General Manager, AI-Native Insurance Agency

Role Overview

Five Bays needs a General Manager (GM) to run and scale the AI-native personal lines insurance agency. As GM, you'll hold full P&L authority for the agency, covering revenue, margin, headcount, and budget, and you'll oversee the agency's existing sales and operations staff.

Beyond managing the business side, you'll own how the agency actually runs day to day, from the automations that generate quotes and the data pipelines feeding them to the systems the team relies on every day.

This is a hands-on operating role, not a carrier-relations or figurehead position, and part of the job is building the metrics infrastructure that lets us run Five Bays like a technology company rather than a traditional agency.

Key Responsibilities

P&l and Team Leadership

• Own the Five Bays P&L, including revenue, margin, operating budget, and headcount, and report results against plan to the CEO.
• Manage the agency's existing sales and operations staff, setting targets, coaching performance, and holding the team accountable to hit them.
• Set the agency's growth plan, including new states, carriers, and product lines, and the operating plan required to execute it.
• Sales and Financial Performance
• Drive sales performance, including quote volume, bind rate, and conversion, to meet the agency's revenue and financial targets.
• Build and maintain KPI dashboards covering cycle time, loss ratio inputs, and referral conversion, and report them on a set cadence to the CEO.
• Reconcile agency financials and production metrics, flagging discrepancies before they reach leadership reporting.

Systems and Operations

• Audit and fix data quality issues across quoting automations, including incorrect field mappings and downstream errors that cause bad quotes or failed binds.
• Diagnose and resolve CRM workflow issues affecting sales operations, service, and reporting.
• Own carrier onboarding, identifying integration gaps, standardizing the intake process, and reducing time-to-live for new carrier appointments.
• Identify and automate manual, repetitive processes across the agency, including renewals, endorsements, document handling, and referral intake.
• Partner with Engineering and Product to prioritize and scope fixes to internal tools based on operational pain points, not just feature requests.

Service and Compliance

• Improve customer service quality and turnaround time by fixing the operational root causes behind service complaints, not by staffing around them.
• Ensure agency operations stay compliant with insurance regulations across all licensed states.

Qualifications

• 7+ years in business operations, sales operations, or general management at a high-growth company, including direct P&L ownership; insurance industry experience is a plus, not a requirement.
• Track record managing a sales and/or operations team against revenue and margin targets, including performance management of existing staff.
• Demonstrated track record diagnosing broken processes or systems and shipping fixes, not just identifying the problem.
• Strong bias to action: comfortable in an early-stage environment with ambiguous scope and incomplete systems.
• Comfortable working directly in data: experience with CRM platforms, quoting/automation tools, or insurance agency management systems strongly preferred.
• Experience building and owning KPI reporting and financial reconciliation processes from multiple source systems.
• Track record identifying and implementing process automation (tooling, scripting, or workflow platforms) to eliminate manual work.
• Excellent written communication; able to translate operational and technical findings into clear recommendations for executive leadership.

Location & Reporting

• Based in California, with hybrid/remote flexibility depending on location.
• Reports to the CEO.