Enterprise Sales Manager, Insurance

About the Role As Enterprise Sales Manager, Insurance, you will build and lead a team of Account Directors focused on driving strategic growth across the world’s largest insurance carriers and financial protection organizations. You’ll be a hands-on front-line leader responsible for helping your team navigate complex enterprise sales cycles, deepen executive relationships, and drive adoption of OpenAI’s platform across highly regulated insurance environments. This role will shape how OpenAI partners with insurers as they rethink underwriting, claims operations, customer engagement, distribution, risk analysis, and employee productivity through AI. You will help define the GTM strategy, operating model, and industry playbook for one of OpenAI’s most strategic Financial Services verticals. Key Responsibilities Recruit, develop, and lead a high-performing team of Insurance Account Directors focused on large enterprise insurers across North America. Create a strong coaching culture with frequent deal reviews, account strategy sessions, ride-alongs, and structured 1:1s that elevate team performance. Define and refine the GTM strategy for insurance accounts, including account prioritization, executive engagement strategy, and territory planning. Drive disciplined pipeline generation, forecasting accuracy, and operational rigor across a complex enterprise sales motion. Guide teams through highly consultative, multi-stakeholder opportunities involving technology, security, compliance, legal, and procurement stakeholders. Help customers translate AI and API capabilities into measurable business outcomes across insurance use cases such as underwriting, claims operations, customer service, broker and agent enablement, risk assessment, workflow automation, and employee productivity. Lead teams selling into highly regulated environments with a deep understanding of insurance-specific compliance, governance, and data security considerations. Partner closely with Product, Solutions Architecture, Technical Success, Legal, Security, and Finance to help customers successfully deploy AI at enterprise scale. Provide structured feedback to Product and leadership teams on insurance customer requirements, competitive dynamics, industry trends, and feature gaps. Partner with Marketing on insurance-focused events, executive engagement strategies, and industry campaigns that generate qualified pipeline and deepen strategic relationships. Establish a culture of accountability, operational excellence, and customer obsession while maintaining a low-ego, highly collaborative team environment. What We’re Looking For 15+ years of enterprise sales, GTM, or sales leadership experience, with significant experience leading teams selling into large insurance organizations. Proven track record building and scaling enterprise sales teams responsible for complex, strategic accounts and large revenue targets. Deep understanding of the insurance landscape, including how carriers evaluate and adopt emerging technologies within regulated environments. Experience leading consultative, multi-product, or platform-based sales motions involving executive stakeholders and technical buyers. Strong operational rigor and comfort managing forecasting, pipeline health, territory planning, and performance management at scale. Ability to operate effectively in fast-moving, ambiguous environments while helping teams maintain focus and execution discipline. Strong executive presence with the ability to engage credibly with CIOs, CTOs, Chief Digital Officers, Claims and Operations leaders, Data & AI leaders, and line-of-business executives. Low-ego, culture-first leader who builds trust quickly, develops talent, and creates high-performing teams. Public company experience strongly preferred. Skills & Experience Non-Negotiables Proven experience leading enterprise sales teams focused on large insurance or broader financial services customers. Strong understanding of regulated enterprise