Technical Operations Manager - Contract

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.

Requirements

Required Qualifications

• Experience: 4+ years in Technical Operations, RevOps, or Systems Administration, preferably in the Insurtech or Fintech space.
• Tech Stack Expertise:

• Preferred: Configuration experience with Zendesk (Triggers, Automations, Explore) and Close.io (Sales pipelines, Smart Views, Email Sequences).
• Preferred: Hands-on experience with EZLynx and/or Bolt (Rating engine, AMS, Retention Center).

• Technical Skills (Must Have): Ability to collaborate with Engineering on data architecture and integration workflows. Ability to read/troubleshoot JSON data logs is a strong plus.
• Industry Knowledge: Basic understanding of the insurance lifecycle (Marketing, Quoting, Binding, Endorsements, Renewals).

Benefits

$50 - $85 hourly rate, DOE