Gusto · 2 days ago
Head of Sales and GTM Operations
Denver, CO
Full-time
Hybrid
Director/Executive
$240K/yr - $270K/yr
10+ years expGusto is on a mission to grow the small business economy by providing essential services like payroll and HR. They are seeking an AI-focused Head of Sales and GTM Operations to lead the transformation of their revenue engine into an AI-first operating model, overseeing a team that enhances decision-making and automates processes across Sales, Marketing, and Partnerships.
Bookkeeping and PayrollEmployee BenefitsEnterprise SoftwareFinancial ServicesFinTechHuman ResourcesSaaSSoftware
Responsibilities
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
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
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
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
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
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
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
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
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
Qualification
Required
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
Annual variable cash bonus (up to 20%)
Company
Gusto
Gusto is an HR and payroll platform that simplifies complex tasks, empowering businesses to focus on what matters most.
1001-5000 employees
H1B Sponsorship
Gusto has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (49)
2024 (54)
2023 (19)
2022 (37)
2021 (24)
Funding
Current Stage
Late StageTotal Funding
$746.1MKey Investors
Friends & Family CapitalT. Rowe PriceAkkadian Ventures
2023-01-28Series Unknown
2022-05-12Series E· $55M
2021-08-10Series E· $175M
Leadership Team
Josh Reeves
Head of Gusto (CEO) and Co-Founder. Building Gusto for the Long Term.
Edward Kim
Co-founder and Head of Technology
Recent News
CoinDesk: Bitcoin, Ethereum, Crypto News and Price Data
2026-01-18
Small Business Trends
2026-01-12
General Catalyst
2025-12-30
Company data provided by crunchbase