Head of Sales and GTM Operations

Gusto

🔍 Observed

$240K - $270K USD

Denver, CO;San Francisco, CA;New York, NY;United States - Remote First seen 3 weeks ago Last seen 3 hours, 45 minutes ago Greenhouse

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Job Description

AI Summary

• Lead Gusto's transformation into an AI-first sales and go-to-market operation by defining strategy, building AI agent infrastructure, and overseeing automation across sales, marketing, and partnerships. • Build and mentor a team of AI Agent Builders and operations leaders to design, deploy, and optimize intelligent workflows that replace manual processes and drive measurable revenue impact. • Partner with the CRO, Revenue Operations leadership, and cross-functional teams (Data, BizTech, GTM) to architect AI-powered solutions for sales productivity, marketing personalization, and customer intelligence. • Establish governance frameworks, evaluation standards, and best practices for deploying agentic systems at scale while managing technology selection, vendor partnerships, and build-vs-buy decisions. • Reports to Head of Revenue Operations at Gusto, a Denver/San Francisco/New York-based company supporting 400,000+ small businesses with payroll, HR, and benefits solutions.

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 developments in revenue operations. Evaluate emerging technologies (LLMs, AI agents, automation platforms) and determine how Gusto can leverage or build competitive advantages through AI-native operations.

Here’s what we're looking for:

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.

Compensation

Our annual base salary compensation range for this role is $240,000 - 270,000 in San Francisco & New York, and $204,445 - $230,000 in Denver & Atlanta. This role is also eligible for an annual variable cash bonus (up to 20%). Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

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Job Information

Company:
Gusto
Location:
Denver, CO;San Francisco, CA;New York, NY;United States - Remote
Work Location:
Remote
Experience Level:
Senior
Source:
Greenhouse
Status:
Active

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65 /100

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