Skip to content
OpenAIOpenAI

Field CTO

Leads strategic technical pursuits for enterprise customers, advising on architecture, AI deployments, and complex sales cycles while translating field insights into product and go-to-market strategy. Requires 15+ years of technical leadership experience, enterprise architecture expertise, and strong executive communication.

About the job

Responsibilities

  • Partner with Sales, Product, and Technical Success teams on complex, high-value enterprise deals as a technical and strategic advisor.
  • Translate customer business needs into scalable technical solutions and architectures.
  • Engage CTO-, CIO-, and VP-level stakeholders to align on vision, roadmap, and adoption.
  • Lead technical strategy discussions across discovery, solution design, and executive presentations.
  • Guide customers on deploying and scaling AI-driven solutions in production.
  • Provide architectural oversight for LLM applications, integrations, data pipelines, and security.
  • Bring structured customer insights to Product and Engineering to inform roadmap and prioritization.
  • Identify deployment gaps, opportunities, and emerging patterns.
  • Shape go-to-market strategies, reference architectures, frameworks, and playbooks.
  • Represent the company through customer engagements, industry events, and thought leadership.

Requirements

  • 15+ years of experience in technical leadership roles.
  • Strong background in enterprise architecture, cloud platforms, and modern software systems.
  • Experience supporting enterprise sales cycles or working closely with go-to-market teams.
  • Ability to translate complex technical concepts into clear business value for non-technical stakeholders.
  • Strong problem-solving skills with ownership and bias for action.
  • Excellent communication and executive presence.
  • Ability to influence without authority across cross-functional teams.

Nice to Have

  • Exposure to AI/ML systems, especially large language models and applied AI use cases.

Skills

Enterprise Architecture, Cloud Platforms, Software Systems, Artificial Intelligence, Machine Learning, LLMs, Data Pipelines, Security, Solutions Architecture, Technical Strategy

Datadog

Datadog

New York, NY

Staff Forward Deployed Engineer, Feature Flags
$244k+/yrHybrid7+ YOESolutions Architecture

Staff Forward Deployed Engineer who partners with strategic customers to architect, prototype, implement, and migrate feature-flag systems across complex production environments. The role requires strong software engineering fundamentals, customer-facing communication, and the ability to work across unfamiliar stacks.

OpenAI

OpenAI

San Francisco, CA

IT Software Architect, SaaS Enablement and Governance
$230k+/yrHybrid10+ YOESolutions Architecture

Leads enterprise software, SaaS, integration, identity, data, and agent-enabled architecture across Corporate IT. The role requires 10+ years of enterprise or IT architecture experience and strong expertise in governance, security, vendor strategy, and cross-functional enablement.

Upside

Upside

New York, NY

Staff Forward Deployed Engineer, GTM Platform
$214k+/yrHybrid8+ YOESolutions Architecture

Build and own a zero-to-one AI-native platform for internal go-to-market teams, embedding with revenue operations to transform workflows and deliver measurable business outcomes. The role requires staff-level engineering depth, production LLM experience, and strong architectural judgment.

Fivetran

Fivetran

Georgia

Staff Solutions Architect
$198k+/yrRemote7+ YOESolutions Architecture

Leads technical solution design, demonstrations, and proof-of-value engagements for enterprise customers in partnership with sales. Requires 7+ years of enterprise solutions engineering experience, strong data-platform expertise, and willingness to travel at least 30%.

Kong

Kong

United States

Senior Staff Forward Deployed Engineer
$192k+/yrRemote8+ YOESolutions Architecture

Build and deploy Kong API and AI connectivity solutions for enterprise customers, leading migrations, automation, integrations, and production implementations across cloud-native environments. Requires 8+ years of engineering experience, strong Kubernetes and cloud expertise, and customer-facing technical leadership.