Technical Escalations Engineer 2 (Logs) - US-East

Cargurus

Who we are At CarGurus (NASDAQ: CARG), our mission is to give people the power to reach their destination. We started as a small team of developers determined to bring trust and transparency to car shopping. Since then, our history of innovation and go-to-market acceleration has driven industry-leading growth. In fact, we’re the largest and fastest-growing automotive marketplace, and we’ve been profitable for over 15 years. What we do The market is evolving, and we are too, moving the entire automotive journey online and guiding our customers through every step. That includes everything from the sale of an old car to the financing, purchase, and delivery of a new one. Today, tens of millions of consumers visit CarGurus.com each month, and ~30,000 dealerships use our products. But they're not the only ones who love CarGurus—our employees do, too. We have a people-first culture that fosters kindness, collaboration, and innovation, and empowers our Gurus with tools to fuel their career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives. Come join us for the ride! Role overview The Principal IT Systems Administrator is the most senior individual contributor on the IT Systems team, setting technical direction for core platforms, endpoints, networks, and security within IT Operations. This role drives reliability, scalability, and automation. You will lead complex initiatives, serve as a top escalation point, and partner across the business to ensure infrastructure and endpoints enable productivity while meeting security and compliance needs. What you'll do * System Configuration & Administration: Design and implement complex configurations for core IT platforms (identity, collaboration, infrastructure, SaaS). Establish configuration management, lead performance/reliability improvements, and automate repetitive tasks. * Workspace & Endpoint Management: Design enterprise-wide endpoint strategies (macOS, Windows, mobile). Develop and enforce security policies, automate software/OS deployments via MDM/EMM, and own compliance reporting. * Network & Infrastructure: Design and implement complex network configurations (LAN/WAN/Wi-Fi/VPN/voice) for scalability and security. Maintain monitoring, automate network management, and lead infrastructure projects (e.g., migrations, new site buildouts). * Security Engineering & Operations: Define and drive security strategies within IT Systems (identity, access, endpoints, networks). Integrate security tools (SSO/MFA, EDR, DLP), enforce access policies, and act as a technical lead during critical security incidents. * Incident Management & Reliability: Define and implement incident response strategies, lead Post-Incident Reviews (PIRs) to drive corrective action, develop runbooks, and oversee on-call rotations. * Documentation & Knowledge Management: Define documentation standards (architecture, SOPs, runbooks) and ensure knowledge bases are accurate, comprehensive, and easily discoverable. What you'll bring * Extensive experience (typically 8+ years) in IT systems engineering/administration, with significant time in senior/lead roles on enterprise-scale environments. * Deep expertise in: Core IT systems (identity, collaboration, directory), Endpoint management (MDM/EMM, lifecycle), Network infrastructure (switching, routing, VPN), and Security controls (EDR, SSO/MFA). * Demonstrated ability to design complex configurations, lead large cross-functional projects, and influence architectural decisions. * Strong automation mindset and proficiency with scripting/infrastructure-as-code (Python, PowerShell, Terraform). * Proven track record leading major incidents and PIRs. * Excellent cross-functional collaboration and communication skills, comfortable engaging all levels. * Experience in environments with security, regulatory, or audit requirements (SOC 2, SOX). * A bias toward ownership, documentation, and mentorship. Nice to have: Experience in a high-growth SaaS or technology company, familiarity with CarGurus tools (Okta, Google Workspace/M365, Jamf, Intune), and experience partnering with Security Engineering and GRC.   The displayed range represents the expected annual base salary / On-Target Earnings (OTE) for this position. On-Target Earnings (OTE) is inclusive of base salary and on-target commission earnings, which applies exclusively to sales roles. Individual pay within this range is determined by work location and other factors such as job-related skills, experience, and relevant education or training. This annual base salary forms part of a comprehensive Total Rewards Package. In addition to benefits, this role may qualify for discretionary bonuses/incentives and Restricted Stock Units (RSUs). Position Pay Range $113,000—$142,000 USD Working at CarGurus We reward our Gurus’ curiosity and passion with best-in-class benefits and compensation, including equity for all employees, both when they start and as they continue to grow with us. Our career development and corporate giving programs, as well as our employee resource groups (ERGs) and communities, help people build connections while making an impact in personally meaningful ways. A flexible hybrid model and robust time off policies encourage work-life balance and individual well-being. Thoughtful perks like daily free lunch, a new car discount, meditation and fitness apps, commuting cost coverage, and more help our people create space for what matters most in their personal and professional lives. CarGurus may require in-person interviews as part of our hiring process, particularly for positions based in our Boston and Dublin offices. Candidates selected for an in-person interview will be notified in advance. Please be aware that travel expenses are the responsibility of the candidate. We welcome all CarGurus strives to be a place to which people can bring the ultimate expression of themselves and their potential—starting with our hiring process. We do not discriminate based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation. We foster an inclusive environment that values people for their skills, experiences, and unique perspectives. That’s why we hope you’ll apply even if you don’t check every box listed in the job description. We also encourage you to tell your recruiter if you require accommodations to participate in our hiring process due to a disability so we can provide the appropriate support. We want to know what only you can bring to CarGurus. #LI-Hybrid

