Founding Sales Engineer
Outmarket AI · Remote (US) · Full-Time · Reports to CRO
About Outmarket AI
Outmarket AI is an AI platform purpose-built for commercial insurance agencies. We help agencies grow revenue and reduce E&O risk without adding headcount — amplifying what their best people do in every customer engagement, across every workflow, and at every level of the organization.
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 the growth curve is exponential and the operating model is fundamentally different. Our customers are commercial insurance agencies learning to compete and win at a new scale using AI. We are building that same model internally and proving it every day.
About the Role
This is a founding role. There is no SE team, no SE playbook, and no inherited process. You will be the first.
Reporting directly to the CRO, you will own the entire pre-sales technical motion — building it from zero while simultaneously running it at volume. You will define how Outmarket demos, handles objections, runs proof-of-value engagements, and prepares for technical close. What you build here becomes the foundation of how we scale the SE function as the company grows.
This is not a role for someone looking to execute someone else’s system. It is for someone who has lived inside a high-functioning SE motion, knows what great looks like, and is ready to build it from scratch in a fast-moving, early-stage environment.
Why This Role
• Direct line to the CRO — you will have the visibility, access, and authority to shape the SE function from day one
• A product that genuinely impresses buyers — your job is to set it up right, not to oversell it
• Greenfield ownership — you define the demo narrative, the proof-of-value framework, the objection playbook, and the hiring bar for the team you will eventually build
• Meaningful equity in a company at an early, high-growth inflection point
• Remote-first with periodic travel for team and customer engagements
What You’ll Do
Build the SE System
• Design and document the end-to-end pre-sales motion: demo structure, discovery framework, proof-of-value process, and technical objection handling
• Build a repeatable demo environment and library of tailored use cases organized by agency size, line of business, and buyer persona
• Establish the feedback loop between pre-sales and product — capturing what wins, what stalls, and what buyers are asking for that we don’t yet do
• Define the SE hiring profile, onboarding playbook, and performance benchmarks so the function is ready to scale when the time comes
• Partner with the CRO to develop SE KPIs, pipeline coverage standards, and capacity planning models
Run the Revenue Motion
• Own the product demonstration process end to end, tailoring each engagement to the agency’s size, lines of business, and operational context
• Support 20–30 active mid-market opportunities per quarter across a team of Account Executives, operating at high velocity without sacrificing quality
• Translate product capabilities into specific, tangible business outcomes for agency buyers: revenue growth, producer efficiency, and E&O risk reduction
• Partner with AEs during discovery to uncover pain, handle technical and operational objections, and drive opportunities from interest to commitment
• Develop deep fluency in commercial insurance agency operations — how agencies are structured, how producers work, and where Outmarket fits into their day
What We’re Looking For
We are looking for someone who has done this before at scale and is ready to own it from scratch. You have been a top-performing SE in a high-volume motion, you understand what a great pre-sales system looks like from the inside, and you are ready to build one. Beyond that:
• 5–10 years in a sales engineering, solutions consulting, or pre-sales role in B2B SaaS
• Proven track record of high-volume, high-quality pre-sales execution — you have carried large pipelines and delivered consistently across them
• Experience building or meaningfully contributing to SE systems: demo environments, playbooks, proof-of-value frameworks, or SE onboarding programs
• Deep product instincts — you learn complex platforms quickly and explain them clearly to non-technical buyers
• Strong discovery and listening skills — you connect prospect pain to product capability without relying on a scripted approach
• Comfortable operating without a net in an early-stage environment where you are building the process as you run it
• Clear, credible communicator across multiple buyer levels — operations, finance, and executive
Bonus If You Have
• Exposure to commercial insurance, insurtech, or financial services
• Experience selling workflow automation, document AI, or data extraction solutions
• A track record of hiring and developing SE talent as the function you helped build began to scale
• Active use of AI tools to accelerate personal productivity, account research, and demo preparation
What You’ll Get
• Competitive salary and performance-based compensation
• Meaningful equity reflecting the founding nature of this role
• Full health, dental, and vision benefits
• Remote-first with flexible hours
• Direct access to the CRO and founding team from day one
How to Apply
Send your resume or LinkedIn to careers@outmarket.ai with a short note on why you’re excited about this space. Tell us about a pre-sales system or process you built — what you created, what problem it solved, and how it performed.
- We move quickly on strong candidates.
