Two Chicks With A Side Hustle

Remote – U.S. | Full-Time | Commercial Insurance Support

đź§ľ About the Role
At Pie Insurance, we’re baking up something better for small businesses—affordable, tech-driven commercial insurance. As an Underwriting Associate, you’ll be the connective tissue between underwriting, sales, and our agency partners. You’ll assess submissions, research risk, and keep the wheels turning on our smart, scalable platform. Your sharp eye and analytical chops will help shape a high-performing book of business while keeping our process “as easy as pie.”


âś… Position Highlights
• Full-Time | Remote (U.S.)
• $50,000–$60,000 base salary + equity
• Comprehensive health benefits, 401k match, generous PTO
• Mission-driven startup disrupting the insurance game with data


📋 What You’ll Own
• Analyze new business submissions and quote revisions
• Evaluate risk appetite for workers’ comp and P&C coverage
• Communicate with underwriters, sales reps, and agency partners
• Research exposure risk using tools like OSHA, SAFER, and other platforms
• Enter and maintain submission data in CRM and internal systems
• Request additional info to complete quotes or bind policies
• Stay current on underwriting best practices and guidelines


🎯 What You Bring
• High school diploma required; bachelor’s preferred
• 1+ year in commercial insurance preferred (workers’ comp ideal)
• Strong attention to detail and time management in high-volume settings
• Knowledge of online risk tools (OSHA, SAFER, etc.)
• Fluent with platforms like Salesforce, Excel, Google Suite; Slack/Teams a plus
• Clear written and verbal communication, especially in cross-team collaboration
• Tech-forward mindset—ready to improve legacy processes through smart systems
• Adaptable and curious, with a drive to improve every workflow


đź’ˇ Why Pie?
• Competitive compensation and stock options
• Tech-first approach to transforming a massive industry
• You’ll see your work have real impact, every day
• Values-led culture: we’re dreamers, builders, and people who give a damn


✍️ Apply Now
Help us make commercial insurance something small businesses can actually love. Apply today and bring your skills to a mission that matters.

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