Roamly - Sales Manager, Insurtech

About Roamly

Roamly Insurance Group (Roamly) is a wholly-owned subsidiary of Outdoorsy Holdings, Inc., dedicated to being the first full-stack Insurtech for travel enthusiasts. Roamly bridges the gap between the insurance industry and technology to enhance customer experiences. For more information, visit roamly.com.

About The Role

As our Sales Manager, you will lead a high-volume team of licensed Insurance Account Executives (AEs) to convert warm inbound inquiries and outbound pipelines into bound insurance policies. Your mission is to scale closing ratios and ensure the team meets and exceeds monthly revenue targets.

Key Responsibilities

• Team Leadership & Performance: Manage, mentor, and scale a high-volume team of licensed Insurance Account Executives (AEs) to meet and exceed monthly quotas
• Deal Coaching & Conversion: Conduct regular 1-on-1s, call shadowings, and script breakdowns. Train the team on consultative sales techniques, value-based selling, and advanced objection handling
• Pipeline & Metric Management: Closely track day-to-day metrics (close rates, talk time, average policy value, speed-to-lead) to spot bottlenecks and ensure efficient lead routing and execution
• Cross-Functional Alignment: Work hand-in-hand with our SDR Manager and Marketing teams to calibrate lead quality, streamline high-velocity handoffs, and feedback loop data
• Compliance & Product Mastery: Keep the team up to speed on current underwriting guidelines, multi-carrier platform updates, and compliance standards across different states
• Culture Carrier: Drive a competitive, collaborative, and high-accountability environment where agents are excited to win together

Requirements

• Experience: 3+ years of sales leadership experience, preferably managing inside sales or high-velocity closing teams within tech, insurtech, or a progressive brokerage environment
• Insurance Foundation: Active Property & Casualty (P&C) or General Lines insurance license is highly preferred. Deep comfort navigating insurance underwriting, quoting, and binding workflows is a must
• Data-Driven Mindset: You manage by numbers, not just feelings. Experienced with modern sales tools (CRM/dialers like Close.ai, Salesforce, or HubSpot)
• Consultative Sales Mastery: You know how to coach a team to explain complex coverage options, policy terms, and value props in simple, straight-talk language—leaving out the dry insurance jargon
• Startup Agility: You thrive in fast-paced, fluid environments where processes evolve quickly as the company scales

Benefits

• Growth Opportunity: Join a company in its early stages and help build its foundation for success
• Competitive Compensation: Receive a competitive salary with uncapped commissions
• Equity: Opportunity to earn equity compensation
• Comprehensive Benefits: We offer a full health and welfare benefits package, a 401(k) match, and flexible Paid Time Off
• Fun Office Atmosphere: Lively office, stocked with endless snacks, regular Happy Hours, catered lunches, and team building events
• Work-Life Balance: Enjoy RV rental discounts and a company culture that values a healthy balance between work and adventure

Compensation & Schedule

Base Salary: The base salary for this position is $75,000, with an On-Target Earnings (OTE) of $150,000
Schedule: This is a full-time office position