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

Roll

Senior AI Engineer, AI Solutions

Kategori

Data/IT

Plats

Boston

Publicerad

1 maj

Sista ansökningsdag

16 augusti

Liknande jobb

Senior DevOps Engineer

Cargurus

Boston•Publicerad: 26 juni•Sista ansökan: 16 aug.

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. Our primary domains include: * Infrastructure Delivery: HCP Terraform workspaces, Terraform module registry governance, Sentinel and Semgrep policy enforcement, and self-service IaC paved paths for development teams. * Secrets Management: HashiCorp Vault implementation, dynamic short-lived credentials, PKI/CA, and supporting the rollout of zero-static-credential patterns across production workloads. * CI/CD Platform: GitHub Actions maturity (GHES, GitHub Connect, org-scoped runners), Concourse infrastructure, and pipeline supply-chain security. * AWS Self-Service: No-code and IaC-driven provisioning for S3, Lambda, ElastiCache, and expanding the self-service catalog to new resource types. * AI Infrastructure Governance: Governed Amazon Bedrock access, per-team token quotas and cost dashboards, Bedrock Savings Plan management, and developer AI tooling (Claude Code, GitHub Copilot) governance. * Platform Integrity: Sentinel/Semgrep policy maturity, shift-left guardrails, pipeline hardening, and cloud maturity model advancement. What you'll do * Platform Delivery & Technical Ownership: Own the technical execution and delivery of significant platform capabilities. Author 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. * IaC Platform & Policy Engineering: Manage HCP Terraform workspaces, the Terraform module registry, and Sentinel/Semgrep policy implementations. Calibrate hard vs. advisory guardrails, eliminate false positives, and expand coverage as new resource types onboard to self-service. * Secrets & Security Integration: Accelerate Vault adoption across CarGurus workloads — handling dynamic secrets, PKI/CA, transit encryption, and AWS dynamic IAM credentials. Execute the tactical roadmaps toward zero standing long-lived credentials in production. * AI Infrastructure Governance: Maintain and operate our governed Amazon Bedrock platform, implementing per-team access controls, cost attribution, anomaly detection, and self-service access patterns. Assist in extending governance to developer AI tooling (Claude Code, Copilot) as adoption scales. * Developer Enablement & Self-Service: Expand the AWS self-service catalog and paved-path IaC offerings so teams can provision, operate, and own cloud resources independently. Monitor adoption metrics and use feedback to prioritize the next platform investments. * CI/CD & Pipeline Integrity: Execute GitHub Actions maturity initiatives including GitHub Connect adoption, org-scoped runner 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. * Mentorship & Code Quality: Actively grow teammates' capabilities through thorough code and IaC reviews, pairing on complex problems, and sharing context and patterns that help the immediate team move more independently. Contribute to team coding standards and documentation. * Cross-Team Collaboration: Partner with adjacent teams (Cloud Infrastructure, SRE, DevX, and product engineering) to align on technical concerns at team boundaries. Represent Cloud Enablement's perspective clearly in shared discussions and help resolve integration ambiguity. * Incident Management & Reliability: Participate in the team's on-call rotation and incident response. Apply incident learnings to improve platform reliability and reduce toil for the team and its customers. * AI-Assisted Engineering: Actively incorporate AI tooling (Claude Code, GitHub Copilot, Amazon Q) into your engineering workflow — from generating and reviewing IaC to accelerating architecture exploration and incident triage. What you'll bring * 4+ years of professional experience in a hands-on DevOps, platform engineering, or cloud infrastructure role, performing the core responsibilities of this position. * Cloud Infrastructure Depth: Significant experience operating production workloads in AWS including IAM, S3, Lambda, EKS, ElastiCache, EC2, and related services. Comfortable reasoning about security, cost, and reliability trade-offs at platform scale. * Infrastructure as Code & Policy Engineering: High proficiency with Terraform, including HCP Terraform, remote state, module design, and workspace governance. Hands-on experience with Sentinel and/or Semgrep for policy-as-code enforcement. * Secrets Management: Practical experience with HashiCorp Vault dynamic secrets, PKI/CA, AppRole/Kubernetes auth, or transit encryption. Experience migrating workloads from static credentials to short-lived credential models. * CI/CD & Platform Engineering: Deep experience with GitHub Actions runner infrastructure, composite actions, GHES/GHEC, and supply-chain security practices. Familiarity with CircleCI or similar pipeline systems. * FinOps & AI Awareness: Ability to reason about cloud cost attribution, resource tagging strategies, and FinOps tooling (e.g., CloudZero, AWS Cost Explorer). Familiarity with Amazon Bedrock, LLM API cost structures, and basic governance considerations (spend attribution, access controls). * Programming & Automation: Proficiency in at least one scripting/programming language (Python, Go, or similar) for building automation, CLI tooling, and platform integrations. * Systems Thinking & Communication: Able to distill complex technical problems into clear design docs, written proposals, and 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 $137,000—$171,000 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

Senior Product Solutions Architect - LLM Observability

Datadog

Boston•Publicerad: 18 juni•Sista ansökan: 16 aug.

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.

Senior UX Designer, Design System

Cargurus

Boston•Publicerad: 22 apr.•Sista ansökan: 16 aug.