Full-Time
Head of Sales and GTM Operations
Posted on 1/21/2026
Gusto
1,001-5,000 employees
Payroll, benefits, HR platform for SMEs
Compensation Overview
$240k - $270k/yr
Remote in USA + 3 more
More locations: San Francisco, CA, USA | New York, NY, USA | Denver, CO, USA
Hybrid
Office presence required around 2-3 days per week for local hires.
 Growth & Marketing (1) |
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- 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.
- 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.
Gusto provides payroll, benefits, and HR services for small to mid-sized businesses through a cloud-based platform. It automates payroll processing, employee benefits enrollment (health insurance, retirement), and HR tasks in one place via a subscription model with tiered plans. By centralizing these functions, it helps businesses save time, stay compliant, and avoid maintaining a large in-house HR team. Its goal is to help SMEs run people operations more efficiently and support growth with easy-to-use, scalable software.
Company Size
1,001-5,000
Company Stage
Series E
Total Funding
$706.2M
Headquarters
San Francisco, California
Founded
2011
Simplify's Take
What believers are saying
- 500,000 customers create a large base for AI and compliance cross-sell.
- AI adoption among new founders strengthens demand for automated SMB operations.
- Karbon integration expands Gusto through accounting-firm payroll workflows and referrals.
What critics are saying
- Rippling and Deel can pressure Gusto with broader workflows and aggressive pricing.
- A payroll or tax automation error would damage trust and trigger customer churn.
- Reliance on state retirement mandates exposes revenue to legislative reversals and delays.
What makes Gusto unique
- Cofounder embeds Gusto context into AI actions, unlike blank-slate copilots.
- Gusto connects payroll, benefits, compliance, and HR in one SMB platform.
- Natural-language control spans SMS, Slack, and web, reducing payroll workflow friction.
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Your Connections
People at Gusto who can refer or advise you
Benefits
It’s a marathon, not a sprint: Employees celebrating 5 or 10 years at Gusto enjoy a month-long sabbatical to travel and relax after all their hard work.
Meals and conversations: Free meals, snacks, and drinks to keep us fueled, but more importantly: they bring people together and foster community.
Wellness for every body: We’re proud to offer inclusive health care such as hormone treatments, gender-affirming surgery, therapy, family planning, and more.
The time you need: Our flexible PTO policy means every employee is encouraged to take the time they need now to keep doing great work, long term.
Family-friendly benefits: Fertility treatments, primary and secondary parental leave, sleep coaching, house cleaning for new parents, and more.
Be well, be you: Get free, comprehensive medical, dental, and vision benefits, plus a monthly fitness stipend and mental health resources too.
Growth & Insights and Company News
6 month growth
↑ 3%1 year growth
↑ 0%2 year growth
↑ 0%Tech news: Intuit, Gusto both tout Claude integrations. Published April 10, 2026 12:48 PM Updated April 10, 2026 5:00 PM Intuit, Gusto both tout Claude integrations; Oracle premieres Fusion Agentic Applications; Suralink launches Financial Statement Tie Out solution; and other accounting tech news and updates. Intuit, Gusto both tout Claude integrations. ThongSam - stock.adobe.com announced the launch of the TurboTax connector on Claude, which brings TurboTax capabilities directly into Claude, including personalized and real-time tax estimates, instant refund projections, connection to a live Intuit tax expert, and a personalized tax document checklist with in-app document capture capabilities. The company also announced enhancements to its existing ChatGPT integration. Based on a few questions about their tax situation - whether they're a freelancer, a homeowner, a retiree or all three - users can now receive a personalized checklist of which forms to gather. They can also upload documents directly within the TurboTax app in ChatGPT and pick up right where they left off in TurboTax to continue filing. Payroll solutions company , which sports a , also announced an integration with Claude. With the integration, user can ask in plain English questions such as "What drove my payroll increase last pay period?" or "How much have we spent on overtime this quarter?" Claude will provide answers, drawing directly on the user's Gusto account, without ever leaving the tool they're already in. Gusto also announced a similar integration with Slack, with the same capabilities.
Gusto acquires Mosey to add compliance capabilities. * Gusto acquired compliance platform Mosey to embed small business compliance tools into its payroll and HR platform. * The purchase allows Gusto to integrate state and local business registration, filings, and ongoing compliance directly into its platform that serves 400,000 small businesses. * Mosey will help Gusto attract compliance-first customers while adding value via new upsell opportunities. Payroll, benefits, and HR management solutions company Gusto has acquired business compliance platform Mosey. Financial terms of the deal were not disclosed, but Gusto plans to leverage Mosey to help its customers manage their compliance obligations. Mosey was founded in 2021 to help small business owners avoid common compliance pitfalls such as hiring without the right legal setup, configuring payroll incorrectly, and missing tax deadlines. "I started Mosey because I'd made every compliance mistake myself, and then I watched thousands of other businesses make the same ones," said Mosey Founder Alex Kehayias. "The problem isn't that small business owners don't care about compliance, it's that they shouldn't have to become experts in it. Joining Gusto means we can bring that vision to the millions of small businesses that need it most." "Building a business is hard enough without compliance getting in the way," said Gusto Co-Founder and Chief Product Officer Tomer London. "With Mosey now part of Gusto, we can do what Gusto has always done: take complexity off the plate of small business owners so they can focus on what they actually started their business to do. This is a natural extension of our vision to be the platform that helps small businesses start, hire, and grow." Acquiring Mosey will allow Gusto to offer state and local registration, filings, renewal, and ongoing compliance management directly within its own platform. Once integrated, Gusto's 400,000+ small business clients will be able to hire, pay their teams, and manage their compliance obligations from a single place. Specifically, Gusto will add: * State and local business registrations * Entity management, ongoing filings and renewals * Resolving agency mail * Real-time surfacing of new compliance obligations as businesses grow or expand to new states Strategically, Gusto will be able to use Mosey's technologies to attract clients seeking compliance strategies, but not necessarily HR capabilities. Additionally, it will allow Gusto to cross-sell Mosey's compliance capabilities to its existing customer base. This is another case of "rebundling" fintech, in which fintech platforms are piling on more capabilities to their long-standing platforms in order to add value and create a broader, more encompassing ecosystem for clients. The deal comes eight months after Gusto acquired retirement specialist Guideline to offer 401(k) retirement plans through its platform. Gusto, originally known as ZenPayroll, was founded in 2011 and provides a cloud-based payroll, benefits, HR management, and business financial management solution. If the San Francisco-based company continues down its current path of expansion, it may eventually offer corporate credit cards and business banking tools.
