
Cargurus · Boston
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 ...
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
CarGurus is seeking a Senior DevOps Engineer to join our Cloud Enablement team. This team builds and operates the cloud platform
capabilities, automation, and guardrails that help engineering teams provision infrastructure, deploy services, and work securely
in the cloud with less friction.
In this role, you will contribute to the design, implementation, and operation of scalable platform services that improve
developer experience, strengthen reliability, and support self-service infrastructure across the company. We are looking for an
engineer who is hands-on, execution-oriented, and motivated by building practical solutions that other engineers rely on every
day.
enforcement, and self-service IaC paved paths for development teams.
zero-static-credential patterns across production workloads.
supply-chain security.
new resource types.
management, and developer AI tooling (Claude Code, GitHub Copilot) governance.
advancement.
What you'll do
design docs and contribute to Architecture Decision Records (ADRs) for team-level decisions. Lead complex, multi-sprint
initiatives (e.g., Vault dynamic secrets rollout, GitHub Actions maturity, AWS Sandbox self-service) end-to-end through to
production.
implementations. Calibrate hard vs. advisory guardrails, eliminate false positives, and expand coverage as new resource types
onboard to self-service.
encryption, and AWS dynamic IAM credentials. Execute the tactical roadmaps toward zero standing long-lived credentials in
production.
cost attribution, anomaly detection, and self-service access patterns. Assist in extending governance to developer AI tooling
(Claude Code, Copilot) as adoption scales.
operate, and own cloud resources independently. Monitor adoption metrics and use feedback to prioritize the next platform
investments.
observability, bundled action governance, CircleCI adoption and migration, and pipeline supply-chain hardening. Ensure teams
can deliver reliably on modern, self-owned CI/CD infrastructure.
problems, and sharing context and patterns that help the immediate team move more independently. Contribute to team coding
standards and documentation.
technical concerns at team boundaries. Represent Cloud Enablement's perspective clearly in shared discussions and help resolve
integration ambiguity.
to improve platform reliability and reduce toil for the team and its customers.
— from generating and reviewing IaC to accelerating architecture exploration and incident triage.
What you'll bring
core responsibilities of this position.
ElastiCache, EC2, and related services. Comfortable reasoning about security, cost, and reliability trade-offs at platform
scale.
design, and workspace governance. Hands-on experience with Sentinel and/or Semgrep for policy-as-code enforcement.
encryption. Experience migrating workloads from static credentials to short-lived credential models.
supply-chain security practices. Familiarity with CircleCI or similar pipeline systems.
CloudZero, AWS Cost Explorer). Familiarity with Amazon Bedrock, LLM API cost structures, and basic governance considerations
(spend attribution, access controls).
automation, CLI tooling, and platform integrations.
stakeholder-facing summaries. Comfortable working across teams to align on shared technical boundaries.
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
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
The Synthetics Product is a critical pillar of Datadog’s digital experience monitoring portfolio, enabling customers to proactively test, monitor, and optimize the availability and performance of their applications and user journeys. As the Product Solutions Architect (PSA) for Synthetics, you will work closely with Datadog customers and the Synthetics Product and Engineering teams in helping Synthetics users architect, implement best practices, and adopt Datadog at scale. SAs ensure that customer needs have been met and that the solution is fully functioning according to business requirements, governance, and compliance goals. SAs are accountable for the outcome of these initiatives, and frequently collaborate with other Datadog resources to drive measurable success. 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 the Product Expert on Datadog Synthetics Product. * Offer guidance on architecture choices, data collection, and best practices to large Enterprise customers as they adopt these Datadog services across the organization at scale. * Be a Trusted Advisor to Product Management by providing high quality feedback based on your field experience working closely with our Support, Partners, and Customers. * Capture repeat customer use cases and solutions and in turn publish Reference Architectures and Implementation Guides for Datadog prospect and customer consumption. * 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 Synthetics Product amongst the Digital Experience product suite at Datadog. * Exercise the products you represent by building small scale deployments and proofs of concepts to verify proposed solutions and reproduce customer environments. Who You Are: * Someone with strong experience of synthetics products * Someone who can dive deep into our Codebase, SDKs, and GitHub processes. * Experience with JSON and YAML configuration files, and Terraform for Infrastructure as Code in CI/CD workflows. * A self-starter, tech-savvy professional, who is comfortable working with bleeding edge technology and processes, even if it hasn’t been well defined. * A deep learner and a Subject Matter Expert today that has built advocacy and knowledge across multiple teams with the knowledge you possess. * Strong understanding of client-side, frontend, and backend application performance measurement, including synthetic testing strategies, performance indicators, and common failure modes * Fluent in understanding the observability market domain, competition, technological shifts, and customer needs, especially specific to synthetics. * Constantly finding new and unique solutions to solve hard problems. * A person who possesses