Director OF Enterprise Sales

Director, Enterprise Sales Engineering - US East Boston, Massachusetts, USA; New York, New York, USA As a Director, Enterprise Sales Engineering, you will lead a team of frontline leaders, driving account strategy, deal execution, operational excellence, and team development across your region. This is a strategic leadership role with regional impact within North America. You will act as a force multiplier by owning team and region performance, shaping execution standards, and partnering closely with Sales leadership to influence go to market strategy, improve outcomes, and scale impact beyond individual deals. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Own in-field execution at a regional level by taking an executive presence role in strategic and high-impact opportunities and providing senior-level stakeholder alignment and technical credibility alongside your team. Develop and operationalize a repeatable formula and methodology that can scale across a large customer base, enabling Datadog to accelerate enterprise growth by illustrating to customers how Datadog’s observability and security solutions quickly, simply, and efficiently deliver measurable business outcomes especially in a world increasingly dominated by Agentic AI. Partner confidently with senior Sales leadership on regional strategy, multi-quarter planning, annual capacity planning, and forecast alignment operating 2-3 quarters ahead to anticipate resourcing needs and business priorities. Oversee consistent, high-quality delivery across technical sales cycles in the region, including evaluations, customer engagements, and deal progression. Lead, coach, and develop a team of Sales Engineering leaders, driving performance, engagement, and long-term career growth through regular feedback and structured development. Hire and onboard top talent across ICs and manager-level roles, building a high-performing team and accelerating customer adoption through structured onboarding and enablement. Manage regional operations including resource allocation, utilization, KPI tracking, productivity, and skills development to ensure effective coverage across the territory. Collaborate cross-functionally with Sales, Product, Marketing, Enablement, and Support at a senior level to align on regional strategy, GTM execution, and customer experience. Drive operational excellence across the region by improving processes, maintaining data quality, scaling evaluation frameworks, and contributing to initiatives that improve team effectiveness and business impact. Track competitive developments, market dynamics, and emerging technologies to ensure the team is equipped to position Datadog as a leader in cloud security. Who You Are: 5+ years of experience leading frontline SE leaders in a customer-facing technical organization with proven ability to manage team performance, develop team members, and scale high-performing teams. 10+ years of experience in Sales Engineering, Solutions Engineering, or a technical customer-facing role. Demonstrated success leading solution engineering teams with senior stakeholders across Product, SRE, DevOps, and Engineering teams. Is naturally proactive, constantly introducing new ideas and finding better and more efficient ways to help SEs deliver better outcomes for our customers. Ability to operate at both strategic and operational levels, balancing multi-quarter planning with day to day team execution and priorities. Proven ability to influence cross-functional teams and navigate complex joint selling motions, particularly with partners and channel organizations. Excellent communication and stakeholder management skills with both internal teams and customer executives. Expert storytelling capabilities, with a strong ability to explain complex security concepts into everyday language that both technical and business audiences can understand. Passion for building scalable processes and fostering a collaborative, inclusive team culture. Track record of driving technical sales success at scale. Exceptional leadership, coaching, and team-building capabilities, with experience scaling high-impact teams. Background in public cloud (AWS, Azure, GCP), Kubernetes, APM/tracing, security, developer experience, observability or adjacent SaaS technology. Deep understanding of sales methodologies such as MEDDICC, Command of Message (CoM), or similar frameworks. Demonstrated capability of utilizing AI tooling and scaling it. Willingness to travel as needed to support customer engagements or internal meetings. Benefits and Growth: Best-in-breed onboarding Intra-departmental mentor and buddy program for in-house networking New hire stock equity (RSUs) and employee stock purchase plan (ESPP) Continuous professional development, product training, and career pathing An inclusive company culture, able to join our Community Guilds and Inclusion Talks Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog. The reasonably estimated yearly salary for this role at Datadog is: $180,000 — $240,000 USD Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram , LinkedIn, and Datadog Learning Center. Equal Opportunity at Datadog: Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference. Datadog endeavors to make our Careers Page accessible to all users. 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