GTM Insights & Operations

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. About the Role and the Team Gusto's GTM team drives revenue across Indirect and Direct Sales, Channel Partnerships, and Expansion Sales — and this role is the connective tissue that makes it all work. As a GTM I&O Lead, you'll own the operating infrastructure, planning rhythms, and cross-functional programs that keep GTM moving at speed. This isn't a traditional ops role. You'll be embedded in the strategy — identifying where growth is won or lost, building the programs that unlock it, and designing the systems (including AI-augmented ones) that scale our capacity. You'll work directly with GTM leaders, Finance, Marketing, RevOps, and Product to translate ambition into execution. You'll own a set of routes-to-market end to end, which means accountability for outcomes — not just coordination. This role blends strategic program management, operations, and business strategy. You will join Gusto's Insights & Operations (I&O) team, and collaborate with a community of I&O peers across the business. I&O partners are trusted operators who bring urgency, clarity, and execution discipline to Gusto's most important initiatives—driving both strategy and execution, not one or the other. Here’s what you’ll do day-to-day: • Own the operating rhythm for your routes to market—roadmaps, OKRs/targets, planning, and business reviews (e.g., weekly forecast reviews, QBRs, steercos). • Launch and manage cross-functional programs end to end, bringing urgency and clarity to initiatives that are ambiguous, at risk, or stalled. • Lead fiscal-year planning —translating strategy into concrete goals, owners, and timelines. • Own performance-lever workstreams: identify where growth is won or lost, structure the analysis, and drive cross-functional action. • Pilot AI-augmented approaches to program management and ops, and design re-usable automation patterns and AI agents that scale capacity across I&O and other Gusto teams. • Partner on Gusto-wide efforts and other high-impact cross-functional programs. We are looking for a rising business leader with: • 5+ years of experience in business operations, revenue/GTM operations, consulting, program management, or product management, ideally in high-growth technology companies. • Craft depth in one or more go-to-market disciplines. We're looking for meaningful experience across some of the following: sales, marketing, partnerships, or pricing & packaging as a craft—and if not those, deep experience in revenue analytics or finance as a craft. • Strong program management skills → end-to-end ownership of complex, cross-functional initiatives. • Operational excellence → proven ability to run team rituals and operating mechanics, including roadmaps, metrics/OKRs, forecasting, and business reviews. • Analytical rigor → comfortable working with data to surface insight, size opportunities, and inform senior decisions. • Excellent communication and collaboration skills → builds strong cross-functional relationships across sales, marketing, partnerships, product, finance, and operations. • Ownership mindset → proactive, comfortable flexing into ambiguous problems at any altitude. • Change leadership → able to guide teams through change with clear communication. • AI-Native Mindset → naturally seeks out ways to integrate AI into workflows to accelerate documentation, build smarter systems, and improve decisions. • Alignment with Gusto's values → customer empathy, grit, and a passion for helping small businesses thrive. Our cash compensation amount for this role is between $158,300 - $195,237/year in Denver and between $185,955 - $229,345/year for New York/San Francisco. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. At Gusto, we don't use titles the traditional way, as a signal of rank or hierarchy. Instead, our titles describe two things at once — your craft (what you do, e.g. Engineering, Design) and your scope of ownership (what you're accountable for) — which is why you'll see something like "Head of X" instead of a rank word like "Director" that tells you neither. Because of this, the title on this posting may look different from what you'd expect based on the scope and seniority of the role, and from how similar roles are typically titled elsewhere. If you have questions about how this role compares to your current title or level, your recruiter can help translate. 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. Reliable, consistent presence: We expect regular and predictable attendance, whether you're working in-office, hybrid, or fully remote, so that you stay closely connected to your team, customers, and stakeholders in real time and ensure colleagues and customers receive the timely support and responsiveness they deserve. 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.