Gusto has acquired Mosey, an AI-powered business compliance platform, to expand its services beyond payroll and HR. The acquisition will integrate state and local registration, filing and ongoing compliance management into Gusto's platform, serving its more than 400,000 small business customers. Small businesses face significant compliance challenges, with firms under 50 employees spending approximately $14,700 per employee annually on compliance costs—20% more than large enterprises. Each new hire in a different state can trigger multiple registration and filing requirements across various agencies. Mosey was founded by Alex Kehayias after experiencing compliance difficulties firsthand. The combined platform will offer state and local business registrations, entity management, and real-time compliance alerts as businesses grow. Gusto Business Compliance is expected to launch later this year.
Elevate named best consumer Payments Platform for second consecutive year. Mar 19, 2026, 10:15 ET FinTech Breakthrough recognizes Elevate's cloud-based, AI-enabled platform that transforms how healthcare benefits are delivered and scaled DENVER, March 19, 2026 /PRNewswire/ - Elevate, a modern consumer directed benefits administration platform, today announced that it has been selected as winner of the "Consumer Payments Platform of the Year," in the 10th annual FinTech Breakthrough Awards. This is the second consecutive year Elevate has received this honor from FinTech Breakthrough, an independent market intelligence organization that recognizes the top companies, technologies and products in the global FinTech market. "Being recognized by FinTech Breakthrough for the second year in a row is a powerful validation of our mission to modernize how healthcare benefits work for real people," said Brian Cosgray, co-founder and CEO of Elevate. "We built Elevate to eliminate challenges that have long defined consumer-directed benefits. This award reflects the impact our platform is having - helping partners scale faster, reduce operational burden and give workers immediate access to the healthcare dollars they depend on." Elevate is redefining how consumer-directed healthcare benefits are delivered, making it easier for U.S. workers to access and use their healthcare dollars when they need them most. The industry's first fully cloud-based, API-driven and AI-enabled consumer-directed benefits platform, Elevate replaces legacy infrastructure with real-time automation and modern consumer experiences. The platform supports instant claims processing, real-time reimbursements, automated claims submission, and a single secure payment card that works across multiple benefit plans, including chip security and contactless payments. By removing friction from every step of the benefits journey, Elevate helps benefits administrators - such as Gusto, Rippling, and Rocky Mountain Reserve - deliver faster access to funds and a simpler, more intuitive experience for members. The company's scalable platform drives efficiency, reducing exceptions and customer support volume, even as new clients are onboarded. The results are measurable, as Elevate customers have reported achieving 40% to 50% new business growth, while reducing cases per customer by more than 60%. The FinTech Breakthrough Awards is the premier awards program founded to recognize the FinTech innovators, leaders and visionaries from around the world in a range of categories, including Digital Banking, Personal Finance, Cryptocurrencies, Lending, Payments, Investments, RegTech, InsurTech and many more. Elevate is named alongside two of its partners, Gusto and Rippling, and an elite group of distinguished winners across the financial services industries, including MasterCard, Nerd Wallet, Intuit, Betterment, Capital One, and others. About Elevate Elevate is the first completely cloud-based, API-driven and AI-enabled consumer-directed benefits platform with a focus on configurability, embeddability and real-time automation. The all-in-one platform can manage all types of benefit accounts, from health savings accounts (HSAs) to complex health reimbursement arrangements (HRAs), and even commuter and lifestyle accounts. Elevate's team of industry experts recognized the need for modern technology in an outdated benefits administration industry, which led to the creation of Elevate in 2020. To learn more visit www.elevate.ai and follow Elevate on LinkedIn. SOURCE Elevate
Gusto has selected zerohash to power stablecoin payout capabilities across its global payments platform, currently in beta. The partnership enables contractors worldwide to receive earnings instantly in digital dollars through zerohash's regulated onchain settlement infrastructure. The integration addresses growing demand from distributed workforces, as 11% of small businesses employed international contractors in 2025. Traditional cross-border payments take three to seven days, whilst Gusto's new system using US Real-Time Payments and stablecoins can move funds globally in minutes. Gusto, which serves over 400,000 small business employers, will offer stablecoin payouts with real-time settlement and onchain traceability. The service supports both custodial and self-custodial wallets, providing faster transfers and improved cash flow flexibility for global teams.