Director, Enterprise Pre-Sales Engineering - AI & Cloud

Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across their entire technology stack to manage complexity at scale.

As Director, Enterprise Sales Engineering, you will serve as a strategic executive leader across the North America region, managing a high-performing organization of frontline Sales Engineering (SE) Managers and individual contributors. Acting as a force multiplier for Datadog’s go-to-market engine, you will partner closely with senior Sales leadership to shape regional multi-quarter strategies, optimize capacity planning, and drive high-stakes deal execution. You will establish repeatable technical sales methodologies that illustrate the measurable business value of Datadog’s observability and cloud security solutions—especially within environments transformed by Agentic AI, public cloud, Kubernetes, and modern APM/tracing stacks.

Key Responsibilities

• Regional Executive Leadership & Field Execution: Provide senior-level stakeholder alignment, executive presence, and technical credibility on high-impact enterprise sales opportunities across North America.
• Leadership Development & Management: Lead, coach, and scale a team of frontline Sales Engineering Managers—fostering technical excellence, driving career progression, and building a high-trust, inclusive team culture.
• GTM Strategy & Sales Partnership: Partner with senior Sales Vice Presidents on regional GTM strategy, annual headcount planning, and revenue forecasting 2–3 quarters ahead of execution.
• Repeatable Pre-Sales Methodology: Operationalize scalable evaluation frameworks (utilizing methodologies like MEDDICC / Command of the Message) to accelerate deal velocity and prove value around Agentic AI and cloud observability.
• Regional Operational Excellence: Manage resource allocation, SE utilization rates, KPI tracking, productivity metrics, and skills enablement programs across the region.
• Cross-Functional Executive Collaboration: Bridge regional field insights with executive stakeholders across Product Management, Marketing, Support, and Enablement to shape the core product roadmap and customer experience.
• Talent Acquisition & Enablement: Lead regional hiring strategies to attract, onboard, and retain top-tier technical sales leaders and enterprise solutions engineers.
• Market Intelligence & AI Scaling: Monitor competitive shifts, cloud security trends, and scale the adoption of AI productivity tools within the Sales Engineering organization.

Requirements

Executive Leadership & Technical Depth

• 5+ years of experience leading frontline Sales Engineering / Solutions Engineering managers in a customer-facing technical organization.
• 10+ years of total experience in Sales Engineering, Solutions Architecture, or enterprise technical customer-facing roles.
• Enterprise Domain Expertise: Deep background in public cloud ecosystems (AWS, Azure, GCP), Kubernetes, APM/tracing, cloud security, microservices, and observability platforms.
• Senior Stakeholder Alignment: Proven success engaging C-level executives, SRE directors, DevOps leads, and Chief Information Security Officers (CISOs).
• Sales Methodology Mastery: Deep expertise in enterprise sales frameworks (MEDDICC, MEDDPICC, Command of the Message).
• Cross-Functional & Partner Influence: Ability to navigate joint selling motions alongside major hyperscaler partners and global channel organizations.
• AI Tooling Proficiency: Demonstrated track record of leveraging and scaling modern AI tools within pre-sales and team operations.
• Strategic & Operational Balance: Capability to manage multi-quarter strategic planning while maintaining oversight of day-to-day SE execution.

Preferred Qualifications

• Experience scaling pre-sales organizations through rapid hyper-growth and IPO/public market stages.
• Industry reputation as a thought leader in observability, AIOps, or cloud-native security architecture.
• Demonstrated experience delivering technical keynote presentations and leading executive briefing sessions.

Total Rewards & Benefits

• Compensation & Equity: Base salary range of $180,000 – $240,000 USD + variable incentive compensation + Restricted Stock Units (RSUs) + Employee Stock Purchase Plan (ESPP) discount.
• Healthcare & Family Support: Comprehensive health, dental, and vision insurance coverage, parental planning support, and mental health stipends.
• Retirement & Financial: 401(k) plan with company match, fitness reimbursements, and generous paid time off.
• Culture & Growth: Best-in-breed onboarding, cross-departmental mentor and buddy programs, continuous product training, and access to internal Community Guilds.