Obie

Role Description As a Client Manager at Obie, you are responsible for supporting Agency Account Managers in day-to-day activities, including but not limited to: - Recruiting and onboarding new agents - National appointments - Account management This position helps enable sales success by assisting account managers with: - Sales plans - Analyzing data - Identifying growth and engagement opportunities You will also play a crucial role in recruiting and onboarding support with new partners to help fuel Obie’s growth in the independent agent channel! Qualifications - 1+ years of experience working in an agency or with agency partners - Strong organizational skills with attention to detail - Ability to manage multiple priorities - Proactive problem-solving and ownership mentality - Knowledge of sales strategies, techniques, and best practices - Strong oral and written communication skills - Passion for early-stage startups and/or high growth environments - Able to deal well with ambiguity and maintain composure in complex situations - Proficiency in Microsoft Excel/Google Sheets, Power Point/Google Slides and CRM reporting tools - Commitment to continuous learning and professional development - Active Property and Casualty license required 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. - Next, you'll have a 45-minute video interview with the hiring manager, Aly Gromak, to assess your technical skills for the role. - This role requires strong planning, collaboration, and communication skills, so we’ll ask you to complete a short exercise to flex those muscles. - 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. Benefits - 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.

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 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.

Role Description The Senior QA Analyst is responsible for working with cross-functional subject matter experts to document, deploy and monitor business and application test cases. This position will require the crafting and deployment of testing strategies and the presenting of strategic findings to leadership to move the organization to action. Those successful in this role will be strategic thinkers with the ability to negotiate skillfully with stakeholders to find common ground and acceptable alternatives that satisfy the needs of multiple end users. Additionally, you will help drive overall strategy and prioritization of work efforts. What you'll Do - Collaborate with leaders and stakeholders across the company to understand the business, product and system requirements. - Thoroughly test software to ensure proper operation and freedom from defects utilizing knowledge of application architecture. - Maintain documentation of test results, assist in debugging and communicate to business stakeholders. - Utilize necessary analytical skills to develop and maintain knowledge of in-house/vendor systems, formulas, rate specifications, manual rules, and state filing information to identify unusual, inconsistent or error conditions. - Maintain a test repository and/or performance test results; identify and resolve problems in areas of test development/management; devise improvements to current procedures and develop models of possible future configurations. - Provide detailed, insightful, constructive, and actionable feedback based on testing outcomes; produce reporting and documentation for all testing efforts, results, activities, data, logging and tracking. - Create visibility and deepen collaboration during development to ensure more reliable releases. - Enhance tools, processes, and frameworks to bring insurance products to market. Qualifications - Bachelor’s degree or equivalent required. - 4+ years experience developing, executing and monitoring application and business test cases. - 4+ years experience in P&C insurance industry or insurtech preferred. - 2+ years experience creating test automation suites on web services preferred. - Proven expertise in reviewing/designing test cases, test strategies, and test plans for multiple application releases based upon decomposed technical and user requirements. - Strong experience and comfort within Salesforce, a Policy Administration System (PAS), GSuite and JIRA (or similar task management software). - Experience using Java and Python, and tools such as Postman, Percy, and Playwrite. - Experience with accessibility testing, cross browser/platform testing, performance and security testing. - Strong analytical techniques and technical communication skills with ability to communicate ideas clearly, concisely and effectively. - Proven experience working in cross-functional teams and communicating with colleagues in both business and technical roles. - Positive “can do” attitude and a desire to contribute to a growing, energetic working team; experience working within a fast paced agile software development environment. - High level of detail orientation, with the ability to prioritize competing demands and manage time effectively. - Ability to adjust and change direction with ease. - Ability to build trust and rapport cross functionally in a remote, dispersed environment. 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. 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. Next, you'll have a 45-minute video interview with the hiring manager, Denise Pickering, to assess your technical skills for the role. This role requires strong planning and analytical skills as well as collaboration and communication skills, so we'll also present you with a short exercise to complete to provide you a chance to flex those muscles. You will be able to complete this exercise on your own time, so please be thorough and use the resources available to you. We'll be looking to see your problem solving abilities, writing and communication skills, empathy, general demeanor, and ability to leverage key QA strategies. More on this when you get there! 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. Benefits - 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. $90,000 - $130,000 USD per year. During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.

