Commercial Lead, Enterprise

About the Team OpenAI’s Finance and Revenue Operations organization builds the commercial infrastructure that enables the business to scale with speed, discipline, and financial integrity. Within Revenue Operations, Deal Desk partners closely with Sales, Partnerships, Product, Engineering, Legal, Technical Revenue, Finance, Billing, Order Management, and GTM Systems to turn complex commercial opportunities into executable, scalable transactions. About the Role We are hiring a Strategic Deals & Commercial Architecture Lead — Marketplaces & Partnerships to own the commercial architecture, execution, and governance layer for marketplace-enabled and partner-led transactions. This senior individual-contributor role is for someone who combines enterprise deal judgment, marketplace fluency, analytical rigor, and a builder mindset. You will take shaped opportunities from intake through approval and launch readiness, translating first-of-kind structures into clear economics, executable terms, quote-to-cash requirements, controls, and operating mechanisms. You will partner closely with teams that own business development and partner relationships; this role does not own partner sourcing, pipeline generation, or sales closing. You will support the commercial requirements for onboarding and integration without owning technical delivery. Success is measured both by the decisions and deals you enable and by the durable policies, systems, and controls you leave behind. This role is based in San Francisco, CA. We use a hybrid work model of three office days per week and offer relocation assistance. In This Role, You Will Lead the commercial architecture and execution of complex marketplace-enabled and partner-led enterprise transactions from intake through approval, contracting, launch readiness, and operational handoff. Structure private offers, pricing, fees, incentives, commitments, revenue share, credits, renewals, amendments, and other non-standard or multi-party terms

About the Team OpenAI’s Finance and Revenue Operations organization builds the commercial infrastructure that enables the business to scale with speed, discipline, and financial integrity. Deal Desk operates as the commercial strategy and governance function at the intersection of Sales, Partnerships, Legal, Technical Revenue, Finance, Order Management, Billing Operations, Product, and GTM Systems. We architect complex enterprise transactions, turn ambiguity into executable decisions, and create the guardrails that let the business move quickly with operational and financial discipline. As OpenAI’s enterprise business grows in scale and complexity, Deal Desk defines how novel commercial motions become durable operating capabilities. We convert precedent-setting deal decisions into repeatable policy, controls, workflows, and systems requirements. About the Role We are hiring a Strategic Deals & Commercial Architecture Lead to lead the structuring and governance of OpenAI’s most complex enterprise transactions. This is a senior individual-contributor leadership role for someone with exceptional enterprise deal judgment, operational rigor, and a builder mindset. You will serve as the commercial architect for high-stakes opportunities, translating ambiguous requirements into coherent deal structures, approval strategies, and executable quote-to-cash plans. Your work will shape more than individual transactions. You will establish decision principles and precedent, clarify tradeoffs, and turn recurring patterns into scalable guidance, controls, systems requirements, and enablement. You will own the commercial decision and governance layer that helps strategic opportunities move decisively while managing downstream risk across contracting, billing, revenue recognition, provisioning, reporting, controls, auditability, and customer experience. The right candidate can move seamlessly between advising on a single high-value transaction and improving the operating model be

About the team OpenAI’s mission is to build safe artificial general intelligence (AGI) that benefits all of humanity. Achieving this requires bringing together world-class scientists, engineers, and business leaders to translate frontier research into real-world impact. Within OpenAI, the Go-to-Market organization helps customers understand, adopt, and scale our products across their businesses. The team includes Sales, Solutions, Support, Marketing, Partnerships, and Strategic Pursuits professionals who work together to bring the benefits of AI to organizations globally. About the role We are hiring a Senior Specialist Seller to join the Strategic Pursuits team and lead priority opportunities generated through the joint AWS and OpenAI co-sell motion. You will partner closely with Account Directors, AWS field teams, and cross-functional stakeholders to identify, shape, advance, and close high-value strategic enterprise engagements. This role is ideal for a senior seller with deep experience in enterprise technology, AI, cloud, or complex transformation sales motions. You should be comfortable operating in executive-facing environments, aligning multiple stakeholders, and turning customer priorities into commercially compelling and technically credible opportunities. This role is based in San Francisco, Seattle, or New York. We operate on a hybrid model of 3 days per week in office and offer relocation support. We are also open to remote candidates based in the United States. In this role, you will: Lead commercial execution of priority AWS/OpenAI co-sell opportunities across strategic enterprise accounts. Identify and qualify high-potential opportunities focused on GenAI adoption, frontier platform use cases, and enterprise-wide transformation. Partner with AWS and OpenAI field teams to align account strategy, messaging, stakeholder mapping, and execution plans. Develop customer-facing value propositions that connect OpenAI capabilities with business priorities and

