You could work anywhere. Why us? - Join a pre-IPO startup with capital, traction and runway ($240M funded | 40X revenue growth in 4 years | $2T market size) - Work closely with brilliant leaders and team mates from companies like Nvidia, Better, McKinsey, etc. - Disrupt a massive market and take us to a $5B business in the next few years - Be immersed in a talent-dense environment and greatly accelerate your career growth About the opportunity: We are hiring a Senior People Operations Manager to lead the operational foundation of our People function. This role will own the day-to-day and strategic execution of payroll, benefits, HR compliance, employment taxes, HR systems, immigration coordination, and global workforce operations (including EOR management). This role will also manage a distributed People Operations support team (two Philippines-based associates) responsible for daily execution and employee support workflows. You will set priorities, ensure operational rigor, and raise the bar on accuracy, documentation, and service delivery as the company scales. This position partners closely with our HRBP lead, who will focus on employee relations, performance management, talent density, and leadership support—while you ensure the systems and operations behind the employee experience are consistent, compliant, and scalable. This position can be fully remote from AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NY, NV, OR, TN, TX, UT, VA, or Ontario, Canada, or onsite/hybrid from Palo Alto, New York, or Toronto. Key Responsibilities: People Operations & Team Leadership: - Team Management: Lead a distributed offshore People Ops team; provide coaching and structure to two direct reports. - Service Delivery: Establish workflows, quality standards, and SLAs for onboarding, payroll, and benefits. - Process Excellence: Drive HRIS data integrity, automation, and self-service to reduce manual work and scale operations. Building and utilizing AI tools to automate and optimize HR processes. Payroll, Benefits & Finance: - Payroll Ownership: Oversee end-to-end payroll processing, tax withholding, and year-end reporting (W-2s) for all populations. - Benefits Strategy: Lead open enrollment and manage the full suite of health and retirement programs, vendor performance, and broker relations. - Global Operations: Manage EOR partnerships for international employees, including contract updates and cost forecasting with Finance. Compliance, Risk & Lifecycle: - Regulatory Oversight: Own the compliance calendar (federal, state, local) and lead audits for payroll and documentation. - Employee Lifecycle: Oversee onboarding/offboarding execution and streamline operational handoffs with IT and Legal. - Mobility: Coordinate with counsel to manage immigration filings, visa tracking, and work authorization support. What Success Looks Like: - Payroll and benefits run smoothly, with minimal escalations and high employee trust. - Compliance processes are proactive, organized, and audit-ready at all times. - EOR and immigration workflows are predictable, well-managed, and low-risk. - Associates are well-supported and operating with clarity, accountability, and strong quality standards. - People Ops runs as a scalable service function—fast, accurate, and consistent. Qualifications: - 7+ years of progressive People Operations experience, including payroll, benefits, and compliance ownership at a fast-growing startup that scaled from 150 to 350 employees. - Experience managing a distributed or offshore operations team is strongly preferred. - Strong understanding of multi-state employment compliance and operational risk management. - Experience partnering with external vendors (payroll, benefits, EOR, immigration counsel). - High attention to detail and strong judgment handling confidential employee data. - Strong project management skills and ability to execute against deadlines. Preferred Qualifications: - Experience managing EOR platforms (Deel, Remote, Rippling Global, Oyster, Papaya, etc.). - Familiarity with immigration support processes and vendor coordination. - Experience in a high-growth startup environment. - HRIS expertise and comfort driving process automation. While we appreciate your interest and application, only applicants under consideration will be contacted. Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai: Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.

