Founding Sales Engineer
ABOUT OUTMARKET
Outmarket is an AI-powered platform purpose-built for commercial insurance agencies. We help agencies grow revenue and reduce E&O risk without adding headcount by amplifying what their best people do across every customer engagement and workflow.
We are in hyper-growth mode. Not the traditional SaaS kind, where you scale revenue by scaling people in lockstep. We are building for the AI era, where growth is not tied to adding people linearly and the operating model looks fundamentally different from traditional SaaS. Our customers are learning how to compete and win at a new scale using AI, and we are building that same model internally.
ABOUT THE ROLE
We are hiring our first Founding Sales Engineer to build the pre-sales technical motion from the ground up. There is no inherited playbook, no existing SE team, and no legacy process to manage. You will define how Outmarket demos, handles objections, runs proof-of-value engagements, and prepares for technical close.
Reporting directly to the CRO, you will both build the system and run it in real customer engagements. What you create will become the foundation for how the SE function scales over time.
WHY THIS ROLE
Build the SE function from zero with direct access to the CRO and broad visibility across the company.
Work with a product that genuinely impresses buyers and solves urgent, real-world problems.
Greenfield ownership to define the demo narrative, proof-of-value framework, objection handling, and hiring bar for the future team.
Play a central role in shaping how Outmarket wins in market as the company scales.
Receive meaningful equity at an early, high-growth stage.
WHAT YOU’LL DO
Design and document the end-to-end pre-sales motion, including demo structure, discovery framework, proof-of-value process, and technical objection handling.
Build a repeatable demo environment and a library of tailored use cases by agency size, line of business, and buyer persona.
Establish a tight feedback loop between pre-sales and product by capturing what wins, what stalls, and what buyers are asking for.
Define the future SE hiring profile, onboarding playbook, and performance benchmarks.
Partner with the CRO on SE KPIs, pipeline coverage standards, and capacity planning.
Own product demonstrations end to end and tailor each engagement to the buyer’s context.
Support a high-volume mid-market motion without sacrificing quality.
Translate product capabilities into tangible business outcomes such as revenue growth, producer efficiency, and E&O risk reduction.
Partner with AEs during discovery, objection handling, and technical close.
Build deep fluency in commercial insurance agency operations and where Outmarket fits into them.
WHAT WE’RE LOOKING FOR
5 to 10 years of experience in sales engineering, solutions consulting, or pre-sales in B2B SaaS.
Proven track record operating in a high-volume, high-quality pre-sales environment.
Experience building or significantly contributing to demo environments, playbooks, proof-of-value frameworks, or onboarding systems.
Strong product instincts and the ability to explain complex platforms clearly to non-technical buyers.
Excellent discovery, listening, and consultative selling skills.
Comfort working in an early-stage environment where you are building the process while running it.
Strong communication skills across operations, finance, and executive stakeholders.
BONUS IF YOU HAVE
Exposure to commercial insurance, insurtech, or financial services.
Experience selling workflow automation, document AI, or data extraction solutions.
Experience hiring, coaching, or developing SE talent as a function scaled.
Active use of AI tools to improve productivity, account research, and demo preparation.
WHAT YOU’LL GET
Competitive salary and performance-based compensation.
Meaningful equity reflecting the founding nature of the role.
Full health, dental, and vision benefits.
Remote-first flexibility, with periodic travel for team and customer engagements.
Direct access to the CRO and founding team from day one.
