable communicating both within the data analytics team and with leadership across the company. What you'll Do Perform daily data quality checks of all critical data sets and recommend required changes to the data (and potentially systems creating the data) Perform reconciliations between different critical data sets that contain similar data to identify and explain any discrepancies to VP of Finance Perform daily updates to our external reporting datasets to ensure data is accurate and complete Answer data quality/reconciliation questions from other departments and produce findings to the data team and inquiring party Lead data team automations, such as the implementation of data quality tools/automated data quality checks Assist with building simple dashboards / reporting within our Business Intelligence / Data Visualization tool Assist with the implementation of data quality tools / automated data quality checks What you'll Bring 2+ years of experience in data analytics, or an adjacent field Familiarity with accounting principles and financial reporting required Insurance experience required Strong SQL experience required Python experience required Strong interpersonal and communication skills Strong time management skills and ability to manage competing priorities 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 Skylar 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, Sam Isken, to assess your technical skills for the role. Complete a Project Exercise This role requires strong planning, collaboration, communication, and analytical skills, so we’ll ask you to complete a short exercise to flex those muscles. You can take your time and use the resources available. We’ll assess your problem-solving abilities, writing skills, empathy, demeanor, and how well you apply key data analytics principles. 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 starting base salary range for this role below. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc. $78,000 - $104,000 USD per year (US) During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.

The analyst will help manage compliance operations for surplus lines insurance, ensuring adherence to state regulations. They will also complete filings, remit payments, and assist with compliance-related inquiries across the organization. | Candidates should have at least 2 years of experience in P&C insurance compliance and knowledge of surplus lines regulations. Proficiency in various software tools and strong communication skills are essential. | Brief Summary of Role Obie is looking for a bright, hard-working individual to assist with the compliance needs of our surplus lines insurance operations. This person will help maintain and manage procedures that ensure regulatory and legal compliance in accordance with applicable state statutes and regulations. Those successful in this role will have knowledge and experience in the surplus lines insurance space with passions for leading by example and creating new and different solutions while leveraging technology. Additionally, you’ll be self-motivated and directed. An ability to collaborate is a must, but you will be autonomous and expected to succeed without heavy direction. What you'll Do Help manage the diligent effort operation and ensure its compliance with each respective state & insurance program Complete surplus lines filings; ensure they are compliant and on time Work with accounting to remit tax and fee payments to the state Assist in compliance needs as it pertains to the insurance operation including but not limited to monitoring, auditing, investigating, and updating policy lifecycle operations and procedures Maintain accurate compliance resources, by state, for underwriting, operations & insurance product Advise on ad-hoc compliance questions from different business units throughout the organization Provide input to operational projects as it pertains to by-state regulatory compliance What you'll Bring Knowledge of surplus lines laws & regulations 2+ years of P&C insurance compliance experience Surplus lines operations experience Firm grasp on regulatory needs and applicable resources Experience and comfort using a variety of software tools from Excel and G Suite, to policy management and customer relationship management software Excellent verbal and written communication skills Fearlessness and adaptability in a fast-moving, ever-changing environment and ability to work on multiple tasks at once. Self-motivated, analytical, and organized with a strong work ethic. Ability to prioritize competing demands and manage time effectively 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 Skylar 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, Brandon, to assess your technical skills for the role. Complete a Project Exercise This role requires strong communication and analytical skills, so we’ll ask you to complete a short exercise. You can take your time and use the resources available. We’ll assess your problem-solving abilities, writing skills, empathy, demeanor, and organization skills. 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 including 12 week Paid Parental Leave Retirement savings plan with company match Equity participation opportunities Monthly stipends to support a healthy lifestyle and learning and development opportunities 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.