About the RoleAs Enterprise Sales Manager, Digital Natives, you will build and lead a team of Account Directors serving OpenAI's enterprise Digital Native customers: scaled technology companies, AI-native businesses, product-led platforms, and digitally native enterprises adopting AI across core products, operations, and customer experiences.
This is an enterprise leadership role in a segment that moves quickly but buys, deploys, and governs AI at scale. You will coach senior sellers through complex technical and executive sales cycles, deepen founder and C-suite relationships, and build durable account strategies across API/platform, ChatGPT Enterprise, Codex, and emerging AI use cases.
You will help define the GTM strategy, operating model, and customer playbook for enterprise Digital Natives where product velocity, usage expansion, technical credibility, security posture, procurement rigor, and executive alignment all matter.
Key Responsibilities- Recruit, develop, and lead a high-performing team of Account Directors responsible for strategic enterprise Digital Native accounts, large revenue opportunities, consumption growth, and multi-product expansion.
- Set the GTM strategy for enterprise Digital Natives, including segmentation, account prioritization, territory design, executive engagement, expansion coverage, and usage growth.
- Coach sellers through complex, multi-threaded cycles involving founders, CEOs, CTOs, CPOs, CIOs, engineering leaders, product leaders, security, legal, procurement, finance, and business executives.
- Drive disciplined pipeline generation, forecast accuracy, deal inspection, consumption planning, expansion planning, and executive alignment across high-value accounts.
- Build an operating cadence for account planning, deal reviews, technical discovery, mutual action plans, customer adoption reviews, and structured 1:1s that raise team performance.
- Partner with Solutions Architecture, FDE, Technical Success, Product, Legal, Security, Finance, and Support to land and expand enterprise-grade AI deployments.
- Translate enterprise Digital Native customer needs into product and commercial feedback across APIs, ChatGPT Enterprise, Codex, governance, trust and safety, security, pricing, packaging, and deployment patterns.
- Help customers move from experimentation to production AI adoption across product experiences, developer workflows, customer support, employee productivity, workflow automation, and AI-native business models.
- Build a culture of accountability, customer empathy, low-ego collaboration, and operating rigor while preserving the speed and curiosity that make the Digital Natives motion effective.
What We're Looking For- A senior enterprise sales leader who has built and scaled teams serving strategic Digital Native, technology, SaaS, cloud, developer-platform, or AI-native customers.
- A technical GTM thinker who can connect customer strategy to OpenAI's platform, ChatGPT Enterprise, Codex, and emerging AI use cases.
- An executive-facing operator who can engage founders, CEOs, CTOs, CPOs, CIOs, AI leaders, product leaders, engineering leaders, and enterprise platform teams.
- A disciplined builder who can install enterprise-grade rigor in forecasting, account planning, deal inspection, and performance management without slowing customer pace.
- A talent-first leader who raises the bar for senior sellers through clear hiring standards, coaching, accountability, and low-ego leadership.
- A cross-functional partner who can turn customer signal into practical product, commercial, security, and deployment feedback.
Skills & ExperienceRequired- 15+ years of enterprise sales, GTM, or sales leadership experience, including leadership of teams selling to strategic Digital Native or technology accounts.
- Experience with complex enterprise buying motions involving technical, security, legal, procurement, finance, and executive stakeholders.
- Working fluency in APIs, platform technologies, ChatGPT Enterprise, AI/ML concepts, governance, enterprise architecture, and consumption-based commercial models.
- Demonstrated operating discipline across forecasting, pipeline quality, account prioritization, inspection, and performance management.
Preferred- Experience selling platform, cloud, infrastructure, developer, data, AI, workflow, or consumption-based solutions.
- Experience with scaled digital enterprises or late-stage technology companies moving from pilots to production AI adoption.
- Public company or other high-accountability operating experience.
Nice to Have- Exposure to marketplaces, fintech, consumer internet, modern SaaS, data/ML platforms, or AI-native applications.
- Experience helping a high-growth segment mature into enterprise-grade account strategy, governance, procurement, and expansion.