About Decagon Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences. Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel. We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others. We’re an in-office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team. About the Role Decagon is looking for someone to join the Business Operations & Strategy team to lead commercial and pricing strategy. The Business Operations & Strategy team sits within the Founder’s Office, a team of high-agency generalists and ex-founders with extremely high leverage and own things like partnerships, business development, pricing strategy, AI transformation, data/analytics, growth, etc. Your primary goal will be to accelerate and streamline our enterprise go-to-market motion - working closely with our GTM team to close deals. Initiatives will range from developing pricing & packaging strategy, to building internal deal and pricing processes, to proposal creation and negotiation across our enterprise customer base. This is an exciting role blending strategic thinking and high-caliber execution. We are looking for highly-motivated problem solvers who combine analytical rigor with world-class relationship building skills. In this role, you will Work to develop and refin

Who We Are Notion is the collaborative AI workspace where teams and agents think together . We're building one place where your knowledge, projects, meetings, and AI tools live side by side, so work is faster, clearer, and less fragmented. Millions of individuals, small teams, and large companies run their work on Notion. Notinos (our employees) are customer zero in bringing this future of work to life. We care about craft, building things that last, and the belief that great work is still fundamentally human. Our goal isn’t to ship the next feature. Each and every team of Notinos is working to set the standard for how humans work together in the AI era. From building a business’s system of record to making and managing AI agents to automating away the busy work, we care deeply about giving our customers more time for their life’s work. About the Role: As our GTM Compensation Lead on Commercial Operations, you’ll own commissions strategy, design, and execution for GTM. This is an opportunity to evolve how GTM Comp supports a growing GTM org through Notion’s AI-era selling motion and Enterprise growth. You’ll set the incentive systems that shape how our sellers focus, partner, and grow with customers. On a typical week, you’ll work with senior GTM leaders — including the Head of Sales and geo leaders — to translate business priorities into clear, accurate, scalable comp programs. What You'll Achieve: By your 90th day, map the current GTM Comp operating model and publish a roadmap for evolving the function as GTM grows. Introduce AI quick wins that improve the quality of work: triage inbound questions, help reps estimate payouts, flag discrepancies across systems, and automate reminders tied to the comp calendar. Build a planning-cycle framework that makes design inputs, trade-offs, decision rights, and timelines clear across GTM, Finance, and Commercial Operations. Provide board-level updates, including clear reporting on plan health, payout accuracy, systems quality

Perplexity is looking for an experienced Billing Operations Manager to join our Finance and Accounting team as we scale our enterprise business. You will own the enterprise billing lifecycle, translating complex commercial agreements into accurate, timely invoices and building the processes and controls that support our growth. This is a hands-on role working closely with Deal Desk, Enterprise Sales, Legal, and Customer Success. The ideal candidate combines strong billing and systems expertise with sound judgement, a customer-focused approach, and the ability to bring structure to a fast-moving environment. Responsibilities Enterprise and reseller billing: Own enterprise billing operations from customer and subscription setup through recurring invoicing, renewals, amendments, and cancellations, ensuring accurate and timely billing in accordance with executed agreements. Contract review: Partner with Enterprise Sales and Deal Desk to review nonstandard billing terms before contracts are signed, assess operational feasibility, and route exceptions for approval. Complex billing arrangements: Translate approved pricing and contractual terms into billing configurations and schedules, including seat changes, tiered discounting, prorations, co-terminations, prepaid credits, and usage billed in arrears. Billing inquiries and disputes: Serve as the primary point of contact for enterprise billing questions from customers and internal teams. Investigate discrepancies, coordinate approved credits and rebills, and address underlying causes to prevent recurring issues. Reconciliations and close support: Reconcile contract, subscription, and usage data to billing output and investigate any billing discrepancies. Support month-end close and audits through billing completeness checks, reconciliations, and supporting documentation. Integration management: Identifying and resolving any billing system integration failures. Customer Success and renewal support: Partner with Customer Suc