exceptional listening and consultative skills, for both internal and external audiences. * Experienced working with customers in high pressure situations where the solution is sometimes not obvious. * 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 an Architect or Consultant. * In-depth knowledge or experience with leading Observability tools (Datadog, New Relic, AppDynamics, Dynatrace, etc.) * Experience using Datadog and/or other observability tools in an SRE or DevOps capacity. * Experience with application performance tuning. * Have proven experience deploying observability in production environments at scale. * Experience collaborating with open source projects and active engagement within associated communities. * Experience educating customers on AI-enabled systems, including setting expectations around non-deterministic behavior, variability in outputs, and how to design reliable workflows and user experiences around these characteristics 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: * Generous and competitive benefits package * New hire stock equity (RSUs) and employee stock purchase plan * Continuous career development and pathing opportunities * Employee-focused best in class onboarding * Internal mentor and cross-departmental buddy program * Friendly and inclusive workplace culture * Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog. 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: $167,000—$244,000 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.
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. Datadog’s LLM Observability product enables organizations to monitor, troubleshoot, and optimize large-scale LLM-powered applications with confidence, while meeting requirements around data privacy, compliance, and cost management. As a Product Solutions Architect, you will partner closely with Datadog customers and the LLM Observability product team to design architectures, implement best practices, and drive adoption of LLM observability 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 the in-house subject matter expert for Datadog’s LLM Observability product * Partner with Field teams to provide hands-on technical and architectural guidance to enterprise customers adopting LLM Observability * Create high-impact technical collateral, including reference architectures, technical guides, cookbooks, and documentation to enable Field teams and the broader customer community * Build proofs of concept and small-scale deployments to validate solutions and reproduce real-world customer environments * Act as a trusted advisor to Product Management by delivering actionable feedback informed by real-world field experience Who You Are: * You bring a strong software engineering foundation, with hands-on experience building and operating LLM-powered applications in production environments at a large scale, and are comfortable diving deep into codebases to understand architectural decisions, tradeoffs, and implementation details * You are familiar with distributed systems and core observability concepts, such as tracing, metrics, and logging, and can translate those patterns into the emerging LLM observability domain, including LLM spans, evaluations, and prompt templates * Experience with languages such as Python and/or JavaScript/TypeScript * 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 * 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 Solutions Architect or Sales Engineer supporting the AI space * Experience using Datadog and/or other observability tools in an SRE or DevOps capacity * Experience with LLM application evaluation and testing frameworks 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. 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: $167,000—$244,000 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.
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. The Product Solution Architecture team works closely with Datadog customers, Datadog’s Product management, engineering and Tech Solutions teams to help architect and implement the Datadog Solution. The team has grown to cover more than 12 Product Categories and needs a highly motivated, results-oriented individual to help lead the team. 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: * Manage a team of expert individual contributors, working with Engineering and Product Management on their Product, who help create best practices for adoption of Datadog at scale. * Assist in recruiting and hiring of top talent for the team. * Mentor/coach new hires during on-boarding to ensure proper ramping of skills and capabilities * Ensure that your team is aligned to top company initiatives and enabled to work with various Datadog internal and external stakeholders * Deliver performance reviews along with collaborating on and executing individual development plans * Be a Trusted Advisor to Product Management by providing high quality feedback based on your field experience working closely with our Sales, Support, Partners and Customers * Offer guidance on architecture choices, data collection, and best practices to large Enterprise customers as they adopt these Datadog services across the organization * Participate in Executive Brief conversations with high profile customers and prospects about overall architecture, Observability Best Practices and industry trends Who You Are: * 10+ years of experience solving complex problems for customers and a strong knowledge of observability space. * 5+ years of people management experience. * Experienced in interacting and influencing key stakeholders (VPs, C level) in large organizations * You have excellent verbal and written communication skills * Fluent in the monitoring market domain, competition, technological shifts and customer needs * Proven in your ability to grow and develop a team * Experienced in recruiting both individual contributors and front line leaders * Able to think strategically and creatively about a wide variety of challenges 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. 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: $211,000—$309,000 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.