Enterprise Sales Manager, Insurance

Role Overview

• 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.

Requirements

• 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.

Benefits

• Medical, dental, and vision insurance for you and your family, with employer contributions to Health Savings Accounts
• Pre-tax accounts for Health FSA, Dependent Care FSA, and commuter expenses (parking and transit)
• 401(k) retirement plan with employer match
• Paid parental leave (up to 24 weeks for birth parents and 20 weeks for non-birthing parents), plus paid medical and caregiver leave (up to 8 weeks)
• Paid time off: flexible PTO for exempt employees and up to 15 days annually for non-exempt employees
• 13+ paid company holidays, and multiple paid coordinated company office closures throughout the year for focus and recharge, plus paid sick or safe time (1 hour per 30 hours worked, or more, as required by applicable state or local law)
• Mental health and wellness support
• Employer-paid basic life and disability coverage
• Annual learning and development stipend to fuel your professional growth
• Daily meals in our offices, and meal delivery credits as eligible
• Relocation support for eligible employees
• Additional taxable fringe benefits, such as charitable donation matching and wellness stipends, may also be provided.