Senior Pricing and Monetization Manager

Gusto Gusto · Fintech · Toronto, ON +2 · Remote · Marketing

This role is for a Senior Pricing and Monetization Manager at Gusto, a fintech company. The role focuses on developing and executing pricing and monetization strategies for Gusto's platform, including payroll, time management, HR, and financial services. While the company emphasizes an 'AI-native environment' and expects employees to use AI tools, the core responsibilities are product strategy, commercial go-to-market initiatives, and KPI management, rather than direct AI/ML model development. The role involves collaborating with various teams and shipping MVPs and pilots, indicating a focus on product delivery within an AI-enhanced workflow.

What you'd actually do

  1. 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.
  2. 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 goes broad. You will be asked to learn, adapt and grow your range of expertise.
  3. 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.
  4. Decide, Build, and Monitor the key Pricing and Monetization KPIs across our product and go-to-market portfolio.
  5. Be the pricing and monetization expert and go-to-partner for Monetization and Commercial strategy.

Skills

Required

  • Background in fintech, business banking, retirement, E-commerce, payroll, or HR back office SaaS
  • Background in B2B / B2C Saas in Payroll, HR, Fintech, ECommerce or related field.
  • 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](http://claude.ai), Claude Code, and Cursor.
  • A strong analytical mindset with strong attention to detail and creative problem-solving ability.
  • Executive relationship management and communication.
  • Exceptional cross-functional stakeholder management and relationship-building skills.
  • Clear, concise communicator, able to distill complex ideas for any audience
  • Thrives in fast-moving environments; able to pivot quickly and manage competing priorities

Nice to have

  • 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 underlying foundation coupled with ability to use AI to execute.
  • Familiarity with the latest AI tools to help with coding or data analytics tools such as Claude, Cursor, Gumloop

What the JD emphasized

  • AI-native environment
  • AI-powered builder program
  • ship MVPs, Proof of Concepts, and pilots right into market
  • building Agents instead of processes
  • use AI tools to conduct end-to-end technical data analysis