Brief Summary of Role As the Director, Technical Project Management, you will lead and develop a growing team of TPMs while also staying deeply embedded in the work itself. This is a leadership role, but not a purely managerial one. We believe the strongest leaders in this function are people who can coach, guide, and raise the bar for the team because they themselves are highly capable practitioners of the work. In this role, you will set the vision, operating standards, and day-to-day effectiveness of the TPM function at Obie. You will lead the TPM team, own and evolve the TPM operating model, and directly support some of Obie’s most important XFN initiatives. You will help drive quarterly planning, resource alignment, execution visibility, spring and engineering Pod operations, and delivery maturity across Product and Engineering. You will serve as a stabilizing force across teams by bringing structure to ambiguity, clarity to planning, and accountability to execution. This role is ideal for a leader who is equally comfortable managing people, improving systems and process, and stepping in directly to run a complex initiative, facilitate alignment, or solve an execution problem when needed. The expectation is not just that you can lead TPM work, but that you understand it deeply enough to do it yourself when the moment calls for it. What you'll Do - Lead, coach, and develop Obie’s team of Technical Project Managers, creating strong standards around execution, communication, accountability, and team growth. - Lead Obie’s TPM function as a true player-coach - setting the vision and operating model for the team while staying close enough to the work to directly step into complex or high-priority initiatives when needed. - Own and continuously improve how Product and Engineering plan and execute work, including quarterly planning, roadmap visibility, resource planning, implementation planning, Pod support, sprint/process rhythms, and XFN delivery coordination. - Drive XFN planning and execution across major initiatives, partnering closely with Product, Engineering, Design, QA, PMO, and business stakeholders to maintain alignment, remove blockers, and ensure successful delivery. - Partner closely with the VP of Product on executive and leadership-level strategic initiatives, helping translate high-level priorities into clear plans, strong execution, and operational follow-through across the organization. - Manage scope, dependencies, and execution risk proactively, surfacing tradeoffs early and helping leadership make sound prioritization decisions without losing momentum. - Build and mature the systems, tooling, and processes that support delivery excellence, including Jira workflows, automations, reporting structures, knowledge sharing, and broader TPM operational practices. - Partner with Product, Engineering, and executive leadership to shape prioritization, planning, and execution decisions across the organization, ensuring the TPM function is helping drive the highest-impact work. - Act as a trusted partner to senior leadership by creating confidence in execution, improving operational maturity, and bringing calm, thoughtful leadership to complex work across the organization. What you'll Bring - Significant experience in Technical Project Management, Program Management, Engineering Program Management, or a similar delivery leadership role within a software or product organization. - Prior people leadership experience, including direct management, coaching, performance feedback, and team development, with a clear ability to raise standards and grow strong operators. - A strong belief in hands-on leadership - you are comfortable leading the TPM function while also staying close enough to the work to step in directly when needed. - Proven success driving complex, XFN initiatives from planning through execution and release in environments with multiple teams, shifting priorities, and high ambiguity. - Strong command of delivery operations, including quarterly planning, roadmap execution, resource planning, dependency management, risk management, milestone planning, and launch readiness. - Strong technical fluency and the ability to work effectively with engineers on implementation tradeoffs, technical dependencies, systems constraints, APIs, testing, and release sequencing. - Experience partnering effectively with senior product, engineering, and executive leaders on strategic initiatives, organizational planning, and cross-functional execution. - Excellent communication, judgment, and executive presence, with the ability to influence across senior leadership, build trust across functions, and create clarity in complex situations. - Experience improving operating systems and team processes over time, including strong working knowledge of Jira / Atlassian tools as meaningful levers for planning, visibility, and execution. - The ability to balance strategic leadership with tactical depth - zooming out to shape the function and zooming in when details matter. When applying, be sure to include your favorite emoji so we know that you’re a real human, who also loves emojis! 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 get to have a 45 minute video interview with the hiring manager, Adam Tsouras, to assess your technical skills. - Complete a Project Exercise This role requires exceptional leadership, planning, collaboration, and communication skills, so we’ll also present you with a short exercise designed to reflect the real work of a Director-level TPM leader at Obie. The exercise will give you an opportunity to demonstrate how you approach team leadership, XFN delivery, prioritization, operational process, and stakeholder communication in a fast moving environment. Because this is a senior leadership role, we’ll be looking not only at how you would execute the work yourself, but also how you would guide a team, create clarity, drive alignment, and build confidence across the organization. You’ll complete the exercise on your own time, so please be thoughtful and thorough in your response. We’ll be evaluating your problem-solving abilities, written communication, judgment, empathy, leadership presence, and your ability to bring structure to ambiguity while balancing strategic thinking with practical execution. More on this when you get there. - 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.

