Staff Forward Deployed Engineer, Feature Flags

As a Forward Deployed Engineer on the Feature Flags team, you'll partner directly with customers to accelerate their feature flag implementations — from initial architecture consulting through prototype builds to full-scale migrations. This role is for someone who wants to write code with customers, not just advise them. You'll work hands-on inside customer codebases to unblock complex, high-stakes deployments, directly influencing deal velocity and customer success. Working closely with Sales, Solutions, and Engineering, you'll be the technical force that turns a signed contract into a live, adopted implementation.

What You'll Do:

• Serve as the hands-on technical partner for strategic customers implementing Datadog Feature Flags, from pre-sales technical validation through post-sales delivery
• Consult on flag architecture and implementation approach for complex environments — multi-service, multi-platform, high-scale deployments
• Build prototype flag implementations directly in customer codebases to prove value and de-risk technical decisions early in the sales cycle
• Implement flags across diverse and advanced deployment modes (server-side, client-side, edge, mobile, streaming/real-time) tailored to each customer's stack
• Drive full flag migrations to completion — including legacy system cutover — efficiently and with minimal customer engineering burden
• Identify patterns across customer implementations and feed them back to Product and Engineering to improve the core product and reduce future implementation time
• Collaborate closely with Engineering on technical edge cases, product gaps, and implementation tooling
• Partner with Sales and Solutions to accelerate deal cycles by removing technical risk and uncertainty

Who You Are:

• 5 years of professional software engineering experience, with hands-on coding ability across the stack you're deployed into
• Experience with feature flagging, experimentation, or config management systems (internal or vendor)
• Comfortable dropping into unfamiliar codebases, languages, and frameworks quickly — no specific stack required, but strong fundamentals and fast ramp-up
• Experience shipping production code, not just prototypes — you understand the difference between a demo and something that survives a migration
• Customer-facing experience, or strong motivation to build it — comfortable being in the room with customer engineers, understanding their constraints, and adapting your approach
• Skilled at simplifying complex technical tradeoffs for both engineering and non-engineering stakeholders
• Motivated by outcomes — deal velocity, successful migrations, and customer trust — not just elegant code
• Comfortable operating with ambiguity, moving between architecture conversations and hands-on implementation in the same week

Bonus Points:

• Experience in a forward-deployed, consulting, or professional services engineering role
• Exposure to large-scale system migrations
• Prior work in a startup or fast-scaling environment where you had to own ambiguous problems end-to-end

About the Team

This team built Eppo — the market-leading experimentation and feature flagging platform trusted by companies like Coinbase, Perplexity, and DraftKings — and joined Datadog through its acquisition. Feature Flags sits at the center of that suite that includes experimentation, product analytics, session replay, RUM, and synthetics. As a Forward Deployed Engineer, you'll work directly inside customer codebases to make that loop real — turning flag architecture decisions into shipped, adopted implementations, and helping our most strategic customers build flag-driven development as a core engineering capability.

Working Model:

This role is based in New York City and works closely with Engineering on a regular basis.

Benefits and Growth:

• Generous and competitive benefits package
• New hire stock equity (RSUs) and employee stock purchase plan
• Continuous career development and pathing opportunities
• Employee-focused best in class onboarding
• Internal mentor and cross-departmental buddy program
• Friendly and inclusive workplace culture

Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog.

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