Pricing Operations Principal

About the Team OpenAI Finance ensures the organization is positioned for long-term success as we pursue our mission. The Revenue team plays a critical role in enabling OpenAI to scale commercial offerings by overseeing billing operations, deal desk, revenue systems, revenue accounting, and controllership. We work cross-functionally with Product, Engineering, Go-To-Market, Tax, Legal, and Technical Accounting to support new monetization strategies, improve operational efficiency, and maintain financial integrity as the business grows. About the Role This senior leader will own key elements of Ads revenue accounting from technical assessment through operational execution. The role will guide accounting for products, pricing, contracts, incentives, credits, refunds, makegoods, international expansion, and new go-to-market motions. It will establish governance and translate approved accounting positions into launch, billing, data, close, reconciliation, and control requirements. Success requires deep technical revenue expertise, strong business partnership, and the ability to build durable 0-to-1 processes in a fast-changing environment. Advertising is a critical and growing monetization vector for OpenAI, and this role will help shape the financial foundations that enable Ads to scale responsibly and transparently. This role is based in San Francisco, CA. We use a hybrid work model of 3 days in the office per week and offer relocation assistance to new employees. In this role, you will: Lead technical accounting assessments for Ads products and commercial arrangements, including performance obligations, variable consideration, allocation, principal-versus-agent, collectibility, contract modifications, refunds, incentives, credits, makegoods, and revenue presentation. Own and continuously evolve Ads revenue accounting policies and operating guidance as product behavior, pricing, contracting, incentive programs, and billing models change. Establish governance for new pro

About the role As a Pricing Strategist focused on GTM, you will help shape pricing strategy for B2B enterprise customers across our product portfolio. Working within Finance and partnering with GTM, Sales, and Product, you will focus on pricing analytics, price performance, and the effectiveness of credit programs while contributing to broader commercial strategy. In this role, you will Build regular pricing-performance reviews, analyze discounting and concessions, and turn findings into better pricing guidance. Develop commercial strategies and pricing programs for customer segments such as education, startups, and government. Define objectives and success measures for credit programs and promotions, and evaluate their return on investment. Translate segment goals and product pricing strategy into scalable pricing frameworks and commercial structures. Partner on strategic enterprise deals to align commercial proposals with sound deal economics and pricing strategy. You might thrive in this role if you Approach problems from first principles, identify root causes, and develop clear options for stakeholders. Work effectively through ambiguity and differing perspectives. Understand how sales organizations operate and collaborate well across GTM strategy, Finance, and Product. Bring relevant experience from consulting, strategy and operations, or pricing, particularly work involving analytical teams. Experience with pricing analytics, pricing frameworks, discounting guardrails, or new-product pricing is helpful, but a strictly pricing-specific background is not required. About OpenAI OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. We push the boundaries of the capabilities of AI systems and seek to safely deploy them to the world through our products. AI is an extremely powerful tool that must be created with safety and human needs at its core, and to achieve our mission, we mu

As a Senior Deal Desk Analyst, you will work cross-functionally with our Sales Operations, Billing, Contracts and Legal teams to provide quoting and deal structuring support to the Global Sales Team. This will be a growth position as Datadog’s business continues to expand. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them What You’ll Do: Develop in-depth knowledge of Datadog’s licensing and pricing models to provide deal structuring and quoting support to our global sales teams Be a creative problem solver who finds a way to meet customers’ needs while adhering to Datadog’s selling policies Solve customer satisfaction issues following execution of the deal Actively negotiate deals directly with the customer as needed Work cross functionally across various stakeholder groups including legal, contracts, sales operations, order management, revenue, finance and product management Function as point of contact and subject matter expert for Sales on deal pricing matters Drive adherence to internal controls, protocols and business rules Who You Are: Experienced in 4+ years of Deal Desk experience Confident in deal structuring/quoting complex SaaS transactions for a fast-growing global company Knowledgeable of revenue recognition principles Comfortable representing the company to customers in negotiations and resolving customer satisfaction issues Strong in your attention to detail and communication skills Able to work independently and multi-task in fast paced, high pressure environment Data-driven with strong quantitative skills Analytical with the ability to approach a problem from multiple perspectives Bonus Points: Experience with Salesforce and CPQ Advance level with MS Excel or similar. Datadog values people from all walks of l

