Business Operations Manager, Monetization (Product-Led Growth)

About Rippling

Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system.

Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds.

Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes.

We prioritize candidate safety. Please be aware that all official communication will only be sent from @Rippling.com addresses.

About the role

As a founding member of our new Monetization & Pricing Team within BizOps, you will own pricing and packaging strategies across our expanding product portfolio. This role will be focused on our Product-Led Growth (PLG) monetization motion, optimizing self-serve funnels, freemium-to-paid conversions, and paywall strategies across our suite of AI, HR, IT, and Spend products.

What you'll do

• Drive PLG monetization strategy: Work in partnership with Product, Growth, Marketing, and Engineering to design and optimize self-serve pricing tiers, free trial experiences, and freemium models that reduce friction and accelerate a user's time-to-value.
• Optimize monetization triggers: Determine the optimal pricing levers, capacity limits, and paywall interventions that prompt self-serve upgrades. Partner with Sales to price the "bridge" between self-serve usage and enterprise contracts, ensuring a frictionless commercial upgrade path.
• Conduct Deep Analysis: Lead quantitative and qualitative research—such as high-velocity A/B price testing, willingness-to-pay (WTP) studies across user cohorts, and price elasticity analysis—to optimize self-serve price points and packaging variations at scale.
• "Go and see": Immerse yourself in the buyer journey by analyzing self-serve checkout telemetry, conducting tear-downs of competitor pricing pages, interviewing users who abandoned the upgrade flow, and working directly with Growth R&D to understand monetization friction firsthand.
• Balance Cross-Functional Needs: Act as the unbiased connective tissue between Product Growth, Go-To-Market, and Finance, facilitating open debate and challenging stakeholders directly to arrive at the best decision for Rippling.

What you will need

• 6+ years of experience in a growth, pricing, business operations, management consulting, venture capital, or founder role—with a strong focus on Product-Led Growth (PLG) monetization and self-serve SaaS funnels. We will consider high-trajectory candidates with fewer years of experience but at top companies with a clear track record of excellence.
• Deep PLG Acumen: A strong understanding of bottom-up SaaS business models and key PLG metrics (Activation Rates, Time-to-Value, PQL conversion, self-serve retention, LTV/CAC, and expansion loops).
• Naturally Analytical Mindset: You gravitate toward a spreadsheet and product analytics dashboards rather than a slide deck. Experience with SQL, product analytics tools (e.g., Amplitude, Mixpanel), and A/B testing frameworks is highly preferred.
• Cross-Functional Fluency: Experience in a highly cross-functional role with the ability to clearly describe and work within the organizational dynamics of a fast-growth company, specifically bridging the gap between Product and Sales.
• Altitude Agility: Ability to operate at all altitudes – from discussing PLG vision and board-level strategy with executives, to troubleshooting paywall logic and self-serve billing operations with individual contributors.
• Extreme Ownership: An extreme degree o