Head of Revenue Operations / GTM AI Architect

Help Redefine Insurance with AI

Remote

GTM

About Outmarket AI

Outmarket AI is an AI platform purpose-built for commercial insurance agencies. We help agencies grow their 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.

The Head of Revenue Operations is a key leadership hire in that mission.

About the Role

You will serve as the core partner to the CRO, handling all matters related to the operations of the GTM function, creating leverage for the CRO to focus on leadership and growth.

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.

What makes this role distinct: the systems you build internally will directly reflect and validate the transformation Outmarket drives for its customers. You are not just running RevOps—you are helping prove that AI-first companies operate at a different level.

Key Responsibilities

Strategy and Leadership

Partner directly with the CEO and CRO to define the AI-first revenue architecture and GTM motion that supports hyper-growth
Own revenue metrics, target-setting, forecasting, and performance management across the full GTM org
Translate business strategy into operational systems, processes, and data infrastructure
Lead and develop a small, high-leverage team—including cross-functional contributors and contractors—as the function scales
Serve as a thought partner to senior leadership on go-to-market strategy, hiring strategy, capacity planning, and organizational design

GTM Architecture and Systems

Design a next-generation, AI-first GTM stack with clean data schema, proper integrations, and governance standards built to scale
Evaluate and recommend the right mix of established and emerging solutions across CRM, quoting and billing, data enrichment, marketing automation, inbound orchestration, customer success platforms, and workflow automation
Continuously assess the evolving AI tooling landscape and replace manual processes with AI-powered alternatives wherever practical
Ensure accurate data flow across revenue systems so pipeline, billing, and customer data are always complete and reliable

Sales Operations

Build pipeline management, activity tracking, forecast reporting, and deal velocity infrastructure that gives leadership real-time visibility
Design territory planning, quota-setting, sales compensation plans, routing, and capacity frameworks that scale with the sales team
Establish sales effectiveness and productivity metrics that drive continuous improvement

Marketing Operations

Build inbound funnel infrastructure including lead capture, enrichment, scoring, routing, and sales handoff
Implement marketing automation workflows that support demand generation, nurture programs, and campaign measurement
Establish attribution reporting that connects marketing investment directly to pipeline and revenue

Customer Success Operations

Design operational workflows supporting customer onboarding, adoption tracking, health scoring, and renewal management
Build the data connections that allow CS to proactively surface expansion opportunities and at-risk accounts
Close the loop between post-sale outcomes and the broader GTM system for complete revenue visibility

Required Qualifications

10+ years of progressive experience in revenue operations, business operations, or GTM strategy at high-growth technology companies
Demonstrated experience owning systems, processes, and analytics across multiple GTM functions—sales, marketing, and customer success
Strong analytical foundation—comfortable working with data, building models, and deriving insights that drive operational and strategic decisions
Proven track record of building GTM infrastructure from early stage, not just optimizing mature systems
Experience with annual planning, target-setting, forecasting, and performance management at a growth-stage company
Strong working knowledge of the modern GTM technology landscape across CRM, marketing automation, customer success platforms, data enrichment, billing systems, and workflow automation
Ability to evaluate vendor tradeoffs and own implementation from design through go-live
Strong cross-functional leadership and communication skills—able to influence and align across sales, marketing, CS, finance, and product
Comfortable working directly with founders in a fast-moving, resource-constrained environment
Actively uses AI tools to accelerate personal productivity and identifies where AI can replace manual work across the GTM org

Nice to Have

Experience at a high-growth SaaS or AI company scaling from early traction to significant revenue
Background in management consulting, investment banking, or strategy—with a transition into operational roles
Experience launching or scaling a GTM motion in a new market or vertical
Familiarity with emerging AI-native tooling across CRM, marketing automation, customer success, data enrichment, inbound orchestration, billing integration, and process automation
Experience connecting billing, product usage, and revenue data into a unified GTM system
Exposure to self-serve or product-led growth motions alongside traditional sales-led GTM
Experience designing GTM systems that support non-linear, AI-enabled growth models
Background in or exposure to vertical SaaS, insuretech, or financial services technology

Who You Are

You are a strategic operator—equally comfortable in a board-level planning conversation and in the data doing the work yourself
You see sales, marketing, and customer success as a single interconnected revenue system and design accordingly
You bring analytical rigor to every decision, but you know when to move fast and iterate rather than wait for perfect information
You have built teams, developed people, and created structure where none existed before
You are energized by building from scratch in environments where the playbook does not yet exist
You stay current on how AI is changing the way GTM teams operate and apply it practically, not theoretically
You take ownership of outcomes and operate with founder-level accountability

Why This Role

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 with no legacy constraints
Your work will directly inform the product and market narrative Outmarket brings to its customers
A front-row seat to hyper-growth in the AI era, with the autonomy to shape how it happens
Competitive compensation, meaningful equity, and the ability to build and lead a function

Location: Remote | Periodic travel expected for team and customer engagements