Head of Sales and GTM Operations

Join to apply for the Head of Sales and GTM Operations role at Sistas In Sales 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. Job Description About The Role: We’re looking for a Head of AI-Native 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. 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. 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 $201,200–$251,000 in San Francisco & New York, and $171,200–$214,000 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. #J-18808-Ljbffr