Senior Product Solutions Architect - LLM Observability

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 CarGurus is transforming how the company operates by embedding AI into workflows across every function — product, engineering, revenue, finance, support. It’s a software engineering role where the domain is the entire business. You’ll work directly with teams across the org to understand how work actually gets done, identify where AI can change the unit of work or shift where judgment lives, and build the systems that make it real. Some of that is agent-based automation. Some of it is workflow redesign. All of it requires someone who can architect and ship production-quality software, not stitch together SaaS integrations. This is not a Salesforce developer, Boomi connector, or low-code/no-code position, nor is it an enterprise architect or ML model training role. This is a small, high-autonomy team reporting to the Head of AI Solutions. You’ll have outsized influence on how a publicly traded company with ~$1B in revenue adopts AI — not as a pilot or a demo, but as a structural change in how the business runs. You will be successful here if you are a product-caliber engineer who finds internal workflow transformation genuinely interesting — not a consolation prize, but the most leveraged place to be right now. You’d rather build something real that 200 people use tomorrow than something polished that ships in 6 months. What you'll do * Design and build AI-powered workflows and agent-based systems that transform how teams operate across the company. * Partner directly with stakeholders in revenue, product, engineering, finance, and operations to gather requirements, map existing workflows, and identify high-leverage opportunities for AI. * Build end-to-end — from scoping and architecture through implementation and deployment. This team ships, it doesn’t hand off specs. * Work with AI APIs and platforms (Anthropic/Claude, AWS Bedrock, and others) to build agentic systems, automation pipelines, and intelligent tooling. * Operate across a messy, heterogeneous environment — AWS infrastructure, Salesforce, internal services — without waiting for everything to be clean before you start building. * Help shape the technical strategy and standards for AI Solutions as a function. What you'll bring * 5+ years of relevant software engineering experience. * Strong software engineering fundamentals — you’ve built and shipped production systems, not just prototypes. * Proficiency in Python as the primary language for this work; comfort with additional languages is a plus. * Experience designing APIs, services, and data pipelines. You think in systems, not scripts. * AWS fluency — you’re comfortable working within AWS infrastructure and services. * Hands-on experience building with LLM APIs, agent frameworks, or AI-powered applications — not just experimentation, but something that ran in production or was used by real people. * Ability to operate with high autonomy. You’ll scope your own work, make architectural decisions, and own outcomes. * Willingness to work across the full stack of a business — including systems like Salesforce that aren’t glamorous but are where the high-impact problems live. Nice-to-haves: * Experience with workflow orchestration or automation at scale. * Familiarity with Salesforce APIs and integration patterns (not Salesforce administration). * Background in recommendations, search, data science, or ML engineering. * Experience working cross-functionally with non-technical stakeholders.   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 $144,000—$181,000 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

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.

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. 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.