Role Overview

Datadog's Enterprise Sales Executive role represents a prime opportunity for seasoned sales professionals to drive revenue growth with the world's leading cloud monitoring and observability platform. Targeting Canada's largest enterprises, you'll uncover pain points in cloud migrations and operations at scale, positioning Datadog's comprehensive solutions to deliver immediate value. This remote position across Canada combines strategic territory management with high-impact deal closing, offering uncapped earning potential in a hybrid work environment that values work-life harmony.

At Datadog, Enterprise Sales Executives engage Fortune 1000 companies facing complex cloud challenges. You'll prospect strategically, build deep customer relationships, and close multi-hundred-thousand-dollar deals by demonstrating clear ROI through Datadog's industry-leading observability, monitoring, and security capabilities. With regular travel to key client sites, this role demands resilience, intuition, and proven enterprise sales success.

Key Responsibilities at Datadog

• Prospect aggressively into large Fortune 1000 companies while maintaining an efficient, high-velocity sales process optimized for enterprise deals.
• Build and own comprehensive relationship maps across your Canada territory, nurturing existing contacts while targeting aspirational decision-makers.
• Develop deep business comprehension of customer challenges in cloud operations, migrations, and observability to tailor Datadog solutions perfectly.
• Negotiate complex deals with favorable pricing and terms by articulating compelling value propositions and ROI metrics.
• Expand territory penetration by managing customer expectations while growing reach and depth within assigned accounts.
• Demonstrate resourcefulness in overcoming sales obstacles that require creative, non-traditional solutions.
• Maintain intuitive closing instincts to identify critical steps needed for customer validation and signature.
• Drive robust opportunity qualification by uncovering all key business drivers behind potential deals.
• Deliver forecasting excellence with high accuracy and consistency to support Datadog's continued growth trajectory.

Qualifications & Requirements

To succeed as a Datadog Enterprise Sales Executive in Canada, candidates must bring proven enterprise sales firepower:

• 3+ years of hands-on closing experience in field sales targeting mid-market or enterprise accounts.
• Demonstrated history of meeting/exceeding $1M+ annual quotas with average deal sizes exceeding $100k.
• Proven, repeatable methodology for independent prospecting and pipeline generation.
• Direct experience at innovative SaaS or IT infrastructure companies, with preference for observability/cloud monitoring domains.
• Established success selling into Fortune 1000 enterprises, including winning new logos against entrenched competition.
• Comfort with regular domestic and regional travel (car, train, air) to client sites as business demands.

Datadog celebrates diverse backgrounds and encourages passionate technologists to apply even if you don't match every qualification perfectly. Our people-first culture prioritizes growth and development.

Salary & Benefits

Datadog offers competitive total compensation for Enterprise Sales Executives, including base salary, uncapped commissions, and performance-driven accelerators. Additional perks create a comprehensive package:

• High-income potential tied directly to your sales performance and deal closure success.
• Equity ownership through new hire RSUs and ESPP participation.
• World-class sales training in MEDDIC methodology and Command of the Message techniques.
• Professional development programs, product deep-dives, and clear career pathing.
• Mentorship ecosystem with intra-departmental buddies and networking opportunities.
• Comprehensive health benefits including family coverage, retirement matching, and unique pet insurance/adoption support.
• Inclusive culture with Community Guilds fostering belonging and collaboration.

Benefits may vary by Canadian province and employment terms.

Why Join Datadog?

Datadog (NASDAQ: DDOG) stands at the forefront of cloud observability, powering digital transformation for enterprises worldwide. Our platform breaks down silos, enabling seamless monitoring of entire technology stacks—from infrastructure to applications and security. Join a profitable growth company built by engineers for engineers, where innovation meets execution.

Experience #DatadogLife: collaborative teams, smart risk-taking, and continuous celebration of wins. With hybrid flexibility, professional growth opportunities, and a commitment to diversity, Datadog empowers you to thrive. Follow us on Instagram, LinkedIn, and Datadog Learning Center.

How to Apply

Ready to accelerate your sales career with Datadog's cloud monitoring leadership? Apply now for this remote Enterprise Sales Executive role in Canada. Submit your resume highlighting quota attainment, deal sizes, and Fortune 1000 wins. Datadog provides equal opportunity regardless of background—join our pack today and help enterprises conquer cloud complexity.