Revenue Operations Lead / GTM AI Architect
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AI Summary
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 revenue growth does not need to scale linearly with people and the operating model can be 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 a Revenue Operations Lead / GTM AI Architect to serve as a key partner to our leadership and broader founding team. This role will own the revenue operations function across sales, marketing, and customer success, while designing the systems that allow Outmarket to scale efficiently.
You will be the architect of the full revenue operations function - spanning sales, marketing, and customer success - and you will be the architect of a next-generation GTM system that supports exponential growth.
You are not inheriting a mature system to manage. You are assessing what exists, applying what you've seen work in your past experience, defining what it should look like for an AI-native company at hyper-growth stage, and building it. You will bring analytical rigor, strategic thinking, and operational discipline to a founding team that is moving fast and needs a partner who can keep up.
WHY THIS ROLE
Build an AI-first revenue engine from the ground up with no legacy constraints.
Partner directly with founders and leadership on strategy, architecture, and execution.
Shape the systems, data, and workflows that will determine how the company scales.
Help drive internally the same transformation Outmarket promises to customers externally.
Lead a high-leverage function with meaningful ownership, visibility, and impact.
WHAT YOU’LL DO
Define the AI-first revenue architecture and go-to-market motion.
Own revenue metrics, target setting, forecasting, and performance management across the full GTM organization.
Work on defining our business strategy, then translate it into operational systems, processes, and data infrastructure.
Design a modern revenue technology stack with clean data architecture, strong integrations, and scalable governance. Ensure accurate, reliable data flow across revenue systems.
Evaluate, recommend, and implement solutions across CRM, marketing automation, customer success, data enrichment, inbound orchestration, and workflow automation.
Build the infrastructure for pipeline management, activity tracking, forecasting, deal velocity, territory planning, routing, compensation design, and capacity planning
WHAT WE’RE LOOKING FOR
4+ years of progressive experience in revenue operations or go-to-market strategy at high-growth technology companies (and 7+ years of total work experience)
Demonstrated experience owning systems, processes, and analytics across multiple GTM functions.
Strong analytical and strategic foundation, with the ability to move from board-level planning to execution.
Experience building infrastructure in early-stage or growth-stage environments, not just optimizing mature systems.
Deep understanding of the modern revenue technology landscape, and a clear perspective on how to create a single, interconnected revenue system
Strong cross-functional leadership and communication skills.
Comfort working directly with founders in a fast-moving, resource-constrained environment
BONUS IF YOU HAVE
Experience at a high-growth SaaS or AI company scaling from early traction to significant revenue.
Background in management consulting, investment banking, or strategic operating roles.
Experience launching or scaling a GTM motion in a new market or vertical.
Familiarity with emerging AI-native tooling across revenue systems.
Experience connecting billing, product usage, and revenue data into a unified operating model.
Exposure to vertical SaaS, insurtech, or financial services technology.
WHAT YOU’LL GET
Direct partnership with the founding team at a company defining a new category in commercial insurance.
The opportunity to build an AI-first revenue engine from the ground up.
Meaningful ownership over systems that directly shape company growth.
Competitive compensation and meaningful equity.
The ability to build and lead a high-impact function in a remote-first environment.
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