Principal Product Manager – Monetization & Billing

Smartsheet•Bellevue, WA

22h•Remote

About The Position

For over 20 years, Smartsheet has helped people and teams achieve–well, anything. From seamless work management to smart, scalable solutions, we’ve always worked with flow. We’re building tools that empower teams to automate the manual, uncover insights, and scale smarter. But more than that, we’re creating space– space to think big, take action, and unlock the kind of work that truly matters. Because when challenge meets purpose, and passion turns into progress, that’s magic at work, and it’s what we show up for everyday. Corporate Systems Engineering builds and operates the software platforms, integrations, and automations that power Smartsheet’s core business functions across Finance, Sales/GTM, and People & Culture. Our team owns mission-critical systems and workflows that enable how the company hires, sells, bills, pays, reports, and scales. We operate at the intersection of software engineering, enterprise platforms, and business-critical data, treating internal systems with the same rigor, reliability, and product mindset as customer-facing software. Corporate Systems Product Management focuses on the internal platforms that power how Smartsheet operates - including Finance, People, Sales operations, integrations, and internal automation. Product Managers in this team steward system roadmaps, business workflows, and long-term platform evolution across these domains. As Principal Product Manager – Monetization & Billing, you will own the end-to-end systems and workflows that define how Smartsheet monetizes its products. This includes subscriptions, usage-based pricing, consumption models, entitlements, provisioning, billing, and the integration of these capabilities across product, GTM, and finance systems. You will operate at the intersection of Product Engineering, Sales/GTM, and Finance to ensure monetization models are accurately represented, scalable, and adaptable as the business evolves. This role is responsible for shaping how pricing and packaging strategies are translated into system capabilities, ensuring consistency from quote through provisioning, billing, and revenue recognition. You will partner closely with Product Engineering, Sales Operations, Finance, and Integration teams to steward system health and define the future state of Smartsheet’s monetization architecture as new pricing paradigms and business models emerge. You will report to the Director of Corporate Systems Product Management and collaborate closely with Engineering and senior business stakeholders across the company. This full-time position reports to the Sr. Director, Development and can be located in our Bellevue, WA office, or you may work remotely from anywhere in the US where Smartsheet is a registered employer.

Requirements

Bachelor’s degree in Business, Information Systems, Computer Science, or a related field — or equivalent practical experience. An advanced degree is a plus but not required.
8+ years of experience supporting enterprise systems as a Product Manager, Systems Analyst, or similar role, with increasing ownership and scope
Strong experience working within Order-to-Cash, billing, subscription, or monetization systems in a SaaS environment
Deep understanding of SaaS business models including subscriptions, usage-based pricing, consumption models, and revenue workflows
Experience working across multiple enterprise systems such as Salesforce, billing platforms, and financial systems
Strong systems thinking and ability to design and reason about complex cross-system workflows and data flows
Experience translating evolving business models into scalable system capabilities
Ability to operate at both strategic and tactical levels, defining vision while driving execution
Strong prioritization skills and comfort balancing business flexibility, technical constraints, and operational risk
Excellent analytical and both verbal and written communication skills with the ability to influence senior stakeholders
Legally eligible to work in the U.S. on an ongoing basis

Nice To Haves

Experience supporting or enabling new pricing paradigms, monetization strategies, or platform transformations is strongly preferred

Responsibilities

Own the product vision, roadmap, and prioritization for Order-to-Cash and monetization platforms across Smartsheet
Define how pricing, packaging, and monetization models (subscription, usage-based, consumption, multi-year agreements) are implemented across systems
Partner closely with Product Engineering, Sales Operations, and Finance stakeholders to understand monetization workflows, constraints, and opportunities
Steward the end-to-end lifecycle from quote to provisioning to billing to revenue alignment across systems
Define and evolve entitlement and provisioning models that connect the core product platform with GTM and billing systems
Ensure reliable integrations and data flows across Salesforce, product platforms, billing systems, and financial systems
Translate complex monetization and pricing requirements into clear system-level decisions, tradeoffs, and prioritization
Balance flexibility for new business models with system integrity, auditability, and operational simplicity
Identify and resolve inconsistencies, inefficiencies, and risks across monetization workflows and system boundaries
Partner with Engineering teams to design scalable, integration-driven solutions that support evolving SaaS and AI-driven business models
Establish and monitor metrics that track monetization system health, accuracy, and operational performance
Communicate roadmap direction, tradeoffs, and system constraints clearly to senior leadership and stakeholders
Support governance, readiness, and lifecycle planning for monetization-related system changes and enhancements

Benefits

Employer subsidized medical/vision and dental coverage for full-time employees
401k Match to help you save for your future (50% of your contribution up to the first 6% of your eligible pay)
Monthly stipend to support your work and productivity
Flexible Time Away Program, plus Sick Time Off
US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans
US employees receive 12 paid holidays per year
Up to 24 weeks of Parental Leave
Personal paid Volunteer Day to support our community
Opportunities for professional growth and development including access to Udemy online courses
Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account
Teleworking options from any registered location in the U.S. (role specific)
Smartsheet provides a competitive base salary range for roles that may be hired in different geographic areas we are licensed to operate our business from. Actual compensation is determined by several factors including, but not limited to, level of professional, educational experience, skills, and specific candidate location. In addition, this role will be eligible for a market competitive incentive opportunity.