Head of Sales and GTM Operations

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy. 

About the Role:

We're looking for an AI-focused Head of Sales and GTM Operations to lead the transformation of Gusto's revenue engine into an AI-first operating model. This role will oversee a team of AI Agent Builders and operations leaders who are redefining how Sales, Marketing, and Partnerships work at scale—replacing manual processes with intelligent automation, enhancing decision-making with AI-powered insights, and building the infrastructure for autonomous revenue operations.

This is a rare opportunity to lead both the strategic vision and execution of AI transformation across GTM. You'll build and scale a high-performing team that designs, deploys, and optimizes AI agents and workflows that drive measurable revenue impact. Reporting into the Head of Revenue Operations, you'll partner directly with the CRO and executive leadership to architect the future of how Gusto sells, markets, and grows.

About the Team:

The Revenue Operations team is the connective tissue between strategy, systems, and execution across Gusto’s Go-to-Market (GTM) organization. We enable Sales, Marketing, and Partnerships to operate efficiently, make data-informed decisions, and deliver exceptional experiences to customers and partners.

As Gusto embraces an AI-first future, this team is building the infrastructure, workflows, and evaluation frameworks that power intelligent, high-performing GTM operations. You’ll collaborate closely with RevOps, Data, BizTech, and GTM leadership to bring automation and AI to life across our revenue systems and processes.

Here’s what you’ll do day-to-day:

• AI Strategy & Vision: Define and execute Gusto's comprehensive AI-native GTM operations strategy. Set the roadmap for AI adoption across sales productivity, marketing personalization, partner operations, and customer intelligence. Drive technology selection, vendor partnerships, and build-vs-buy decisions that balance innovation with scalability.
• Team Leadership: Build, lead, and mentor a team of AI Agent Builders, automation engineers, and RevOps specialists. Foster a culture of experimentation, rapid iteration, and measurable impact. Develop talent that can translate complex business problems into elegant AI-powered solutions.
• Agent & Automation Architecture: Oversee the design and deployment of agentic systems and intelligent workflows that automate manual GTM processes. Establish governance frameworks, evaluation standards (prompt reliability, latency, cost, business impact), and best practices for safe, scalable AI deployment across revenue teams.
• AI Infrastructure & Integration: Lead the technical architecture connecting Salesforce, GTM tools, data warehouses, and AI platforms into a unified, intelligent revenue system. Ensure data quality, system reliability, and seamless integration across the revenue tech stack.
• Revenue Operations Excellence: Maintain operational excellence in territory design, quota setting, pipeline management, forecasting, and compensation—while progressively embedding AI capabilities that enhance efficiency, accuracy, and strategic insight.
• Cross-Functional Leadership: Partner with Sales, Marketing, Partnerships, Growth, Finance, Data, and Product teams to identify high-impact automation opportunities. Drive alignment on trade-offs, prioritization, and resource allocation. Translate business needs into technical requirements and AI capabilities into business value.
• Change Management & Adoption: Champion AI adoption across GTM teams through training, enablement, and change management programs. Ensure every AI initiative ships with clear ownership, measurable outcomes, and user feedback loops.
• Performance & Impact Measurement: Build comprehensive frameworks to measure AI/automation ROI—tracking productivity gains, conversion lifts, time saved, cost efficiency, and revenue acceleration. Use data to continuously optimize and prioritize AI investments.
• Market Intelligence & Innovation: Stay at the forefront of AI/ML development