Outdoorsy

• 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.

• 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.

• 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.

• 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.

About the Outdoorsy Group Founded in 2015, Outdoorsy Group pioneered access to the outdoors by building the world’s leading outdoor travel ecosystem. Millions of guests trust Outdoorsy to create lifelong family memories, while hosts rely on its products and innovations to grow their businesses and unlock life-changing sources of income. Outdoorsy Group’s portfolio includes Outdoorsy.com, the largest outdoor travel and hospitality marketplace; the Destination Network, a growing collection of campgrounds and glamping retreats set in some of the country’s most iconic landscapes; and Roamly, its proprietary insurtech platform powering Outdoorsy.com and enabling insurance infrastructure for global marketplaces. Together, Outdoorsy Group’s businesses are united by a long-term mission: to restore our relationship with the outdoors—and with one another. About Roamly Roamly is a leading provider of innovative, specialty insurance solutions purpose-built for the modern mobility and marketplace travel economy. As a Lloyd's Coverholder and AI-first insurance innovator, Roamly delivers a robust platform, deep carrier partnerships, and an expanding ecosystem that empowers consumers, professional fleet owners, and marketplaces to unlock new revenue streams while reducing risk. Our technology harnesses AI, advanced automation, and embedded distribution to power tailored coverages for recreational vehicles, carsharing, and other emerging mobility models—covering everything from underwriting and claims to compliance, data analytics, and real-time risk management. Learn more at www.roamly.com. Role Overview We are looking for a systems-oriented Technical Operations Manager to own the "engine room" of our insurance business. In this role, you will manage and integrate our core technology stack—bridging the gap between our proprietary Policy Management System (PMS), sales CRM, and support ticketing platforms. You will not just administer tools; you will architect workflows that allow our agents + customers to bind policies faster and service policyholders more efficiently. The primary goal for this role is to optimize our operational productivity, vendor expense, and operational efficiency with our existing toolings by optimizing configurations, workflows, and account setup. You will be the expert of the tools, keeping a pulse on vendor updates to evaluate how we can benefit from new features while serving as the go-to resource for our front-line teams. Core Responsibilities 1. PMS, CRM and Support Administration - Sales & Retention Supports: Act as the primary administrator for our proprietary Policy Management System (PMS), Close.io (CRM), and Zendesk (Support). Manage user provisioning, custom fields, pipelines, and ticketing views. - Agency Management System (EZLynx & Bolt): Maintain our agency management system (EZLynx) and quoting exchange (Bolt). Troubleshoot rater issues, outages, and data discrepancies between systems. - Workflow Design: Map out the "Agent Journey." Identify friction points in existing processes and build automations to eliminate manual tasks and increase individual agent productivity. - IVR & Telephony: Manage call routing rules and IVR trees within Close.io/Zendesk Talk to ensure calls reach the right licensed agents based on state or carrier appetite. 2. Data Integration & Performance Analytics - End-to-End Data Integrity: Partner with Engineering and Data Analytics to architect seamless data flows from Lead (Close.io) to Quote (Bolt/EZLynx) to Ticket (Zendesk), performing regular audits to ensure policy data (numbers, dates, premiums) remains synchronized across the PMS, CRM, and AMS. - KPI Strategy: Partner with Sales and Service leaders to develop, refine, and enhance reporting frameworks that track critical business KPIs. - Unified Efficiency Reporting: Collaborate with Data Analytics to build cross-platform dashboards tracking agent performance and lifecycle bottlenecks, specifically monitoring Speed to Lead (Close.io), First Response Time (Zendesk), and Quote Turnaround Time (PMS/Bolt). 3. Support & Training - Front-line Support: Serve as the go-to person for questions and support from our front-line staff. - User Enablement: Support user training and ongoing troubleshooting to ensure the team is utilizing our tech stack to its full potential. 4. Strategy & Efficiency Optimization - Operational Productivity & Vendor ROI: Optimize configurations, workflows, and account setups to maximize operational productivity and minimize vendor expense. - Vendor Expert: Act as the "eyes-and-ears" for new updates from our vendors. Proactively evaluate new features and updates to determine if they can benefit the business.

**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.