Rush Street Interactive (NYSE: RSI) is a market leader in online casino and sports betting, currently operating real-money gaming with our brands: BetRivers.com, PlaySugarHouse.com, and RushBet.co. We’re building bridges between online, social and land-based gaming businesses to create amazing, integrated experiences that keep players in the game. The People Operations Specialist supports employee lifecycle processes by managing Workday transactions, maintaining accurate employee data, and ensuring compliance with internal policies and regulatory requirements. This role partners with Compliance, Legal, and cross-functional teams to support People Operations processes globally while serving as a subject matter expert for North America. Responsibilities include responding to escalated inquiries, supporting audits and compliance requests, generating reports, supporting payroll and benefits, documenting and maintaining processes, and identifying improvements to ensure efficient and consistent People Team operations What You'll Do: - Process employee lifecycle transactions including hires, transfers, promotions, leaves of absence, and terminations in Workday and other People Team systems - Maintain accurate and complete employee records and ensure data integrity through regular audits and data validation - Provide operational support and guidance for employee lifecycle processes, ensuring consistency and adherence to established procedures - Maintain US workers’ compensation codes in Workday, conduct periodic audits, and coordinate required insurance filings - Maintain global employment document templates and coordinate annual reviews with the Legal team - Respond to employee, manager, and vendor inquiries escalated by People Coordinator(s) regarding People Team policies, procedures, and systems - Support internal and external compliance requirements including recordkeeping, documentation management, and responding to internal audit requests by gathering and validating employee records and supporting documentation - Support People Operations processes globally while serving as a subject matter expert for North America, specifically Canada, ensuring adherence to applicable employment standards, compliance requirements, and internal policies - Partner with external Payroll and Benefits teams to ensure accurate employee updates and support related processes - Generate and maintain standard and ad hoc People data reports from Workday to support operational and compliance needs - Document and continuously improve People Operations workflows, processes, and system utilization - Assist in training and onboarding People Coordinators or other junior team members - Partner with cross-functional teams to ensure consistent People Team practices and positive employee experience - Support additional tasks or projects as assigned by the Manager, People Operations What You'll Bring: - Bachelor’s Degree in HR, Business, or a related field - 3+ years of Human Resources experience - Strong knowledge of US and Canada operational employment laws, benefits, payroll, and People Team processes - Strong problem-solving and critical thinking skills - Excellent written and verbal communication skills - Demonstrated discretion, professionalism, and sound judgment when handling confidential or sensitive information - Ability to identify opportunities for improvements aligned with business needs and People Team policies - Highly organized with strong attention to detail and the ability to manage multiple priorities - Proficiency in Workday reporting and processing employee lifecycle transactions - Strong collaboration skills with the ability to cultivate positive working relationships across teams - Proficiency in Microsoft Office Suite (Excel, PowerPoint, Word) - Familiarity with ADP, Confluence, and Jira, preferred. - Project management experience supporting People initiatives, preferred. - Experience in a regulated industry, preferred. - Basic knowledge of SOX compliance and its application to People Team processes, preferred. - Able to travel occasionally both domestically and international #LI-REMOTE This role spans a wide breadth of experience at Rush Street Interactive, welcoming candidates with diverse experiences, backgrounds, and locations. The pay range reflects potential variations in experience, skills, and location. The pay range does not reflect total compensation, which includes base pay, benefits, and/or bonuses. For candidates outside the US (Canada, Europe, Latin America), we take a locally informed approach to compensation and will share specific ranges based on your country of residence. Location Eligibility (for nationwide roles): Open to candidates across the U.S. Location Eligibility (for other roles): Location requirements may vary and will be specified in the job posting. Benefits: - Discretionary annual company bonus (Eligibility Varies by Role) - 401(k) plan with 100% company match on the first 4% - Comprehensive medical coverage (HSA & FSA plans), dental, and vision insurance - Paid Time Off (Eligibility Varies by Role) - Employee Assistance Program (EAP) Pay Range $60,000—$70,000 USD What Makes Us Great: - Comprehensive compensation - Work-life balance initiatives - Autonomy – we embrace personal freedom and responsibility - Creativity – we are open to new ideas of how we can be better - Growth – we want you to develop personally as well as professionally - Top-notch professionals who are passionate about what they do - People-oriented environment and supportive atmosphere As a rapidly growing company in an emerging industry, you’ll have a huge impact on our product and our company. We like proactive team members and strive to have a company of self-disciplined professionals who enjoy collaboration, having fun, and of course, achieving together what others believe to be improbable. We are dedicated to treating everyone with respect and to support your professional and personal growth. Rush Street Interactive is an equal opportunity employer and committed to a diverse and inclusive workplace. All qualified applicants will be considered for employment without regard to race, national origin, ancestry, sex, sexual orientation, sexual identity and expression, marital status, family status, lifestyle, age, culture, religion, military and veteran status, citizenship, or disability. Be at the forefront of this ground-breaking industry! Apply now! Rush Street Interactive uses AI-assisted tools at select stages of the hiring process to enhance efficiency, consistency, and communication. AI does not make hiring decisions - final decisions are made exclusively by our recruiting and hiring teams.

