People Operations Specialist

Cargurus

Who we are At CarGurus (NASDAQ: CARG), our mission is to give people the power to reach their destination. We started as a small team of developers determined to bring trust and transparency to car shopping. Since then, our history of innovation and go-to-market acceleration has driven industry-leading growth. In fact, we’re the largest and fastest-growing automotive marketplace, and we’ve been profitable for over 15 years. What we do The market is evolving, and we are too, moving the entire automotive journey online and guiding our customers through every step. That includes everything from the sale of an old car to the financing, purchase, and delivery of a new one. Today, tens of millions of consumers visit CarGurus.com each month, and ~30,000 dealerships use our products. But they're not the only ones who love CarGurus—our employees do, too. We have a people-first culture that fosters kindness, collaboration, and innovation, and empowers our Gurus with tools to fuel their career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives. Come join us for the ride! Role overview The Associate People Operations Specialist provides administrative and operational support across benefits, payroll, HR systems, and employee lifecycle processes. This role is critical to delivering accurate, compliant, and high-quality People Operations support while enhancing the overall employee experience. The role focuses on executing established workflows, maintaining employee and benefits data, managing vendor coordination, and responding to employee queries. The ideal candidate is detail-oriented, technically proficient, and capable of managing multiple priorities across global programs. What you'll do BENEFITS ADMINISTRATION & VENDOR MANAGEMENT * Manage global benefits operations across the US, Canada, UK, and Ireland, overseeing benefit administration, invoice tracking, and the processing and reconciliation of payments across approximately 20 vendors (including medical, dental, and life insurance) * Conduct monthly audits of benefit plans, identifying discrepancies and driving resolution * Administer global pension and retirement schemes (UK, Ireland, US), including system uploads and quarterly fee tracking * Oversee FSA/HSA funding aligned with payroll cycles, including quarterly employer contributions * Administer COBRA processes and maintain associated tracking documentation * Manage Evidence of Insurability (EOI) approvals and send follow-ups for pending submissions   HR Systems & Data Management * Maintain accurate employee data across Workday and related systems * Review and approve Qualified Life Event (QLE) benefit changes, including manual FSA/HSA adjustments * Process benefits onboarding, employee changes, beneficiary updates, and one-time employee payments (e.g., bonuses, reimbursements). * Monitor and troubleshoot weekly benefits integration files to ensure data accuracy and integrity * Run and review reports including Terminated with Benefits, Business Process Transactions, and quarterly dependent/beneficiary audits   Employee Support & Communications * Manage employee queries via ticketing systems (e.g., JIRA) * Provide support for benefits platforms and respond to FAQs * Coordinate employee communications, including onboarding reminders, benefits education, and wellness program updates * Maintain global Benefits Wiki and internal documentation, ensuring accuracy and accessibility   Programs & Operational Support * Administer commuter and parking programs, including enrollments, terminations, and funding file coordination * Plan and coordinate on-site and virtual events, including the annual Open Enrollment Fair * Support absence tracking, time-off administration, and other operational tasks that enhance employee experience and team efficiency Payroll & Compliance * Manage employee payroll deductions for Ireland and UK benefits * Support unemployment claim documentation and responses * Ensure compliance with regulatory requirements across benefits, payroll, and related programs   What you'll bring * 1–2 years of experience in benefits administration or HR operations * Strong  proficiency in Google Sheets (or Microsoft Excel) to organize and analyze data, with a solid grasp of Pivot Tables and functions like VLOOKUP. Experience with HRIS systems, particularly Workday Benefits Administration module * Comfort working with data and systems * Strong data entry and reconciliation capabilities * Familiarity with benefits administration platforms across US / UK / IE  * Understanding of system integrations and troubleshooting * Working knowledge of benefits regulations across all locations (US/ UK/ IE), including COBRA, FSA/HSA administration, pension contributions and associated tax implications (i.e UK/IE pension auto-enrolment and payroll deductions for medical/dental benefits) * Basic understanding of life insurance and Evidence of Insurability processes * Familiarity with payroll processing and vendor management   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 $57,000—$72,000 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