Datadog

We are Datadog's in-house product experts. The technical solutions team enables Datadog's worldwide growth by educating potential clients and ensuring that existing customers are happy and successful. A Technical Account Manager (TAM) will continue to provide hands-on technical services to our largest customers by supporting, adopting and providing guidance over the comprehensive suite of products and features available at Datadog. A TAM is held in high regard as an expert and trusted advisor for how IT Operations translates to business value. 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: * Advise on technical support and product adoption for customers in line with pre-sales, post-sales and the renewal processes * Analyze customer’s IT Operations environment on a regular basis and provide recommendations that will maximize Datadog’s value. * Be the customer’s advocate by knowing their goals and use cases then suggesting process changes, product adoption, configuration and additional features to meet their requirements * Participate and prepare for Monthly and Quarterly Business Reviews with customers * Collaborate with Datadog’s product management, engineering and technical services teams to help identify new features and products * Continuously evolve best practice to technical product adoption and customer success Who You Are: * Someone with a solid technical grounding and hands-on experience of IT Operations * Confident in your hands on experience AWS, Azure or GCP * Comfortable scripting languages like Python, Javascript, Ruby, Perl, Go, PHP, or Chef/Puppet etc. * Skilled in using CI/CD tools e.g. Jenkins, Gitlab etc. * Knowledgeable about Containerization tools e.g. Docker, Kubernetes or Rancher etc. * Able to sit up to 4 hours, traveling to and from client sites  * Able to travel via auto, train or air up to 30% of the time * Previous experience working as a TAM supporting mid-market and/or Enterprise customers in the cloud space * Experienced using Datadog and/or other cloud monitoring tools Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your skills, we encourage you to apply. Benefits and Growth: * Best-in-breed onboarding * Generous global benefits * 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.   #LI-Hybrid Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan. The reasonably estimated yearly salary for this role at Datadog is: $101,000—$147,000 USD ---------------------------------------------------------------------------------------------------------------------------------- About Datadog:  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. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. This form is for accommodation requests only and cannot be used to inquire about the status of applications.  Privacy and AI Guidelines: Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.

Datadog

The Product Solutions Architecture (PSA) team acts as a technical multiplier across Datadog. PSAs are domain experts who partner with Field teams on complex customer use cases across pre- and post-sales engagements and scale their impact by producing reusable collateral, including reference architectures, technical guides, and enablement assets. By feeding real-world customer insights back to Datadog Product teams, PSAs help influence product roadmaps while accelerating adoption, usage, and long-term customer success. The Digital Experience & Experimentation family of products includes Product Analytics, Feature Flags, Experimentation, and Session Replay and is a fast-growing segment at Datadog and addresses a distinct buyer, product managers, digital experience teams, and product engineers building and optimizing customer-facing applications. As a Product Solutions Architect, you will partner closely with Datadog customers and the Product team to design architectures, implement best practices, and drive adoption of this digital experience product family across customer environments. 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: * Serve as an in-house subject matter expert for the Datadog Product Analytics, Feature Flags, Experimentation, and Session Replay and related products. * Partner with field teams to offer guidance on architecture choices, SDK instrumentation, data collection, and best practices to large Enterprise customers as they adopt the product family. * Act as a trusted advisor to Product Management by delivering actionable feedback informed by real-world field experience. * Create high-impact technical collateral, including reference architectures, technical guides, cookbooks, and documentation to enable Field teams and the broader customer community. * Build world class training material, solutions briefs, blogs, and documentation to the wider Datadog field technical teams over the latest product features and capabilities. * Collaborate with other teams at Datadog including Marketing, Sales, Community, Documentation, and Evangelism to ensure the success of the Product Analytics product family. * Build proofs of concept and small-scale deployments to validate solutions and reproduce real-world customer environments. * Collaborate on defining the technical GTM motion for Feature Flags and Experimentation, including competitive positioning against competitors to enable Sales Engineers globally to run these conversations independently. Who You Are: * 5+ years of experience solving complex problems for customers and a strong knowledge of building applications, specifically using product analytics, feature flagging, or digital experience tooling. * You have excellent verbal and written communication skills. * Familiarity with product analytics platforms and optimizing them for Enterprise level production usage (e.g. Adobe Analytics, Google Analytics, Amplitude, Mixpanel, Heap, Contentsquare, FullStory, PostHog). * Fluent in the digital experience and product analytics market domain, competition, technological shifts, and customer needs related to feature flag management, experimentation, and session replay. * In-depth knowledge or experience with leveraging feature flag and experimentation tools (LaunchDarkly, Eppo, Split, Optimizely, etc.) and session replay platforms (FullStory, Contentsquare, Microsoft Clarity, etc.). * Someone who can analyze Codebase and understands CI/CD, branch strategies and how that can influence Feature Flags. * Experience with commonly used web and mobile languages and frameworks such as JavaScript, TypeScript, React, Python, iOS/Swift, Android/Kotlin, and file formats such as JSON and YAML. * You are comfortable operating in rapidly evolving, ambiguous technical domains. * You build deep context across teams and translate it into reusable, scalable solutions. * You take ownership from problem definition through implementation and measurable outcomes. * You are highly detail-oriented, particularly when working on architectures and customer-facing technical assets * You bring strong listening and consultative skills and are experienced supporting customers in high-pressure, complex situations. * Able to sit up to 4 hours, traveling to and from client sites. * Able to travel via auto, train, or air up to 40% of the time. Bonus Points: * Successful track record with 5+ years experience working as a Growth Engineering  * Experience using Datadog and/or other observability tools with Product Analytics, or Feature Flags. * Have proven experience deploying observability or analytics instrumentation in production environments at scale. * Background in experimentation program design, defining success metrics, guard rails, and statistical significance frameworks for A/B tests. * Experience with privacy-by-design and data governance for session replay, including PII masking, consent management, and data residency requirements in regulated industries. * Experience collaborating with open source projects and active engagement within associated communities. Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your skills, we encourage you to apply. Benefits and Growth:  * Best-in-breed onboarding * Generous global benefits * 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. #LI-Hybrid Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan. The reasonably estimated yearly salary for this role at Datadog is: $152,000—$222,000 USD ---------------------------------------------------------------------------------------------------------------------------------- About Datadog:  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. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. This form is for accommodation requests only and cannot be used to inquire about the status of applications.  Privacy and AI Guidelines: Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.