Enterprise Sales Manager – Insurance / AI Claims
About The Position
Five Sigma is transforming insurance claims management with an AI-native SaaS platform and Clive™, the industry’s first multi-agent AI claims expert. Our solution helps insurers streamline operations, automate routine tasks, shorten claim cycle times, and improve accuracy and customer experience. We’re looking for an experienced Enterprise Sales Manager to drive growth across the US market. You will own the full enterprise sales cycle — from initial discovery through close — selling into various insurance organizations, including navigating complex buying committees. This is a high-impact role in a fast-growing company, with a product that delivers measurable ROI and operational transformation for claims organizations.
Requirements
- Native English speaker – MUST
- 3+ years of quota-carrying Enterprise B2B SaaS sales experience
- Experience in selling SaaS and AI solutions
- Proven track record of closing complex enterprise deals with multiple stakeholders
- Strong executive presence: ability to build trust and credibility with senior leadership
- Experience negotiating contracts and navigating legal/procurement/security processes
- Excellent discovery and consultative selling skills
- Highly organized, self-managed, and proactive
- Bachelor’s degree in Business or a related field (or equivalent experience)
Nice To Haves
- Experience selling into Insurance (Claims, Operations, Underwriting, or InsurTech ecosystem)
- Experience selling AI, automation, workflow, or enterprise transformation solutions
- Familiarity with claims systems (Guidewire / Duck Creek / etc.) or claims workflows
- Project management skills (ability to run multi-threaded deal cycles)
Responsibilities
- Own and drive the full sales cycle (prospecting → discovery → demo → business case → security/legal → procurement → close).
- Build and manage a pipeline of small to enterprise opportunities across P&C carriers, MGAs, and Third Party Administrators (TPAs)..
- Consistently meet/exceed quarterly and annual quota (new business + expansion).
- Lead executive-level conversations and align multiple stakeholders: Claims leadership, Operations, IT/CIO, Finance, Procurement, and Legal.
- Clearly articulate Five Sigma’s value proposition through high-impact demos, proposals, and presentations.
- Build ROI-driven business cases and tailor solutions to customer workflows.
- Navigate and negotiate SaaS contracts, including security reviews and legal/compliance processes.
- Collaborate cross-functionally with Product, Marketing, IT and Customer Success to win and expand accounts.
- Maintain accurate forecasting and pipeline hygiene in CRM.
Benefits
- Competitive compensation: base + commission + equity
- High ownership, high growth environment with excellent career upside
- Strong ROI-driven value proposition and real operational impact
- Sell a category-defining product in a massive market (insurance)
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What This Job Offers
Job Type
Full-time
Career Level
Manager
