Head of Revenue Operations / GTM AI Architect
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 Head of Revenue Operations / GTM AI Architect to serve as a key leadership partner to the CRO 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 own the full revenue operations function, spanning sales, marketing, and customer success, and be the architect of a next-generation GTM system that supports exponential growth without the heavy human capital requirements of a traditional SaaS operating model. You are not inheriting a mature system to manage. You are assessing what exists, 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 revenue leadership on strategy, architecture, and execution. Shape the systems, data, and workflows that will determine how the company scales. Help prove internally the same transformation Outmarket promises to customers externally. Lead a high-leverage function with meaningful ownership, visibility, and impact. WHAT YOU’LL DO Partner with leadership to 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. Translate business strategy into operational systems, processes, and data infrastructure. Lead and develop a small, high-leverage team as the function scales. Design a modern revenue technology stack with clean data architecture, strong integrations, and scalable governance. Evaluate and recommend solutions across CRM, quoting and billing, marketing automation, customer success platforms, data enrichment, inbound orchestration, and workflow automation. Continuously identify opportunities to replace manual processes with AI-powered alternatives. Ensure accurate, reliable data flow across revenue systems. Build the infrastructure for pipeline management, activity tracking, forecasting, deal velocity, territory planning, routing, compensation design, and capacity planning. Design operational workflows supporting customer onboarding, adoption tracking, health scoring, and renewal management Build inbound funnel infrastructure including lead capture, enrichment, scoring, routing, and sales handoff WHAT WE’RE LOOKING FOR 10+ years of progressive experience in revenue operations, business operations, or go-to-market strategy at high-growth technology companies. 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 see sales, marketing, and customer success as a single interconnected revenue system and design accordingly. Strong cross-functional leadership and communication skills. Comfort working directly with founders in a fast-moving, resource-constrained environment. Active use of AI tools to improve personal productivity and identify areas where AI can replace manual work. 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.