Gusto

Head of Sales and GTM Operations

Gusto

full-time

Posted on:

Location Type: Hybrid

Location: Denver • California • Colorado • United States

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Salary

💰 $240,000 - $270,000 per year

Job Level

Lead

About the role

  • 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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
AI/automation initiativesagent-based systemsCRM systemsSalesforceAI integrationsautomation workflowsdata warehousesGTM toolsAI/ML conceptsprogram management
Soft Skills
leadershipmentoringcommunicationanalytical skillsorganizational changecross-functional alignmentfostering cultures of experimentationinfluencing executive audiencesbuilding high-performing teamsmeasurable impact
Certifications
Bachelor's degreeMBAtechnical graduate degree