Director of Pricing & Monetization

Director of Pricing & Monetization

• Anywhere in Canada
• Remote
• Full-time

About Blue J

Blue J is the leading generative AI solution for tax professionals and one of Canada's fastest-growing AI companies. Headquartered in Toronto, we're a high-growth B2B SaaS company building industry-leading tax research software that helps accountants find accurate answers to complex tax questions with greater speed and confidence.

Backed by a $122M USD Series D funding round, we're scaling rapidly across North America and the UK while continuing to push the boundaries of what's possible with AI. By combining advanced technology with deep tax expertise, we empower tax professionals to work more efficiently, make better decisions, and deliver greater value to their clients.

A Note on Location

We are excited to meet with qualified candidates and are grateful for everyone's interest. This is a remote position open to candidates anywhere in Canada, with occasional travel to our Toronto office as needed. All candidates must be eligible to work in Canada.

To help you get off to a great start, we bring all new team members together for their first three days of onboarding. If you’re based outside of our local commuting area, Blue J will arrange and cover your travel and accommodation.

The Opportunity

Reporting to the VP, GTM Strategy & Operations, the Director of Pricing & Monetization will lead pricing and packaging analysis and recommendations at Blue J. You'll explore the questions that shape our commercial strategy:

• Who are our customers, and how do their needs differ?
• How do they get value from Blue J, and how should our pricing reflect it?
• How should our offering evolve as our product portfolio and customer base expand?

You’ll collaborate with Finance, Product, Sales, Customer Success, Marketing, and Revenue Operations, and regularly present recommendations to the executive team.

You’ll draw on experience in finance, FP&A, or a related analytical field to turn complex data into clear, actionable recommendations. You’ll build models, conduct analysis, and communicate findings to stakeholders with different perspectives and priorities, helping the team reach decisions and bring pricing and packaging changes to market.

What You’ll be Doing

Pricing & Packaging Strategy

• Lead analysis and develop recommendations for Blue J’s pricing and packaging structure, including plans, tiers, bundles, and add-ons.
• Evaluate how our pricing model can evolve as we launch new products and capabilities and serve a broader range of customer segments.
• Identify value metrics that align what customers pay with the value they receive.
• Develop principles and guidelines for discounting, promotions, renewals, and price changes.
• Build and maintain a prioritized monetization roadmap in partnership with GTM and Product leadership.

Financial Modeling & Analysis

• Build business cases and financial models to assess how pricing and packaging changes affect acquisition, conversion, expansion, retention, and customer lifetime value.
• Partner with Finance on revenue forecasting and scenario planning related to pricing decisions.
• Analyze deal, usage, and customer data to understand willingness to pay, actual prices paid, and discounting patterns.
• Measure the impact of pricing initiatives on annual recurring revenue (ARR) and margins, and share results with leadership.

Customer & Market Insights

• Develop segmentation frameworks based on customer needs, behaviours, and willingness to pay.
• Conduct qualitative and quantitative research, including customer interviews, surveys, win/loss analysis, and churn analysis, to test pricing assumptions.
• Monitor competitive pricing and SaaS and AI monetization trends, identifying developments relevant to Blue J’s strategy.

Experimentation & Implementation

• Design pricing and packaging experiments with clear hypotheses, success measures, and safeguards for customer trust and retention.
• Collaborate with relevant teams to implement approved changes across configure, price, quote (CPQ) systems, billing, and reporting.
• Develop rollout and transition plans for new and existing customers, and provide training and resources for Sales and Customer Success.
• Establish post-launch measurement plans and refine approaches based on results and feedback.

Cross-Functional Collaboration & Communication

• Establish a regular process for pricing reviews and decisions, with clear responsibilities across Finance, Product, and GTM.
• Present recommendations to executive leadership, clearly explaining the supporting evidence, trade-offs, and potential impacts.
• Advise Sales and Customer Success leadership on deal structures and pricing questions.

