Hybrid Head of Sales and GTM Operations

at Gusto

• Job title: Head of Sales and GTM Operations
• Job type: Full Time
• Experience level: Lead
• Salary: $240,000 - $270,000 per year
• Degree requirement: Bachelor's Degree
• Location requirements: Hybrid, Denver, United States

About the role

• AI-focused Head of Sales and GTM Operations leading Gusto’s revenue transformation into AI-first model. Overseeing team to enhance sales, marketing, and partnerships through intelligent automation.

Responsibilities

• Define and execute Gusto's comprehensive AI-native GTM operations strategy
• Build, lead, and mentor a team of AI Agent Builders, automation engineers, and RevOps specialists
• Oversee the design and deployment of agentic systems and intelligent workflows that automate manual GTM processes
• Lead the technical architecture connecting Salesforce, GTM tools, data warehouses, and AI platforms into a unified, intelligent revenue system
• Maintain operational excellence in territory design, quota setting, pipeline management, forecasting, and compensation
• Partner with Sales, Marketing, Partnerships, Growth, Finance, Data, and Product teams to identify high-impact automation opportunities
• Champion AI adoption across GTM teams through training, enablement, and change management programs
• Build comprehensive frameworks to measure AI/automation ROI—tracking productivity gains, conversion lifts, time saved, cost efficiency, and revenue acceleration
• Stay at the forefront of AI/ML developments in revenue operations.

Requirements

• 10+ years of progressive experience in GTM Operations, Sales Operations, or Revenue Operations, with at least 5+ years in a leadership role building and scaling high-performing teams in high-growth SaaS environments
• 2-3 years of hands-on experience leading AI/automation initiatives, building agent-based systems, or transforming operations through intelligent automation
• Deep expertise in CRM systems (e.g., Salesforce) and revenue technology stacks, with demonstrated ability to architect AI integrations, automation workflows, and system integrations across data warehouses and GTM tools
• Strong understanding of AI/ML concepts, LLMs, agentic systems, and modern AI tooling—able to evaluate technical trade-offs, guide build-vs-buy decisions, and translate AI capabilities into business value
• Exceptional ability to build, mentor, and scale technical operations teams working at the intersection of AI, automation, and business systems—fostering cultures of experimentation and measurable impact
• Proven track record of driving organizational change and AI adoption across multiple stakeholder groups, with excellent communication skills to influence executive audiences
• Exceptional analytical skills with ability to define success metrics for AI initiatives, measure ROI (productivity gains, conversion lifts, cost efficiency), and use data to optimize investments
• Strong program management skills to balance multiple complex initiatives, drive cross-functional alignment, and deliver measurable progress in fast-paced environments
• Deep understanding of the entire revenue lifecycle and how AI can enhance each stage, from demand generation to customer retention
• Bachelor's degree in Business, Computer Science, Engineering, or related field (MBA or technical graduate degree is a plus); AI-native mindset that sees automation as the default and is passionate about making humans more effective through intelligent systems.

Benefits

• Health insurance
• 401(k) matching
• Flexible work hours
• Paid time off
• Remote work options
• Professional development opportunities