Sales Engineer

Five Sigma•Rocky Hill, CT

About The Position

Five Sigma is hiring its first dedicated Sales Engineer to support complex enterprise opportunities for its claims software and AI-powered workflows. The role bridges sales, product, delivery, professional services, and customers, helping prospects understand what the company will deliver while ensuring internal teams have clear requirements and implementation boundaries. The Sales Engineer typically joins during active technical evaluation, after initial discovery and demonstration and before sandbox, pilot, or statement-of-work design. The role remains involved through contracting, handoff, and early kickoff, with on-demand involvement after kickoff when technical scope, timeline, or other ambiguity needs resolution. The position calls for a technical architect with strong customer-facing communication skills and credible claims-domain knowledge. The successful candidate will lead technical discovery and validation, develop tailored demonstrations and solution designs, guide architecture and integration discussions, respond to security and compliance reviews, manage gap analyses, and define implementation scope and assumptions. They will own statement-of-work creation in partnership with sales, coordinate sandbox or pilot events, configure platform capabilities within clear limits, and relay customer feedback to product and delivery teams. They will also build and improve the technical sales asset base and help establish a repeatable technical-selling function. Success means clearer technical evaluations and statements of work, faster and more predictable sales cycles, improved win rates, fewer post-close scope surprises, better implementation handoffs, reduced ad hoc pre-sales demands on product and delivery leaders, and stronger customer confidence.

Requirements

At least 5 years in solutions engineering, sales engineering, solutions architecture, technical consulting, or a similar customer-facing technical role 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.
Ability to lead technical discovery and convert 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 inside 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 aligned with buyers’ operating realities.
Own the technical portions of demos, including API and integration architecture, solution design, and implementation questions.
Lead technical responses to DDQs, security reviews, compliance requests, and architecture discussions.
Create, manage, and track gap analyses, distinguishing product capability, 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 end to end, including technical scope, assumptions, dependencies, templates, and appendices; partner with the Account Executive and deal review process on commercial alignment.
Produce solution outlines and scope appendices that support clearer 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 handle light, well-bounded customization, such as workflow automation, reporting, and dashboard configuration; deeper engineering work remains with product and engineering.
Surface recurring 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 say no.
Improve technical-sales processes and assets so complex enterprise deals can be scoped and handed off predictably.