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About the Role

Lead the closing team responsible for converting warm inbound inquiries and outbound pipelines into bound insurance policies. Directly manage and coach a high-volume team of licensed Insurance Account Executives (AEs). Scale closing ratios and ensure the team consistently crushes its monthly revenue targets.

Responsibilities

• Manage, mentor, and scale a high-volume team of licensed Insurance Account Executives (AEs) to meet and exceed monthly quotas.
• Conduct regular 1-on-1s, call shadowings, and script breakdowns.
• Train the team on consultative sales techniques, value-based selling, and advanced objection handling.
• 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.
• Work with SDR Manager and Marketing teams to calibrate lead quality, streamline high-velocity handoffs, and feedback loop data.
• Keep the team up to speed on current underwriting guidelines, multi-carrier platform updates, and compliance standards across different states.
• Drive a competitive, collaborative, and high-accountability environment where agents are excited to win together.

Requirements

• 3+ years of sales leadership experience, preferably managing inside sales or high-velocity closing teams within tech, insurtech, or a progressive brokerage environment.
• 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.
• Manage by numbers, not just feelings.
• Experienced with modern sales tools (CRM/dialers like Close.ai, Salesforce, or HubSpot).
• Ability to coach a team to explain complex coverage options, policy terms, and value props in simple, straight-talk language.
• Thrive in fast-paced, fluid environments where processes evolve quickly as the company scales.

Skills

• High-energy leadership
• Rigorous data tracking
• Fast-paced, transactional Property & Casualty (P&C) sales
• Consultative sales techniques
• Value-based selling
• Advanced objection handling
• Pipeline management
• Metric tracking
• Lead routing
• Cross-functional alignment
• Underwriting guidelines
• Multi-carrier platform updates
• Compliance standards
• Competitive environment
• Collaborative environment
• High-accountability environment
• Sales tools (CRM/dialers like Close.ai, Salesforce, or HubSpot)
• Startup agility

Location

• Austin, TX
• San Francisco, CA

Work Type

• Hybrid
• Full-time
• Office position

Experience Level

• 3+ years of sales leadership experience

Salary/Compensations

• $75,000 base salary
• $150,000 On-Target Earnings (OTE)
• Uncapped commission
• Regular SPIFFs

Benefits

• Full health and welfare benefits package
• 401(k) match
• Flexible Paid Time Off
• RV rental discounts

About the Company

• Roamly Insurance Group (Roamly), a wholly-owned subsidiary of Outdoorsy Holdings, Inc., is the first full-stack Insurtech for travel enthusiasts.
• Roamly is where the insurance industry and technology intersect to enhance the customer experience.
• A disruptor in the specialty insurance space, Roamly removes traditional technology and coverage barriers by providing innovative protection for underserved markets across recreation lines and global mobility markets.