Sales Engineer - Insurance Claims

Five Sigma•Rocky Hill, CT

19d

About The Position

Five Sigma is hiring its first dedicated Sales Engineer to support complex enterprise sales opportunities for its claims software and AI-powered workflows. The role is highly technical and customer-facing, bridging sales, product, delivery, professional services, and customers. The Sales Engineer typically joins during active technical evaluation—after initial discovery and demos, and before sandbox, pilot, or statement-of-work design—and remains involved through contracting, handoff, and early kickoff. After kickoff, the role may provide on-demand support to resolve scope, timeline, or technical ambiguity. The position focuses on providing credible technical guidance and claims-domain expertise, clarifying what customers are buying and what must be delivered, and reducing ambiguity that can slow deals or create post-sale surprises. The Sales Engineer will support technical wins, shape solution designs and implementation boundaries, lead technical validation, create clear statements of work, and improve the repeatability of Five Sigma’s technical sales process and assets.

Requirements

At least 5 years of experience in solutions engineering, sales engineering, solutions architecture, technical consulting, or similar customer-facing technical roles in enterprise software.
Strong fluency in claims operations and claims organizations, gained through direct operator experience or sustained work with carriers, MGAs, TPAs, claims consultancies, or claims technology.
Ability to discuss claims operating models and metrics credibly, including loss ratio, leakage, cycle time, and operational improvement levers.
Experience supporting complex enterprise software evaluations involving multiple stakeholders.
Proven ability to lead technical discovery and turn ambiguous needs into clear solution designs and scope boundaries.
Experience building and presenting tailored demos, sandbox environments, pilots, proofs of value, or other technical validation motions.
Strong architecture instincts across APIs, integrations, cloud environments, data flows, security and compliance, and enterprise systems.
Hands-on technical fluency and comfort working with APIs, data mappings, workflow logic, and technical troubleshooting.
Strong written documentation skills and ability to produce client-facing technical deliverables, statements of work, and scoped implementation assumptions.
Ability to work cross-functionally and earn trust with sales, product, delivery, and executive stakeholders.
High ownership and comfort building a function from the ground up.

Nice To Haves

Experience with Python and/or JavaScript.
Experience buying or implementing enterprise software from the customer side.
Experience with AI, LLMs, workflow automation, document processing, copilots, or agentic systems.
Experience with low-code workflow tools, reporting and dashboard configuration, or scoped implementation planning.
Experience building repeatable demo factories, technical asset libraries, or pre-sales playbooks.
Experience with Salesforce, HubSpot, or similar systems used to operationalize technical sales workflows.
Background in claims operations, claims transformation, or claims strategy at a carrier, MGA, or TPA.
Background in claims consulting, system implementation, or transformation work directly with claims organizations.
Background in solutions engineering, solutions architecture, or technical consulting at a claims technology, insurtech, or enterprise software company serving claims teams.

Responsibilities

Partner with Account Executives and sales leadership on qualified opportunities to secure the technical win.
Lead technical discovery across workflows, data, security, integrations, architecture, and implementation constraints.
Build and deliver tailored demos, technical walkthroughs, prototypes, sandbox events, and proof-of-value motions.
Own the technical portion of demos, including API and integration architecture, solution design, and implementation questions.
Lead technical responses to DDQs, security reviews, compliance requests, and architecture conversations.
Create, manage, and track gap analyses, distinguishing product capabilities, configuration, professional services, roadmap items, and custom requests.
Translate business requirements into solution designs, implementation assumptions, scope boundaries, and phased deliverables.
Own statement-of-work creation, including technical scope, assumptions, dependencies, reusable templates, and appendices.
Partner with the Account Executive and deal review process on commercial alignment.
Produce solution outlines and scope appendices that support predictable downstream planning and execution by delivery and customer success.
Coordinate, plan, build, and lead sandbox or pilot events when deeper validation is needed.
Configure platform features and perform light, well-bounded customization, such as workflow automation, reporting, and dashboard configuration; deeper engineering work remains with product and engineering.
Surface repeat objections, missing capabilities, implementation friction, and product feedback as a voice of the customer.
Organize, systematize, and continuously improve technical sales assets, including demos, reference architectures, videos, FAQs, templates, and response materials.
Use sound judgment about when to push, simplify, escalate, or decline a request.