Senior Pricing and Monetization Manager

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.

Our Product Pricing & Monetization team sits at the intersection of product and commercial strategy, responsible for holistic pricing and packaging across Gusto's full product suite.

We're looking for a Senior Pricing and Monetization Manager to focus across our entire platform portfolio including Gusto Payroll, Gusto Time management and HR, and our suite of embedded financial services for employers and employees. You’ll collaborate closely with product, sales, marketing, data, engineering, and finance, with work that is visible to Gusto leadership.

• Work in partnership across Product, Finance, Marketing, and Go-to-Market to review and recommend monetization and pricing strategies for new product launches and our existing portfolio.
• Be a world‑class operator, owning and delivering on cross‑functional projects and commercial go‑to‑market initiatives. In an AI‑native environment, strategy, ownership, and execution will broaden. You will be asked to learn, adapt, and grow your range of expertise.
• Help shift from a commercial strategy and operations function to an AI‑powered builder program. You’ll ship MVPs, Proof of Concepts, and pilots right into market.
• Decide, build, and monitor the key Pricing and Monetization KPIs across our product and go‑to‑market portfolio.
• Be the pricing and monetization expert and go‑to‑partner for Monetization and Commercial strategy.
• Work closely with key stakeholders such as Product, Product Marketing, Sales, Data Science, and Finance. Products will have direct executive line‑of‑sight and direct impact on our product and business.

• Background in fintech, business banking, retirement, e‑commerce, payroll, or HR back‑office SaaS.
• Experience in B2B/B2C SaaS in Payroll, HR, Fintech, or related fields.
• An AI‑native operator who can go from strategy to execution quickly, building agents instead of processes. You’ll be an expert in Claude.ai, Claude Code, and Cursor.
• A strong analytical mindset with attention to detail and creative problem‑solving ability. Able to use AI tools to conduct end‑to‑end technical data analysis.
• Executive relationship management and communication. You’ll present and work on topics for our executives, board, and senior leaders across Gusto.
• Exceptional cross‑functional stakeholder management and relationship‑building skills. Your success will be defined by your ability to move a broad set of stakeholders toward a common goal.
• Clear, concise communicator, able to distill complex ideas for any audience.
• Thrives in fast‑moving environments; able to pivot quickly and manage competing priorities.
• Curious, growth‑oriented, and genuinely passionate about pricing.

• Experience developing and delivering pricing and go‑to‑market recommendations in product, marketing, finance, or consulting.
• Experience with technical pricing research, like conjoint or max‑diff analysis, or other quantitative research techniques.
• Expertise in technical data analysis skills, like SQL, Python, or R. Expect a foundation coupled with the ability to use AI to execute.
• Familiarity with the latest AI tools to help with coding or data analytics, such as Claude, Cursor, Gumloop.

Our cash compensation for this role is targeted at $152,000‑$180,000/yr in Denver, Phoenix, and Atlanta; $180,000‑$218,000/yr in San Francisco & New York; and CAD 133,000‑160,000 in Toronto. Final offer amounts are determined by multiple factors including candidate experience and expertise.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees 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 the role). The same office expectations apply to all Symmetry roles, Gusto's…