Engineering Manager, Order Systems
WFA Digital Insight
As the remote job market shifts towards specialized technical roles, demand for skilled engineering managers has surged. With a 25% increase in AI-related job postings in the last year, OpenAI stands out as a pioneer in the field. This role is particularly interesting for those with experience in revenue platforms, complex commerce systems, and a passion for operational excellence. Before applying, candidates should be aware of the need for strong leadership, systems design, and data modeling skills, as well as the ability to drive clarity in ambiguous problem spaces.
Job Description
About the Role
The Engineering Manager, Order Systems position at OpenAI is a critical role that involves leading a team of engineers to build and operate workflows that power quoting, tracking, and fulfillment for the company's products. This role is part of the Financial Engineering team within Applied Engineering and collaborates closely with the GTM and Finance teams to ensure effective monetization of OpenAI's products. The team's primary focus is on developing and maintaining the billing stack to accommodate the company's evolving internal requirements.As a key member of the Financial Engineering team, the Engineering Manager will play a vital role in driving the technical direction and strategy for order management automation. This includes owning the architecture and roadmap for order data flows into downstream systems, such as internal provisioning services, billing and invoicing services, and revenue workflows. The role also involves building and operating resilient workflows and services that automate entitlements, provisioning, usage controls, SKU attribution, invoice generation and delivery, and revenue recognition.
The Engineering Manager will work closely with cross-functional teams, including Sales Operations, Finance, Accounting, Support, Product, Security, and Compliance, to translate requirements into resilient and auditable workflows. This role requires strong leadership, technical expertise, and the ability to drive clarity in ambiguous problem spaces.
What You Will Do
- Lead and grow a team of engineers responsible for order management automation, focusing on reliability, correctness, and smooth customer onboarding
- Own the architecture and roadmap for order data flows into downstream systems, such as internal provisioning services, billing and invoicing services, and revenue workflows
- Build and operate resilient workflows and services that automate entitlements, provisioning, usage controls, SKU attribution, invoice generation and delivery, and revenue recognition
- Improve accuracy and timeliness of provisioning, billing, and invoicing, reducing manual intervention and operational load through automation, validation, and reconciliations
- Establish strong operational practices, including observability, alerting, runbooks, and on-call, to ensure systems remain healthy without constant human oversight
- Partner deeply with cross-functional teams to translate requirements into resilient and auditable workflows
- Drive clarity across ambiguous problem spaces and evolving product offerings, creating frameworks and abstractions that scale as OpenAI's commercial footprint expands
- Set high engineering standards through technical direction, design reviews, mentoring, and fostering a culture of ownership and continuous improvement
- Bring strong leadership, teaching, and leveling up engineers, recruiting and retaining talent, managing stakeholders, and scoping work to balance customer needs with realistic deliverables
- Collaborate with the GTM team to develop and implement pricing strategies and revenue models
- Work with the Finance team to ensure accurate and timely financial reporting and compliance
What We Are Looking For
- 7+ years of professional software engineering experience, including 3+ years leading engineers or managing teams
- Experience integrating revenue platforms, such as CPQ, billing, invoicing, and revenue recognition systems
- Strong systems design, data modeling, and building reliable distributed services and workflows
- Experience in domains where correctness, auditability, and reconciliation are essential, such as payments, ERP/finance systems, and invoicing/revenue recognition
- Ability to lead or effectively partner on customer-facing billing experiences with a focus on clarity, accessibility, and trust
- Strong leadership, communication, and collaboration skills, with the ability to build trust and lead with context rather than control
- Experience with large-scale SaaS billing or enterprise account provisioning, usage-based and/or seat-based pricing, and invoice generation at scale
- Familiarity with finance and revenue operations concepts, such as proration, credits/adjustments, and revenue schedules
- Exposure to common CRM/ERP and payment ecosystems, such as CPQ, invoicing, collections, and payment processors
Nice to Have
- Experience with Adjust, Excel, and other relevant tools and technologies
- Familiarity with machine learning and AI concepts, and their applications in revenue management and forecasting
- Experience with cloud-based infrastructure and services, such as AWS or Google Cloud
- Knowledge of security and compliance frameworks, such as SOC 2 or ISO 27001
- Experience with agile development methodologies and version control systems, such as Git
Benefits and Perks
- Competitive salary and equity package
- Comprehensive health, dental, and vision insurance
- Flexible PTO and paid holidays
- Remote work stipend and equipment allowance
- Opportunities for professional growth and development, including training and education programs
- Access to cutting-edge technologies and tools
- Collaborative and dynamic work environment
- Recognition and reward programs for outstanding performance
- Employee wellness programs, including mental health support and employee assistance programs
How to Stand Out
- Tip: Highlight your experience with revenue platforms, such as CPQ, billing, and invoicing systems, and be prepared to discuss your approach to integrating these systems with other tools and technologies.
- Tip: Showcase your ability to lead and manage teams, including experience with agile development methodologies and version control systems, such as Git.
- Tip: Emphasize your strong systems design, data modeling, and building reliable distributed services and workflows skills, and be prepared to discuss your approach to building scalable and resilient systems.
- Tip: Be prepared to discuss your experience with large-scale SaaS billing or enterprise account provisioning, usage-based and/or seat-based pricing, and invoice generation at scale.
- Tip: Highlight your familiarity with finance and revenue operations concepts, such as proration, credits/adjustments, and revenue schedules, and be prepared to discuss your approach to financial reporting and compliance.
- Tip: Research OpenAI's products and services, and be prepared to discuss your understanding of the company's mission and values, as well as your experience with machine learning and AI concepts, and their applications in revenue management and forecasting.
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