Director of Pricing & Monetization

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 number of factors including market location, job-related knowledge, skills/competencies and experience.

Your recruiter can share more about the specific offerings for this role, as well as the salary range for your primary work location during the hiring process.

**This role is expected to come into our Toronto office 2 days a week, so you can thrive in your new role and fully embrace being a Dutonian!**