Ai Insurance Jobs in Boston, MA (NOW HIRING)

AACI Group is building the first AI-native insurance holding company: agencies, carriers, and digital products run on proprietary AI agents and models we build ourselves, not on off-the-shelf tools bolted onto legacy workflows. Our thesis: climate change is shrinking carrier appetite in catastrophe-prone markets faster than legacy agencies can adapt. We’re closing that gap with AI-driven underwriting data, loss prevention, and product delivery built for the way insurance actually works today.

Five Bays Insurance Agency is the flagship: the first agency built from the ground up to run on AI, not retrofit with it. Licensed in 13 states, writing California homeowners against the CA FAIR Plan, and growing fast.

Five Bays needs a General Manager (GM) to run and scale the first insurance agency built AI-native from day one. 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 to hit those targets. 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.

• 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.

• Pull and reconcile agency financials and production metrics from Attio, EZLynx, and QuickBooks, flagging discrepancies before they reach leadership reporting.

• 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 (Attio) 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.

• 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 13 licensed states.

• 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: SQL proficiency required; experience with CRM platforms, quoting/automation tools, or insurance agency management systems (EZLynx or similar) 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.

• Based in California, with hybrid/remote flexibility depending on location.

• Reports to the CEO.

There is no playbook for running an AI-native insurance agency; we’re writing it. This role owns the P&L and the operating system for Five Bays: full authority over revenue, margin, team, and how the agency runs day to day. You’ll report directly to the CEO with real authority to run the first agency of its kind as a business, and the work you do here becomes the template for every AACI business that follows.