Best suited to B2B SaaS professionals with 10+ years in product monetization who thrive in cross-functional leadership roles.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from PagerDuty via Greenhouse
PagerDuty (NYSE:PD) is a leader in Digital Operations Management. In an always-on world, organizations of all sizes trust PagerDuty to help them deliver a perfect digital experience to their customers, every time. Teams use PagerDuty to identify issues and opportunities in real time and bring together the right people to fix problems faster and prevent them in the future. Over 13,000 organizations (including 60 of Fortune 100) rely on PagerDuty to succeed with Digital Transformation, Cloud Migration, and DevOps Modernization. Notable customers include GE, Cisco, Genentech, Electronic Arts, Cox Automotive, Netflix, Shopify, Zoom, DoorDash, Lululemon and more. We are expanding rapidly as a platform for Digital Operations Management using AI/ML and Automation and growing our adoption by Development, IT, Customer Service, Security, and other teams across the organization.
About the Role
PagerDuty is seeking a Director of Pricing & Monetization to own the strategy and execution of how we package, price, and monetize our Operations Cloud platform. This role sits within our Product Development organization and reports to the VP of Product Strategy & Growth.
This is a product-first role. You'll bring the same rigor to pricing that a great PM brings to a product: deep customer empathy, structured experimentation, clear feature tiering frameworks, and a bias toward measurable outcomes. You'll also be the connective tissue between Product, Sales, Finance, and Marketing, ensuring pricing strategy translates into field execution and commercial results. This role owns the full lifecycle from recommendation to implementation to operations. You'll be the decision-maker on deal desk, discounting, and promotions in real-time.
The ideal candidate has operated at the intersection of product management and monetization in a later-stage B2B SaaS environment. You've owned packaging decisions end-to-end, built monetization infrastructure, and have the credibility to influence both product roadmaps and sales motions.
What You'll Own
Product & Monetization
Define and evolve PagerDuty's packaging architecture — tiers, feature placement, usage-based levers, and entitlement frameworks — in partnership with Product and Engineering
Build and maintain a monetization review process so product teams bring pricing strategy into roadmap decisions early, not as an afterthought
Lead SKU design and experimentation: develop frameworks for how we create, test, and iterate on packaging changes quickly and safely
Own the monetization platform roadmap — usage tracking, entitlement flexibility, SKU experimentation velocity — in partnership with Engineering and Revenue Systems
This person is the cross-functional decision-maker across product, design, and engineering for what we build (including feature frameworks, entitlements, and metering) for how we take products to market. Owning the full lifecycle across plan to execution and operations
Provide pricing and packaging leadership to other product teams across the portfolio
Go-to-Market Execution
Operationalize pricing for the field: discount governance, approval workflows, customer-facing messaging, and enablement materials
Lead packaging migration execution as we transition legacy customers to our modern Operations Cloud plans — including cohort strategy, field playbooks, and customer communication
This person is expected to be a cross-functional decision-maker for GTM, Technology, and Revenue Operations teams
Feedback, Analysis, and Planning
Track and report on pricing initiative performance — win rates, discounting patterns, migration progress, ARR impact by segment
Build or leverage financial modeling capabilities (in partnership with Finance) to evaluate pricing scenarios and segment-level impact
Get in front of customers regularly to pressure-test pricing assumptions and surface friction points
What You'll Build
This role inherits and grows an existing pricing and monetization foundation that includes:
Billing & quoting infrastructure — core systems supporting deal execution and revenue operations, with opportunity to improve velocity and flexibility in partnership with Engineering and Revenue Systems
Pricing calculators and field tools — internal tools used by the field to size and quote deals, currently in active development
Discount approval workflows — existing governance structure for deal-level pricing decisions
SKU architecture — a portfolio of plans spanning our legacy and modern Operations Cloud offerings, currently mid-migration
Partner with executive leadership to align pricing strategy with company-level ARR and growth targets
The opportunity is to modernize this foundation so pricing decisions and actions happen faster, and go-to-market teams have tools they trust and actively use.
You'll lead and grow an existing small team:
Pricing Analyst — supporting financial modeling and plan analysis
Pricing Manager — focused on SKU migrations and pricing execution
Technical PM / Monetization Ops — scaling infrastructure work
Your job is to elevate this team from execution support to a strategic pricing function that product and sales teams actively seek out. We're looking for people who have...
Basic Qualifications
10+ years in B2B SaaS in roles spanning product management, pricing strategy, and/or monetization
Demonstrated experience owning packaging architecture and feature tiering decisions — not just supporting them
Track record of running pricing experiments and measuring commercial impact
Strong cross-functional credibility with Sales, Finance, Product, and Go-To-Market leadership
Experience managing pricing change in the field — migrations, repackaging, new monetization models — with the communication skills to bring stakeholders along
Ability to mentor and grow other pricing and product roles
Preferred Qualifications
Experience at a company during transition to usage-based or consumption pricing
Familiarity with monetization infrastructure (entitlements, billing systems, SKU tooling)
Familiarity with B2B SaaS deal structures, discount governance, and revenue recognition considerations
Has led or contributed to pricing strategy at a company scaling toward $1B+ ARR
What Success Looks Like
3 months
Deep understanding of current SKU architecture, billing systems, and field pricing dynamics
Relationships established with Sales Strategy, Deal Desk, Finance, and key Product leaders
Monetization review process proposed — ensuring product teams bring pricing decisions forward early
6 months
1–2 packaging experiments launched and instrumented (e.g., new tier, usage-based pilot, feature unbundling)
Go-to-market and customer-facing pricing tools meaningfully improved — measurable increase in field confidence and usage
Discount governance strengthened — clear ownership and sign-off process for deal-level exceptions
SKU creation process improved — clear ownership, documented process, and faster turnaround
12 months
Measurable ARR impact: improved win rates on Operations Cloud, reduced discounting frequency, or accelerated legacy SKU migration progress
Monetization infrastructure roadmap in flight — billing and quoting systems have a credible modernization path
Entitlement flexibility improved — product teams can run pricing experiments with greater speed and independence
Pricing function is seen as a strategic partner across Product, Sales, and Finance
Team is performing with high agency and developing toward expanded scope
The base salary range for this position is 156,000 - 236,500 CAD. This role may also be eligible for bonus, commission, equity, and/or benefits.
Our base salary ranges are determined by role, level, and location. The range, which is subject to change based on primary work location, reflects the minimum and maximum base salary we expect to pay newly hired employees for the position. Within the range, we determine pay for an individual based on a n
Source: PagerDuty careers (Greenhouse)