Skip to content
DatadogDatadog

Staff Forward Deployed Engineer, Feature Flags

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.

About the job

Responsibilities

  • Serve as the hands-on technical partner for strategic customers implementing Datadog Feature Flags, from pre-sales validation through post-sales delivery.
  • Consult on flag architecture and implementation for complex, multi-service, multi-platform, high-scale environments.
  • Build prototype flag implementations in customer codebases to prove value and reduce technical risk.
  • Implement flags across server-side, client-side, edge, mobile, streaming, and real-time deployment modes.
  • Drive full flag migrations, including legacy-system cutovers, with minimal customer engineering burden.
  • Identify implementation patterns and share them with Product and Engineering to improve the platform and tooling.
  • Collaborate with Engineering on technical edge cases, product gaps, and implementation tools.
  • Partner with Sales and Solutions to accelerate deal cycles by removing technical risk.

Requirements

  • 5 years of professional software engineering experience.
  • Hands-on coding ability across the technology stack used by customers.
  • Experience with feature flagging, experimentation, or configuration-management systems.
  • Ability to quickly work in unfamiliar codebases, languages, and frameworks.
  • Experience shipping production code and supporting large-scale migrations.
  • Customer-facing experience or strong motivation to develop it.
  • Ability to explain complex technical tradeoffs to engineering and non-engineering stakeholders.
  • Comfortable operating with ambiguity and moving between architecture discussions and implementation.

Nice-to-haves

  • Forward-deployed, consulting, or professional-services engineering experience.
  • Startup or fast-scaling company experience with end-to-end ownership of ambiguous problems.

Compensation and Benefits

  • Salary: $244,000–$305,000 USD per year.
  • Competitive benefits package, RSUs, employee stock purchase plan, healthcare, dental, parental planning, mental health benefits, 401(k) plan and match, paid time off, fitness reimbursements, career development, onboarding, mentoring, and buddy programs.
  • Benefits may vary based on country of employment and employment type.

Skills

Feature Flags, Experimentation, Configuration Management, Software Engineering, Customer Codebases, Architecture Consulting, Server-Side Development, Client-Side Development, Mobile Development, Streaming, Real-Time Systems, System Migrations, Production Coding, Datadog

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.

OpenAI

OpenAI

San Francisco, CA

Field CTO
$302k+/yrHybrid15+ YOESolutions Architecture

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.