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Monoline · 2 weeks ago

Director of Insurance Operations

United States

Full-time

Remote

Senior Level, Lead/Staff

10+ years exp

Monoline is redefining the standalone personal umbrella insurance market with cutting-edge technology and a focus on long-term profitability. The Director of Insurance Operations will lead critical programs and support operations, ensuring efficient service delivery and operational excellence while advocating for agency partners.

Financial ServicesInsuranceInsurTechPayments

Responsibilities

Own the strategic direction and execution of SimpleSwitch, ensuring the program scales efficiently as volume increases

Lead, mentor, and scale a high-performance team (starting with 4-5 direct reports), setting the strategic vision for service quality and operational excellence

Act as the primary advocate for the Agency Experience, ensuring that both our automated tools and our human support team deliver seamless, top-tier service

Own the end-to-end SimpleSwitch lifecycle, driving the strategy for onboarding, data intake, mapping, and policy issuance

Architect and optimize a scalable onboarding framework, continuously refining discovery, data requirements, and agency experience to support volume growth

Establish structured, high-level communication cadences with agency leadership, including kickoffs, milestone check-ins, and post-transfer business reviews

Proactively identify structural bottlenecks and drive cross-functional initiatives with Product, Engineering, Underwriting, and Finance to resolve root causes and improve system velocity

Define the operational KPI strategy, utilizing data to forecast capacity needs and drive continuous improvement in cycle time, accuracy, and agency satisfaction

Build and lead a best-in-class support organization, fostering a culture of empathy, autonomy, and 'Batteries Included' execution

Strategically hire, onboard, and scale a remote-first, globally distributed team of employees and contractors

Direct the strategy for AI-assisted workflows and intelligent automation, ensuring our tooling evolves to keep the team lean and efficient as we scale

Partner with Product and Engineering to design the next generation of support tooling and automation

Oversee the creation of scalable documentation, knowledge bases, and training materials

Monitor support metrics at a macro level to identify trends, training gaps, and opportunities for product improvement

Qualification

Insurance operations leadershipAIAutomationCross-functional leadershipPersonal Lines Insurance LicenseMulti-channel support operationsOperational acumenHighly organizedSelf-directedProject managementDetail-oriented

Required

10+ years of experience in insurance operations, project management, or related roles, with at least 3+ years in a leadership position

Proven track record of building, scaling, and retaining high-performing remote teams

Strategic Automation: Demonstrated ability to leverage AI and automation not just to complete tasks, but to fundamentally redesign processes for efficiency

Operational Acumen: Strong financial and operational mindset, with the ability to balance service quality with cost-efficiency and long-term profitability

Cross-Functional Leadership: Experience driving initiatives across Product, Engineering, Underwriting, and Finance

Tooling Expertise: Experience managing multi-channel support operations

Highly organized, detail-oriented, and self-directed with the ability to manage multiple strategic priorities in a fast-paced startup environment