Gusto

Senior Pricing and Monetization Manager

Gusto$152K — $218K *
US-AnywhereRemote in Toronto, ON
Finance & Insurance
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years of experience in fintech, SaaS, HR, payroll, or related fields
  • Strong analytical skills and attention to detail
  • Expertise in AI tools such as Claude.ai, Claude Code, and Cursor
  • Proven experience in executive relationship management and communication
  • Exceptional cross-functional stakeholder management abilities
  • Ability to adapt quickly in fast-paced environments
  • Curiosity and passion for pricing strategies

Responsibilities

  • Collaborate with Product, Finance, and Marketing to refine monetization strategies
  • Own and lead cross-functional commercial go-to-market projects
  • Transition the commercial strategy towards AI-driven solutions
  • Establish and track key Pricing and Monetization KPIs
  • Serve as the go-to expert for pricing and monetization matters
  • Engage with stakeholders like Product, Marketing, and Finance for impactful decision-making
  • Present complex pricing concepts to executives and senior leaders

Benefits

  • Hybrid work model with flexibility for remote work
  • Collaborative work environment with visible impact to leadership
  • Opportunities for professional growth and learning in AI
  • Involvement in innovative projects surrounding product and market strategies
Full Job Description
About the Role

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 ourplatform 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.
What You'll Do
  • 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 goes broad. 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 to our product and business.
What We're Looking For
  • 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, Claude Code, and Cursor.
  • A strong analytical mindset with strong 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 be presenting and working 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 towards 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
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
Compensation

Our cash compensation amount for this role is targeted at $152,000 - $180,000/yr in Denver, Phoenix, and Atlanta, and $180,000 - $218,000/yr for San Francisco & New York. The salary range for Toronto is CAD 133,000 - 160,000. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

#LI-Hybrid

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.

About Gusto

Gusto is a cloud-based human resources software platform that provides payroll, benefits, and HR management services to small businesses. The company was founded in 2011 and is headquartered in San Francisco, California. Gusto's platform automates many of the administrative tasks associated with HR, such as payroll processing, tax filings, and benefits administration. The company also offers a range of HR services, including compliance support, employee onboarding, and time tracking. Gusto is committed to helping small businesses succeed by providing them with the tools and resources they need to manage their HR operations more efficiently.
Learn more about Gusto
Size
1,000 employees
Industry
Founded
2012

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