What You Offer Blue J

• 7+ years of experience in pricing, monetization, FP&A, strategic finance, or revenue strategy, ideally within B2B SaaS.
• Experience analyzing, recommending, and implementing pricing or packaging changes.
• Deep analytical and financial modeling skills, with a strong command of SaaS metrics and subscription economics (ARR, NRR, churn, CAC, LTV, gross margin).
• Experience with a range of pricing models, such as seat-based, usage- or consumption-based, value-based, and hybrid approaches.
• Comfort working directly with large datasets; proficiency in SQL and advanced spreadsheet modeling; experience with AI and BI tools.
• Ability to communicate findings and recommendations clearly in presentations and written communication, and collaborate with executives and teams across Blue J to reach decisions.
• Ability to evaluate commercial decisions by considering customer value, growth, and long-term strategy.
• Comfort operating autonomously in a fast-moving, high-growth environment where processes are still being built.
• Comfortable leveraging AI tools and emerging technologies to drive efficiency, improve workflows, and stay ahead of industry trends.

Nice To Have

• Experience supporting AI product monetization or designing and running pricing experiments.
• Experience supporting pricing or packaging as a company expands its product portfolio.
• Familiarity with configure, price, quote (CPQ) and billing systems.
• Experience in pricing consulting, an MBA, a CFA designation, or comparable practical experience.

What We Offer You

• A rare opportunity to own the pricing and monetization strategy at a fast-growing, well-funded AI company at a pivotal stage of its growth.
• A mission-driven culture where your work directly advances clarity, efficiency, and accessibility in tax research.
• Competitive base salary, stock options, and benefits designed to support you and your family.
• Flexibility in how you work primarily remote, with occasional travel to our Toronto office and conferences as needed.
• A collaborative, ambitious, and supportive team that values innovation, respect, and fun.
• The excitement of a fast-growing, well-funded company with clear momentum, and the resources to back bold initiatives.

The Core Values that Define Our Culture

• We are customer-focused
• We put team over self
• We are pleasant and playful
• We are open to better ideas
• We move fast and fix things

What to Expect in the Interview Process

We anticipate a high volume of applicants for this role and are excited to grow our team. A human will review each application and get back to you as soon as possible. We appreciate your patience and look forward to connecting with you!

Interview Process

• Chat with Natalie, Sr. TA Manager
• Meet Paul H. VP, GTM Strategy & Operations
• Meet Christine M. VP, Product Marketing
• Present your case study
• Meet Ben, our CEO

We believe our strength is built on diversity of thought, and encourage candidates from all backgrounds and experiences to apply. We value inclusiveness and are an equal opportunity employer. We do not discriminate based on race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

We strive to create an inclusive and accessible hiring experience for all candidates. If you need any accommodations during the interview process, please let us know in your application. Our team is dedicated to providing the necessary support and making reasonable adjustments to ensure a smooth process for everyone.

How We Use AI in Our Hiring Process

To ensure transparency, we want candidates to know that Blue J uses AI-enabled tools within our applicant tracking system to help organize applications and highlight profiles that match the key requirements for each role.

AI does not make hiring decisions.

Every application is reviewed by a member of our Talent team, and all decisions throughout the process are made by humans.

We use these tools to support efficiency and consistency, not to replace human judgment and we’re committed to a fair, thoughtful, and equitable experience for every candidate.

Compensation

The base pay range for this role is $165,000–$206,500 per year.

This is a Level 6 in Blue J’s career level framework. We use levels to define the expected scope, autonomy, impact, decision‑making, and experience for each role. Final compensation will be set fairly and thoughtfully based on experience, expertise, and alignment with the role’s responsibilities. While all candidates are expected to bring directly relevant experience, the top of the range is typically reserved for individuals who demonstrate exceptional depth in the role’s core competencies, a strong track record of impact in similar environments, and the ability to operate with a high degree of autonomy from day one.