• Conduzir processos seletivos ponta a ponta para áreas comerciais, atendimento, tecnologia, marketing e áreas regulatórias. • Desenvolver estratégias de atração de talentos compatíveis com o perfil de startup em expansão. • Estruturar trilhas de entrevistas por competência e avaliar aderência cultural. • Implementar e acompanhar o processo de integração de novos colaboradores. • Garantir alinhamento com cultura organizacional, compliance e padrões regulatórios. • Acompanhar períodos de experiência e indicadores de adaptação e performance inicial. • Apoiar a construção de metas individuais e indicadores de performance. • Conduzir ciclos de avaliação de desempenho e feedback estruturado. • Aplicar pesquisas de clima e propor planos de ação. • Acompanhar lideranças no desenvolvimento de times de alta performance. • Monitorar métricas como turnover, absenteísmo, custo por contratação e tempo médio de recrutamento. • Gerar relatórios estratégicos para diretoria.

You could start your People Operations career anywhere. Why join Jerry.ai? Your car and your home are the two most expensive things you’ll ever own — and the hardest to manage. At Jerry, we’re building the first super app to help everyday Americans take control of both. From insurance and financing to repairs, we’re reimagining what it means to own and maintain your car and home. This is a $5 trillion+ problem — and we’re the only company tackling it end to end. Join us as our People Operations Associate and be a critical member of our rapidly growing team. This is a unique opportunity to directly influence how we support our most important asset — our people. If you're a driven individual eager to learn and grow your career in People Operations, we want to hear from you! How you’ll make an impact: - Work on a mission that matters: Help over 90% of Americans reduce financial stress and gain control over their most important assets. - Empower our teams: Support the end-to-end employee lifecycle — from ensuring seamless onboarding to organizing important company events. - Accelerate our trajectory: With 5M+ customers, $240M raised, and 60X revenue growth in 6 years, your work will directly enable us to become a $10B consumer company by 2030. What you’ll own: - Support our employee journeys: Support the end-to-end experience for all of our employees, from onboarding new hires to managing employee transitions. - Be our culture ambassador: As a remote first company, we are increasing our investment in in-person gatherings. You will play a key role in planning, organizing, and executing company-wide and team events (e.g., offsites, in-person and virtual events) and other culture-building initiatives. - Aid our internal communications efforts: Ensure information flows effectively across the organization by drafting and distributing internal communications such as the company-wide newsletters and periodic company updates. - Data & System Management: Ensure data accuracy and integrity within our HR systems and records, while handling administrative tasks such as I-9 verification, benefit administration and employment verification letters. - Process Optimization: Proactively identify opportunities to streamline People Operations workflows, leveraging AI and other tools to automate backend processes. Who you are: - You’re passionate about people and making a real impact on a company’s most valuable asset. - You are an excellent communicator, both written and live. - You're meticulous and detail-oriented. - You are well-organized and love to support multiple projects and teams while balancing excellence and speed. - You thrive in ambiguity and fast-paced environments. - You are resourceful and creative – you take the initiative to get things done well the first time. - You're mature and professional, and can handle sensitive information with the utmost discretion. What you bring: - Bachelor's or Master's degree in Human Resources, Business Administration, Psychology, Sociology, or a related field. - Experience or interest in HR, People Operations or related, ideally within a fast-paced startup environment While we appreciate your interest and application, only applicants under consideration will be contacted. Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai: Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.