Staff Product Manager, Monetization

About the team & opportunity

What’s so great about working on Calendly’s Product team? 

We strive to design a seamless product experience that delights our customers.

Why do we need you? Well, we are looking for a Staff Product Manager, Monetization that is customer focused with a passion for experimentation, human-centered customer journeys, and connecting product led growth initiatives back to the business. This position will report to our Senior Director of Core Product.

A day in the life of a Staff Product Manager at Calendly

As a Staff Product Manager at Calendly, you will be responsible for driving strategic pricing and packaging experimentation within our SaaS environment. Your work will leverage product-led growth (PLG) principles to craft product experiences that clearly demonstrate the value of Calendly, foster customer engagement, and ultimately drive conversion, expansion, and long-term business growth.

You will work closely with cross-functional teams, including Engineering, Design, Marketing, Customer Success, and Product leadership, to align on growth, product outcomes, and customer satisfaction goals. Your primary focus will be to optimize our pricing and packaging strategies through data-driven experimentation, ensuring they align with our business model and drive both new customer acquisition and expansion revenue.

Some of the initiatives you will shape may include:

• Leading and experimenting with pricing and packaging strategies to optimize customer acquisition and expansion, including conducting A/B testing and iterating on various pricing models
• Driving the integration of product-led monetization strategies with various sales-led motions
• Owning and continuously optimizing the trial mechanics and user journey, ensuring alignment with pricing changes to maximize conversions and drive sustainable growth

On a typical day, you will be working on:

• Collaborating with Finance to refine and evolve Calendly’s pricing & packaging models, ensuring they are scalable, competitive, and aligned with product-led acquisition and expansion motions
• Partnering with Engineering, Design, and Product teams to identify and prioritize technical investments in our billing and monetization platform, enabling future scaling and experimentation
• Leading cross-functional teams through data-informed experiments, measuring their impact on customer behavior, pricing sensitivity, and overall business metrics
• Designing and delivering growth experiments based on quantitative and qualitative insights, working closely with data teams to validate pricing hypotheses and improve revenue models
• Staying current on industry best practices related to SaaS pricing strategies, PLG methodologies, and product-led monetization approaches
• Identifying and resolving friction points across the user journey, improving conversion rates and expanding product-led revenue streams

What do we need from you?

• 8+ years of experience in growth product management, with significant expertise in SaaS pricing & packaging experimentation
• Location Preference: Candidates based in the San Francisco Bay Area are strongly preferred for this role
• Proven track record in developing and executing pricing and packaging strategies in a B2B or B2B2C SaaS environment
• Deep understanding of SaaS metrics such as Net Dollar Retention (NDR) and Gross Dollar Retention (GDR), and the ability to connect them to pricing decisions and growth strategies
• Experience with data analytics and hypothesis-driven experimentation, specifically in pricing optimization, A/B testing, and packaging strategies
• Strong ability to collaborate with cross-functional teams (Finance, Engineering, Product, Marketing) to drive the implementation of pricing & packaging changes at scale
• Experience in building and evaluating growth metrics, and using data to inform decisions on customer acquisition, activation, monetization, and retention
• Expertise in identifying friction points in customer journeys and optimizing user flows to drive conversions and revenue growth
• Ability to thrive in an ambiguous environment and make informed decisions based on partial data, balancing experimentation with business goals
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

What’s in it for you?

Ready to make a serious impact? Millions of people already rely on Calendly’s products, and we’re still in the midst of our growth curve — it’s a phenomenal time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional career.

If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please contact us at [email protected] . 

Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Hawaii, Montana, North Dakota, South Dakota, Nebraska, Iowa, West Virginia, and Rhode Island, you will not be eligible for employment. Note that all individual roles will specify location eligibility.

All candidates can find our Candidate Privacy Statement here

Candidates residing in California may visit our Notice at Collection for California Candidates here: Notice at Collection

The ranges listed below are the expected annual base salary for this role, subject to change.

Calendly takes a number of factors into consideration when determining an employee’s starting salary, including relevant experience, relevant skills sets, interview performance, location/metropolitan area, and internal pay equity.

Base salary is just one component of Calendly’s total rewards package. All full-time (30 hours/week) employees are also eligible for our Quarterly Corporate Bonus program (or Sales incentive), equity awards, and competitive benefits.

Calendly uses the zip code of an employee’s remote work location, or the onsite building location if hybrid, to determine which metropolitan pay range we use. Current geographic zones are as follows:

• Tier 1: San Francisco, CA, San Jose, CA, New York City, NY
• Tier 2: Chicago, IL, Austin, TX, Denver, CO, Boston, MA, Washington D.C., Philadelphia, PA, Portland, OR, Seattle, WA, Miami, FL, and all other cities in CA.
• Tier 3: All other locations not in Tier 1 or Tier 2