Brief Summary of Role Obie is looking for an innovative, bright and hard-working individual to join our underwriting team to help us accomplish our mission of combining insurance know-how and innovative technology to bring bottom line success for the programs in which we manage. Those successful in this role will have property underwriting experience within P&C insurance. 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 - Facilitate underwriting processes to maintain the profitability and integrity of the book of business - Ensure your assigned territory is performing profitably by monitoring relevant KPI’s; reacting to indicators where necessary and propose solutions as needed - Use your in-depth knowledge to find procedural efficiencies to continually evolve our best practices - Collaborate with TPAs to help manage & monitor post loss activity - Maintain the existing culture predicated on motivation and positive reinforcement while upholding a standard of accountability to self, team and company What you'll Bring - 2+ years of experience in P&C property underwriting - Detail orientation in everything you do: there is a lot of customer and policy information flying by you – having a keen eye here is essential - Strong analytical skills in assessing P&L within a book of business - Property inspection underwriting experience - Experience and comfort using a variety of tools from Excel and G-Suite to policy management systems - Excellent verbal and written communication skills to problem solve, answer questions, and leave a positive impression - Fearlessness and adaptability in a fast-moving, ever changing environment and ability to work on multiple tasks at once - 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, Joel Place, to assess your technical skills for the role. - Complete a Project Exercise This role requires strong underwriting, collaboration, 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, written skills, empathy, demeanor, and how well you apply underwriting 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. This will be a 60-minute video interview. 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 salary range for this role below. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc. The pay range for this role is: $60,000 - $80,000 USD per year (US) During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.

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 - Assist in overseeing Virtual Assistants from assignment creation to reviewing work 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! This conversation will be a 60-minute video interview. 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. $56,250 - $90,000 USD per year During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.

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 Technical Project Manager (TPM), you’ll drive end-to-end delivery for some of Obie’s most important product and platform initiatives - with a particular emphasis on supporting our insurance product work as it expands (new lines of business, partner/business requests, and delivery across multiple engineering pods). You’ll bring structure to ambiguity, translate goals into clear execution plans, and keep teams aligned as we ship in a fast-moving environment. You’ll coordinate scope, dependencies, risks, and release readiness while maintaining a high bar for quality - and you’ll be especially strong at protecting teams from scope creep by helping stakeholders make clear tradeoffs. What you'll do You speak fluent project management: You’ll manage objectives, scope, timelines with stakeholders across both business pillars and engineering pods. You’ll spot risks early and keep everyone in the loop on progress made and aligned on the path forward. Scope and tradeoffs are your superpower: Proactively manage scope creep, clarify decisions, and help stakeholders make tradeoffs so teams can execute predictably. You can herd cats while juggling flaming torches: You’ll track and report progress from kickoff to delivery, aligning project milestones with company goals all while coordinating with engineers, technical specialists, and PMs. You bring order to the sprint shaped chaos: You’ll facilitate sprint planning and ceremonies for an engineering pod, ensuring accountability, clarity, and momentum toward quarterly goals. Quality is your bar: Partner with QA/Engineering/Product to define acceptance criteria, coordinate test planning, facilitate QA/business readiness reviews, and ensure release confidence (without being the primary “test case writer” or PR reviewer) . You see both the forest and the tech stack: You’ll work closely with engineering to understand high level constraints and opportunities, making sure solutions are scalable, practical, and aligned with our architecture goals. You’re the glue that holds the pod together: You’ll build strong lines of communication with stakeholders and maintain transparency on goals while operating independently to get the job done. You can work async: You will be able to work independently and make decisions with minimal supervision. You also will be able to demonstrate your excellent communication skills, including the ability to build relationships internally and externally. What you'll bring 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, Regan Smith , to assess your technical skills for the role. Complete a Project Exercise This role requires strong planning, collaboration, and communication skills, so we'll also present you with a short exercise to complete to provide you a chance to flex those muscles. You will be able to complete this exercise on your own time, so please be thorough and use the resources available to you. We'll be looking to see your problem solving abilities, writing and communication skills, empathy, general demeanor, and ability to leverage key product management strategies. More on this when you get there! 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.