
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 looking for a Senior User Experience Designer to lead the evolution of our design system to enable faster, more
consistent product development across all products and platforms. Ultimately, you will empower our designers and engineers with a
high-leverage single source of truth that multiplies output and streamlines the entire development lifecycle. You are the keeper
of shared standards — the person who makes it easier for every designer and engineer to ship better work.
What you'll do
workarounds.
collaboration.
What you'll bring
tooling work in practice.
while maintaining a critical eye for quality and system integrity
Nice to haves
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
Senior Product Manager - Search Datadog’s Search team helps users – both human and agents – find answers to their questions. Search is a critical function in Datadog, and touches many product surfaces: the query editors in product homepages and dashboards, search bars for finding relevant assets, the global cmd+k navigation search, and the MCP tools that our Bits AI agent uses to respond to natural language prompts. Search is a full-stack team: owning user-facing search components, backend search ranking systems, and machine learning models to produce recommendations. The Search team is relatively new, and still growing. We have recently built out agentic search tools, and we are looking for a leader to help us expand to ambitious orchestration systems that deliver accurate results, and proactive recommendations across both keyword and semantic search. Beyond this, you’ll have room to influence how Datadog thinks about Search as a strategic surface. What you’ll do: * Define and deliver how Datadog's AI agents discover the right context and tools to answer natural-language questions accurately and at scale * Stay on top of industry trends in UI and agentic search experiences and capabilities * Collaborate with Applied AI teams to integrate ranking, personalization, and recommendation models that scale across both human and agentic users * Define and monitor KPIs for search quality, adoption, and downstream impact on user productivity; use them to drive data-informed decision making * Engage directly with customers and internal product teams to deeply understand search journeys across query editors, global navigation, and natural-language agent interfaces Who you are: * You have experience with search, ranking, or recommendation systems * You are familiar with or very interested in MCP servers and differences between human and agentic UX * You have a sharp eye for design and strong opinions on the micro-interactions — keyboard navigation, autocomplete behavior, loading states — that separate a good search experience from a great one * You have a strong technical background, and sense of the day in the life of an engineer operating large-scale data systems * You have excellent verbal and written communication skills and the willingness to present and defend your ideas to technical stakeholders and executives alike * You have 5+ years product experience 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. #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: $192,000—$240,000 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.
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.