Role Overview

Join Datadog as a Senior Sales Engineer in Chicago, Illinois and become a key player in driving enterprise cloud monitoring and observability solutions. Datadog is the leading monitoring and security platform for cloud applications, helping DevOps teams, developers, and business leaders optimize performance across dynamic, high-scale infrastructure. As a Senior Sales Engineer, you'll provide technical expertise through compelling sales presentations, hands-on product demonstrations, and supporting technical evaluations (POVs). You'll partner closely with sales teams to qualify and close opportunities while influencing product roadmap based on real customer feedback from enterprises using Datadog observability.

This role is perfect for technical sales professionals passionate about cloud monitoring, DevOps, and modern observability stacks. With up to 45% travel to client sites in the Midwest region, you'll engage directly with Fortune 500 companies adopting Kubernetes, AWS, and multi-cloud environments. Even if you don't meet every qualification on day one, Datadog encourages passionate technologists to apply and grow within our inclusive culture.

Key Responsibilities at Datadog

As a Senior Sales Engineer at Datadog, your impact will be immediate and measurable. Here's what you'll do daily:

• Partner with the Sales team to articulate the overall Datadog value proposition, vision, and strategy to customers adopting cloud-native observability.
• Own technical engagement with customers during the trial phase, communicating value based on activities and resolving issues to successful conclusion.
• Technically close complex opportunities through advanced competitive knowledge of tools like New Relic, Splunk, and Dynatrace, leveraging your technical skill and credibility.
• Deliver engaging product and technical briefings/presentations to potential clients, showcasing Datadog APM, infrastructure monitoring, and security features.
• Maintain accurate notes and feedback in CRM regarding customer input on both wins and losses to drive continuous improvement.
• Proactively engage and communicate with customers and Datadog business/technical teams regarding product feedback and competitive landscape insights.
• Support technical evaluations (POVs) by building custom dashboards, integrations with Python, Terraform, and Docker environments.
• Help qualify opportunities with customers and partners while providing voice-of-customer input to prioritize features in Datadog's observability platform.
• Educate customers on observability risks meaningful to their business, building and executing comprehensive evaluation plans.

Qualifications & Requirements

Datadog seeks proven performers with hands-on experience in technical sales and cloud technologies. Key qualifications include:

• 3+ years in Sales Engineering or DevOps Engineering roles, ideally in SaaS or cloud monitoring space.
• Strong programming/scripting experience with Java, Python, Ruby, Go, Node.js, PHP, .NET – essential for custom integrations and demos.
• Exceptional written and oral communication skills to translate complex technical advantages into compelling business value propositions.
• Passion for educating customers on observability risks like downtime, performance bottlenecks, and security vulnerabilities in cloud apps.
• Ability to travel up to 45% (auto, train, air) and sit for extended periods during client engagements.
• Advanced knowledge of competitive landscape in cloud observability, APM, and infrastructure monitoring.

Datadog values diversity – if you're excited about Datadog careers and want to level up your skills in a high-growth environment, apply today!

Salary & Benefits

Datadog offers competitive compensation for Senior Sales Engineer roles in Chicago: $149,000 - $198,000 USD base salary, plus variable compensation, equity, and comprehensive benefits. Total on-target earnings (OTE) can exceed $250K+ for top performers.

Standout perks include:

• New hire stock equity (RSUs) and ESPP for long-term wealth building.
• Best-in-class healthcare, dental, parental planning, and mental health benefits covering families.
• 401(k) with generous company match.
• Fitness reimbursements, commuter benefits, and unlimited PTO.
• Professional development with product training, certifications in AWS, Kubernetes, and observability tools.

Why Join Datadog?

Datadog isn't just a job – it's a launchpad for your career in cloud monitoring and observability. Work with cutting-edge technologies powering the world's largest cloud applications. Our Chicago team collaborates with global engineering, product, and sales orgs. Enjoy an inclusive culture with Community Guilds, Inclusion Talks, and intra-departmental mentoring. Continuous growth through career pathing, skill-building workshops, and exposure to enterprise customers transforming with Datadog DevOps solutions. Best-in-breed onboarding ensures you're productive from day one.

Datadog's platform unifies metrics, traces, and logs across AWS, Azure, GCP, Kubernetes, and serverless – join the team revolutionizing how teams observe modern infrastructure.

How to Apply

Ready to accelerate your career as a Senior Sales Engineer at Datadog? Click 'Apply Now' to submit your resume. Highlight your Datadog, Python, or DevOps experience. We'll review applications quickly – top candidates interview within a week. Datadog is an equal opportunity employer committed to diversity. Chicago Sales Engineer jobs fill fast – apply today!