About this role
Location: United States (Remote)
Type: Full-time
Reports to: CRO
About Five Sigma
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.
The Role
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.
What You’ll Do (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.
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)
Advantages
- 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)
What Success Looks Like (First 6–12 Months)
- Build a strong pipeline of qualified enterprise opportunities in US target accounts
- Close new logo deals
- Become fluent in Five Sigma’s dual offering: Claims Management Platform , Clive™ as an AI layer
- Develop repeatable enterprise sales plays and contribute to scaling the US GTM engine
Why Join Five Sigma
- Sell a category-defining product in a massive market (insurance)
- Strong ROI-driven value proposition and real operational impact
- High ownership, high growth environment with excellent career upside
- Competitive compensation: base + commission + equity
Other facts
About Five Sigma
Five Sigma offers AI and automation technology for claims handling. Clive™, the industry’s first Multi-Agent AI Claims Expert, working on top of any existing claims management system (CMS), and Five Sigma's AI-native Claims Management Platform.
For P&C carriers, MGAs, TPAs, and reinsurers, Five Sigma delivers tangible results through claims technology: cost savings, productivity boost, cycle time reduction, improved accuracy, and better policyholder service.
Clive™, our award-winning Multi-Agent AI Claims Expert, adds AI and automation to any existing system to automate routine tasks, dynamically plan claim handling, and advance the claim automatically according to the insurer’s operating procedure (SOP). Clive manages multiple AI agents that handle and automate different tasks and claim handling stages, including: intake, triage, liability assessment, coverage, communications, fraud detection, compliance, settlement, and more.
Our customers can deploy Clive AI quickly, one agent at a time, and expand as they go. Adjusters are freed to focus on complex decision-making and better customer service.
Five Sigma’s Claims Management Platform is an AI-native CMS, with Clive built-in. Our platform includes 360° claim visibility, an omnichannel communication hub, and easily configurable workflows — offering unmatched efficiency and cost savings.
What you'll do
- The Enterprise Sales Manager will own and drive the full sales cycle, from prospecting to closing deals with various insurance organizations. This role involves leading executive-level conversations and collaborating cross-functionally to win and expand accounts.
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