Outdoorsy

Account Executive

• Engage customers using a consultative sales approach to understand their insurance needs and recommend personalized solutions across property, casualty, and personal lines.
• Proactively identify opportunities for cross-selling and up-selling, and assist customers in transitioning between Roamly and third-party insurance carriers when appropriate.
• Clearly explain coverage options, policy terms, and insurance processes in a way that’s easy for customers to understand.
• Drive lead conversion through high-volume outbound outreach and responsive handling of inbound inquiries.
• Manage the complete sales process—from quoting insurance products using Roamly’s proprietary tools, to gathering underwriting information, and guiding customers through to policy purchase and binding.
• Maintain accurate and timely documentation of customer interactions and follow-ups using Close.AI.
• Stay current on all available insurance products, systems, and carrier platforms to deliver informed, high-quality service and support.

Insurance Account Executive

Claims Specialist

• Claims Management: Investigate, evaluate, and negotiate damage claims to reach fair and equitable settlements for all involved parties.
• Policy Interpretation: Interpret policy contracts to identify how coverage applies to particular losses and guide customers through the resolution process.
• Operational Excellence: Accurately document all key claims activities and process/index all claims-related documents.
• Asset Recovery Support: Assist the department with total loss vehicles, including monitoring salvage, obtaining forms, and processing payments.
• Innovation: Proactively assess the current state of processes and practices to drive recommendations for improvement.
• Team & Collaboration: Partner with external partners to ensure customers receive high-level, efficient, and effective service.

Claims Representative

Data Scientist

• Develop Lead Scoring algorithms that predict the LTV of qualified insurance leads, and pass it back to our ad partners to optimize bidding strategies, as well as to our internal Sales team to prioritize outreach.
• Develop models to predict churn and claims losses across our insurance products. Work closely with the Underwriting team to ensure these models are integrated into business processes.
• Assist in the development of a dynamic pricing model to help RV marketplace hosts adjust prices seamlessly in response to seasonal and vehicle-based factors, as well as surges in demand.
• Develop models to predict what ancillary products should be recommended for upsell to a given Outdoorsy / Roamly customer.
• Use advanced statistical methods to conduct audience clustering and segmentation on both RV Rental and Insurance customers, and evangelize these findings across stakeholders in Marketing and Product.
• Collaborate closely with Data Analysts and Engineers to ensure that data pipelines and models are accurate and optimized.

Senior Data Scientist

Data Engineer

• Enhance Identity Resolution such that there is a source-of-truth Customer 360 view that links users across our RV marketplace, internal insurance products, and 3rd-party insurance partners.
• Develop fuzzy matching algorithms to triangulate single users across data that lacks common IDs.
• Build and maintain scalable ELT/ETL pipelines (using tools like dbt, Airflow, FiveTran) that sync siloed SQL databases, external CRM data, and 3rd-party insurance and claims data into a unified warehouse (Redshift/BigQuery).
• Architect real-time data flows to feed an AI agent, achieving AI Readiness. Through Knowledge Graphs, Vector Databases, and Retrieval-Automated Generation, ensure agents can access e.g. latest policy status, upsell propensity scores, and customer history in near real-time.
• Own all aspects of data governance between our operational systems and the AI agent to ensure privacy, security and high-fidelity responses.

Technical Program Manager

• Manage and integrate our core technology stack—bridging the gap between proprietary Policy Management System, sales CRM, and support ticketing platforms.
• Optimize operational productivity, vendor expense, and operational efficiency with existing toolings by optimizing configurations, workflows, and account setup.
• Act as the primary administrator for Policy Management System, Close.io (CRM), and Zendesk (Support).
• Maintain our agency management system (EZLynx) and quoting exchange (Bolt).
• Identify friction points in existing processes and build automations to eliminate manual tasks and increase individual agent productivity.
• Partner with Engineering and Data Analytics to architect seamless data flows and ensure data integrity.

Technical Operations Manager

Chief Marketing Officer

• Demand Creation and Market Activation
• This is a high-impact, 6-month contract position with the potential to convert to a full-time Director role.
• The objective is to optimize our brand presence, cultural relevance, and awareness ahead of the peak summer season.
• The Director will drive marketing activity, help direct an earned PR strategy to establish high-impact demand that integrates directly with mid-to-lower funnel conversion activities.
• This role reports directly to the VP of Brand Marketing and is hands-on.
• The Director must be prepared to utilize emerging channels, strategic partnerships, and focused content marketing techniques.
• Key Cross-Functional & Management Relationships
• Reporting To: VP of Brand Marketing
• Key Internal Partners: Content Strategy, Creative, Performance Marketing, and Product Teams
• External Partners: PR Agency (management and budget oversight)

Director of Marketing and PR – Contract-to-Hire

Product Manager

• **Key Responsibilities & Deliverables**
• - **Product Execution & High-Velocity Delivery:**
• - **Drive the product development lifecycle** from requirement definition through launch and post-production iteration.
• - **Write clear and complete PRDs and user stories** to effectively translate business objectives into development priorities.
• - **Own the Roamly backlog**, collaborating daily with Engineering (ENG) and Design to maintain progress and ensure quality delivery.
• - **Support product quality** by conducting QA/UAT testing, managing defect resolution, and troubleshooting system issues with ENG to develop creative workarounds.
• - **Execute high-velocity iterations** by applying a "test and learn" approach to enhance existing features and distribution strategies.
• - **Support change management and rollouts**, including writing release notes and conducting user training for Sales and Service teams.
• **Operational Scope:**
• - **Support the Head of Product** in developing the knowledge base and Standard Operating Procedures (SOPs) for our **AI Agents and virtual assistants.**
• - **Optimize the Quote-to-Bind experience** across several distribution channels: **Digital, AI Agent, Embedded, Captive Agency, and Independent Agents.**
• - **Enhance the Customer Portal **to improve self-service capabilities and overall policyholder satisfaction.
• - **Drive operational efficiency for a growing customer base** by identifying pain points and supporting system workflows across the **Policy Management System (PMS), Close.io, and Zendesk** in partnership with Sales, Service, and Claims.
• - **Autonomously manage external partners and vendors**, facilitating technical integrations and ensuring successful, long-term partnerships with minimal oversight.
• - **Support Product Marketing** by creating product fact sheets, personas, and value propositions for new and existing products.
• - **Collaborate with Legal to ensure all products and features remain compliant with state insurance regulations.
• - **Leverage AI tools (e.g., Gemini, Claude) **for day-to-day productivity, rapid prototyping, market research, and analyzing customer feedback to identify business opportunities and inform prioritization.

Senior Product Manager

Insurance

• Take customer calls and handle email correspondence regarding billing questions, online payments, renewals, and cancellations.
• Process incoming policy change requests from customers.
• Review policy coverages and issue certificates of insurance, evidence of insurance, or binders.
• Retain customers by overcoming objections to cancellation and providing effective solutions.
• Upsell ancillary products such as roadside assistance, tire & wheel protection, and pet insurance.
• Identify opportunities to cross-sell and transfer new business leads to the sales team.

Insurance Account Executive

Claims Representative

Senior Data Scientist

Data Engineer

Technical Operations Manager

Director of Marketing and PR – Contract-to-Hire

Senior Product Manager

Insurance Service Agent

Insurance Account Executive