Role Overview

Datadog, the leading cloud monitoring and security platform, is seeking a Strategic Account Executive to drive new business with our largest Fortune 1000 customers. This remote role in Canada focuses on uncovering pain points in cloud migrations and operations at scale, delivering tailored Datadog observability solutions. Join a high-growth SaaS leader (NASDAQ: DDOG) where you'll prospect into enterprise accounts, build pipeline independently, and close deals averaging $100k+. With a hybrid workplace model, enjoy work-life harmony while targeting strategic prospects in cloud-native environments.

Perfect for seasoned sellers passionate about DevOps, observability, and infrastructure monitoring, this position offers uncapped earning potential and career acceleration in a collaborative, engineer-built culture.

Key Responsibilities at Datadog

• Prospect aggressively into Fortune 1000 companies, running efficient sales processes from discovery to close.
• Build and own territory relationship maps, nurturing existing contacts and targeting aspirational decision-makers.
• Deep-dive into customer businesses, identifying cloud operation pain points and migration challenges.
• Negotiate complex deals with large enterprises, emphasizing Datadog's ROI and value over pricing.
• Expand within assigned territory, managing renewals while growing account depth and breadth.
• Solve challenges resourcefully, navigating objections in complex sales cycles.
• Drive closures intuitively, securing customer validation through pilots and proofs-of-concept.
• Uncover business drivers for every opportunity, ensuring alignment with strategic priorities.
• Maintain forecasting excellence, delivering accurate pipeline visibility to leadership.
• Travel as needed to client sites across Canada and regions to build relationships.

Qualifications & Requirements

• 5+ years closing enterprise deals, blending mid-market and Fortune 1000 experience.
• Track record exceeding $1M+ quotas with $100k+ average deal sizes.
• Proven self-sourcing pipeline methodology in SaaS/IT infrastructure sales.
• Experience at innovative tech firms, ideally in observability, monitoring, or cloud.
• Success winning new logos at large enterprises; comfortable with travel.
• Intuitive sales acumen for complex, value-based negotiations.

Datadog welcomes passionate technologists—even if you don't match every qualification perfectly. Grow with us in cloud monitoring careers.

Salary & Benefits

Earn competitively in this Strategic Account Executive role at Datadog, with base salaries from $140,000-$200,000 USD plus uncapped commissions pushing OTE to $280,000+. Benefits include:

• Competitive equity: RSUs for new hires + ESPP.
• Family health insurance: Comprehensive medical, dental, vision coverage.
• Professional development: MEDDIC training, product certification paths.
• Retirement match and financial wellness programs.
• Pet insurance and adoption support.
• Mentorship programs with buddies and intra-team networking.
• Hybrid flexibility and commuter benefits where applicable.
• Inclusive culture: Join Community Guilds for ERGs and events.

Benefits tailored to Canadian employment standards.

Why Join Datadog?

Datadog powers digital transformation for global enterprises with our unified observability platform—monitoring infrastructure, applications, logs, security, and more. We're profitable, growing, and engineer-first, used by organizations across industries for cloud migration success.

Thrive in a people-first community that champions diversity, innovation, and excellence. Break silos, solve cloud complexity, and celebrate wins. Explore #DatadogLife on Instagram, LinkedIn, and our Learning Center. As a Strategic Account Executive, you'll shape customer success in DevOps and observability while accelerating your career.

How to Apply

Ready to close strategic deals with Datadog? Apply now for this remote Canada opportunity. Submit your resume highlighting enterprise sales wins, SaaS experience, and quota attainment. We'll review passionate applicants eager to sell cloud monitoring solutions. Equal opportunity employer—join the pack today!