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Description
About Five Sigma
Five Sigma builds modern claims software and AI-powered workflows for carriers, MGAs, TPAs, and claims organizations. We help customers run faster, smarter, more automated claims operations with clear implementation boundaries, credible technical guidance, and real operational impact.
Role Overview
We are hiring a highly technical, customer-facing Sales Engineer to help Five Sigma win complex enterprise opportunities with precision. This person will be the bridge between sales, product, delivery, professional services, and the customer. They will help prospects understand exactly what they are buying, help internal teams understand exactly what must be delivered, and reduce the ambiguity that creates slow deals, scope creep, and surprises after close.
This is our first dedicated Sales Engineer hire. In practice, this person will usually join once an opportunity enters active technical evaluation - typically after the initial discovery/demo and before sandbox, pilot, or statement-of-work design - and stay involved through contracting, handoff, and early kickoff. After kickoff, the role should remain involved on demand where scope, timeline, or technical ambiguity still needs to be resolved.
We are looking for a technical architect first, a solutions storyteller second, and someone with real claims-domain credibility. The right candidate can handle enterprise architecture and integration conversations while also understanding the day-to-day realities of claims organizations.
What You’ll Own
Partner with Account Executives and sales leadership on qualified opportunities to secure the technical win.
Lead deep 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 that match the buyer’s operating reality.
Own the technical portion of demos, including API and integration architecture, solution design, and deep implementation questions.
Lead technical responses to DDQs, security reviews, compliance requests, and architecture conversations.
Create, manage, and track gap analyses; distinguish product capability, configuration, professional services, roadmap, and true custom requests.
Translate business requirements into clear solution designs, implementation assumptions, scope boundaries, and phased deliverables.
Own statement-of-work creation end to end, including technical scope, assumptions, dependencies, reusable templates, and appendices. Partner with the Account Executive and the deal review process on commercial alignment.
Produce solution outlines and scope appendices that make downstream planning clearer, more predictable, and easier for delivery and customer success to execute against.
Coordinate, plan, build, and lead sandbox or pilot events when deeper validation is needed.
Configure what is configurable in the platform and handle light, well-bounded customization - for example workflow automation, reporting, and dashboard configuration - within clear boundaries. Deeper engineering work remains with product and engineering.
Serve as a strong voice of the customer by surfacing repeat objections, missing capabilities, implementation friction, and product feedback.
Organize, systematize, and continuously improve the technical sales asset base, including demo assets, reference architectures, videos, FAQs, templates, and response materials.
Exercise strong judgment about when to push, simplify, escalate, or say no.
What Success Looks Like
Prospects leave technical evaluation with a clear understanding of what Five Sigma will deliver, what is standard, what is services-led, and what comes later.
Sales cycles on technically complex opportunities become faster and more predictable.
Win rates improve on opportunities supported by the Sales Engineer.
Statements of work become clearer, sharper, and easier for customers and internal teams to approve.
Fewer scope and implementation surprises are discovered after close.
Delivery begins with better-planned handoffs, cleaner assumptions, and higher implementation predictability.
Product and delivery leaders spend less ad hoc time filling pre-sales gaps.
Technical feedback from the field is captured and turned into better assets, process, and product input.
Requirements
5+ years in solutions engineering, sales engineering, solutions architecture, technical consulting, or similarly 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 the operating model and metrics of claims organizations with credibility, including core concepts such as loss ratio, leakage, cycle time, and the operational levers used to improve them.
Experience supporting complex enterprise software evaluations with multiple stakeholders.
Proven ability to run 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; comfort working with APIs, data mappings, workflow logic, and technical troubleshooting. Experience with Python and/or JavaScript is strongly preferred.
Strong written documentation skills and the 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 Have
Experience buying or implementing enterprise software from the customer side.
Experience with AI, LLM, 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.
Backgrounds That Tend to Fit
Candidates who tend to fit this role often come from one of the following paths:
Claims operations, claims transformation, or claims strategy roles inside a carrier, MGA, or TPA.
Claims consulting, system implementation, or transformation work done directly with claims organizations.
Solutions engineering, solutions architecture, or technical consulting roles at a claims technology, insurtech, or enterprise software company serving claims teams.
Why This Role Matters
Five Sigma is at the stage where founder-led and leader-led technical selling needs to become a repeatable function. This role exists to bring precision, credibility, and predictability to complex enterprise deals. It will help us sell the right work, scope it correctly, hand it off cleanly, and build a more scalable commercial motion without creating downstream chaos.
How We’ll Measure Success
Win rate and cycle time on Sales Engineer-supported opportunities.
Quality and speed of technical discovery, sandbox or proof-of-value execution, and statement-of-work turnaround.
Reduction in scope ambiguity and surprises discovered after close.
Predictability and quality of handoff into implementation.
Reduced pre-sales dependency on product and delivery leaders.
Customer confidence in the technical evaluation process.