About Flexport: At Flexport, we believe global trade can move the human race forward. That’s why it’s our mission to make global commerce so easy there will be more of it. We’re shaping the future of a $10T industry with solutions powered by innovative technology and exceptional people. Today, companies of all sizes—from emerging brands to Fortune 500s—use Flexport technology to move more than $19B of merchandise across 112 countries a year. The recent global supply chain crisis has put Flexport center stage as we continue to play a pivotal role in how goods move around the world. We are proud to have the support of the best investors in the game who believe in our mission, solutions and people. Ready to tackle global challenges that impact business, society, and the environment? Come join us. The opportunity Join the Office of the CEO and work directly on Flexport's highest-priority problems alongside the CEO, the President, and the leaders who run our regions and modes of freight. You will pick up a mode or a region, ocean, air, trucking, omnichannel, or customs, and learn it from the inside by solving real problems in it. Pricing in a mode that is losing money. Why a region misses its plan. Whether we buy, build, or partner. Then you go run part of it. Some people in this role move into a business unit as the number two to the leader who runs it. Some stay at the center and take on more scope. The operating job at the end is the point of the role, not a side benefit. You will: Own our biggest open questions end to end and come back with recommendations the CEO can act on. Build the analysis yourself. Pull the data, build the model, find the error before someone else does. Go to where the work happens, from warehouses and ports to a customer's supply chain team. Opinions about freight formed in a conference room are usually wrong. Run the operating cadence for a freight mode or region. Weekly metrics, quarterly plan, and the follow-ups nobody wants to

About the Team OpenAI's Professional Services team helps organizations move from AI ambition to durable production outcomes. We partner with customers on complex deployments and build the strategy, commercial models, operating mechanisms, and delivery capacity needed to realize value from OpenAI's models and products. The team works across Go-to-Market, Forward Deployed Engineering, Technical Success, Finance, Product, Legal, Data, Systems, and delivery partners. We are building a services motion that is customer-centered, commercially rigorous, operationally scalable, and deliberately connected to product adoption. About the Role We are seeking a senior GTM Strategy & Operations professional to build and scale the operating system for OpenAI's Professional Services business. This is a foundational, hands-on individual contributor role at the intersection of business strategy, finance, go-to-market, and delivery. You will turn ambiguous questions—what we offer, how we price and package it, how we plan capacity, and how we measure performance—into clear decisions and repeatable mechanisms. You will own business planning, pricing and packaging, forecasting and modeling, management reporting, and cross-functional strategic initiatives. You will build integrated views of demand, staffing, revenue, margin, and delivery performance; replace one-off analyses with durable processes; and create operating cadences that help leaders act early. You will be a trusted partner to Professional Services, GTM, FDE, Technical Success, Finance, Product, Legal, Revenue Operations, and Data leaders. The right person combines direct Professional Services judgment with rigorous analytics, executive communication, and the willingness to build the model, process, or dashboard themselves. You’ll be responsible for: Define and drive the business and GTM strategy for Professional Services, including target customer needs, offer portfolio, positioning, pricing and packaging, partner motions,

About the Team The Pricing & Monetization team is responsible for how our products create and capture value. We partner closely with Product, GTM, and Finance to design pricing models, packaging, and commercial strategies that support adoption, growth, and long-term scaling of the business. To thrive on this team, you need to be a proactive problem-solver who excels at bringing structure to ambiguous challenges. Our work demands strategic thinking, cross-functional collaboration, and precision in execution. Team members succeed when they are analytical, detail-oriented, skilled at balancing multiple priorities, and passionate about driving high-stakes projects forward to deliver meaningful results. About the Role We are looking for a Pricing Strategist with hands-on consumer pricing experience to shape how we price, package, and monetize our products across our consumer offerings. You’ll work closely with senior leaders across Product, GTM, and Finance to define pricing approaches, improve commercial decision-making, and bring more rigor to how we monetize our offerings. You should be comfortable building monetization frameworks and commercial policies, analyzing tradeoffs, supporting and driving high-impact decision-making. You should also care deeply about the customer perspective and believe that strong pricing reflects a real understanding of customer value, needs, and friction points in order to build pricing that is clear, fair, and aligned with how customers experience our products. This role will report to the Head of Product Pricing for Chat & Codex. What you’ll do Develop pricing and packaging strategy across subscription tiers, usage limits and entitlements, credits and overages, and emerging monetization models, balancing customer value, growth, and unit economics. Develop innovative commercial constructs to better serve our customers. Partner with Product, GTM, and Finance leaders to ensure pricing aligns with product value, the roadmap, commerc