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 We are seeking a Benefits Analyst to be based in our Boston, MA, global headquarters location, on a hybrid schedule. This role will be reporting to the Director of Benefits and will be responsible for the oversight and administration of several CarGurus’ North America Benefits programs and perks as well as heavy involvement in new initiatives. This role will collaborate closely with both internal and external stakeholders and partners to optimize benefits offerings and provide excellent service to employees. What you’ll do  * Participate in all areas of employee benefits in partnership with the rest of the team. Lead a few areas of benefits.  50% of the work to start will be managing leave and accommodation cases end-to-end, partnering with vendors to ensure timely and accurate execution, and clear collaboration and communication with HR Strategy Partners, claimant employee and their manager. * Provide guidance and education to employees and managers; act as a subject matter expert on benefits programs. * Monitor vendor performance, data, and reporting; identify issues and hold partners accountable to service levels. * Collaborate cross-functionally (People Operations, People Applications (HRIS), Payroll, Legal, vendors) to ensure smooth program delivery. * Maintain confidentiality while ensuring compliance with legal and company requirements. * Support audits, reporting, and analysis; identify trends and recommend improvements. * Contribute to projects and program enhancements, vendor RFPs, and key initiatives like Annual Open Enrollment. * Partner with the Benefits team to meet priorities and escalate when needed. * Create employee communications for assigned programs. * Maintain ~60% onsite presence, with flexibility during peak periods. What You’ll Bring * 3+ years of U.S. benefits experience, preferably in fast paced, growing tech environments. * Experience in some  functions of employee benefits administration, including health and welfare, well-being, life and disability, leaves, 401(k), and voluntary plans. Time off, leaves and accommodations administration experience, as well as a passion for well-being are a plus. * Proven examples of independently owning several areas of benefits responsibilities, including careful tracking, accountability and clear communication with all critical stakeholders a must. * Examples of working collaboratively in a team environment. * Affinity for educating and communicating on employee benefits, including presenting to audiences. * Appreciation for compliance and risk reduction with comfort in and knowledge of local, state and federal employee benefits regulations, such as ERISA, IRS, DOL, ACA, HIPAA, and COBRA. * Examples of successfully completing special projects on top of normal day to day responsibilities. * High level of integrity and discretion when handling sensitive employee information. * Robust analytical skills, with the ability to interpret data and make data-driven recommendations. * Attention to detail and accuracy. * Comfort and proficiency with computer software and HRIS systems (Google products and Workday experience a plus). 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 $72,000—$91,000 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

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 We're seeking a proactive, independent self-starter to lead project management for our People & Talent organization. This is your opportunity to shape how critical people work gets done—driving clarity, consistency, and flawless execution across a growing organization while partnering directly with leaders on initiatives that impact every employee and our bottom line. As our Senior Project Manager, you'll own cross-functional programs and projects that span multiple P&T functions and the broader business, reporting to the Senior Director, Compensation & People Operations. You'll oversee much of our program and project portfolio, lead quarterly and annual planning efforts, and ensure crystal-clear ownership, smart prioritization, and on-time delivery of our most important work. This role demands someone who can communicate effectively with employees at all levels—from individual contributors to executives—to drive our P&T outcomes forward. You'll partner closely with P&T leadership, functional leads, and business stakeholders to execute high-impact initiatives aligned to organizational goals, while enabling consistent delivery through standards, frameworks, coaching, and portfolio-level oversight. Subject matter experts retain accountability for their project outcomes; you provide the strategic backbone that makes it all happen. What you’ll do Program & Project Delivery * Partner with project sponsors and stakeholders to define scope, deliverables, timelines, success metrics, resources, and governance for People & Talent Initiatives. * Lead cross-functional P&T programs and projects from initiation through delivery, ensuring alignment to quarterly and annual P&T goals. Identify key requirements needed from cross-functional teams and external vendors as appropriate. * Track and manage interdependencies across teams to ensure predictable delivery and accountability. * Assist P&T leadership with ad hoc tasks that contribute to our multi-year strategy. Portfolio, Planning & Capacity Management * Own P&T program and project portfolio management, including prioritization and alignment with quarterly planning and annual objectives. * Support quarterly planning efforts by assessing demand, sequencing work, and facilitating trade-off discussions. * Partner with leaders on P&T capacity planning to balance workloads across planned and unplanned initiatives. * Support Comp & Audit Committee–related project planning and execution. Governance, Communication & Change Management * Establish clear governance models including approval paths, decision tracking, and escalation mechanisms. * Provide regular, concise updates to leadership on project status, risks, dependencies, and mitigation strategies. * Partner with stakeholders on change management, communications, and adoption strategies to ensure sustainable outcomes. PMO Capability & Standards * Develop and continuously improve project management standards, routines, and frameworks for P&T. * Build PM capability across the organization through templates, tooling, coaching, and best practices. * Ensure consistent, transparent reporting across programs and projects. What you’ll bring * 8+ years of experience leading medium-to-large, cross-functional programs and projects, including enterprise-wide initiatives; experience within a People & Talent or HR function strongly preferred. * Proven experience establishing PMO practices, project governance, or portfolio management in a matrixed organization. * Strong leadership and facilitation skills with the ability to influence without direct authority. * Experience applying change management principles and measuring adoption and outcomes. * Comfort partnering with leadership, legal, finance, engineering, and all people & talent teams and navigating complex dependencies. * Strong analytical judgment and ability to operate effectively in ambiguous, fast-changing environments. * Demonstrated success defining and tracking KPIs for project performance and portfolio health. * Bachelor’s degree required; master’s degree preferred in business, engineering, or a related field. * Strong working knowledge of Agile practices and methodologies.   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 $117,000—$146,000 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