People Operations Generalist

About the role

Datarails is hiring a People Operations Generalist to support employee experience and HR operations across North America. In this fully remote position, you will be the main contact for many employee-facing HR needs, helping ensure people get quick, dependable support while People Operations stays efficient and scalable. You will work closely with the Chief of Staff, Human Resources, Talent Acquisition, Finance, IT, and the global HR team to support employees throughout their journey, from onboarding to growth and beyond.

This role is best suited for someone who enjoys improving the employee experience, solving problems, staying highly organized, and building smooth, effective processes. The position is 100% remote, but candidates must be based in the United States, within the Eastern time zone. Some travel is expected for company and team offsites. Relocation and visa sponsorship are not provided.

Employee experience and support

• Act as a first point of contact for everyday employee questions across North America.
• Hold regular one-on-one check-ins with employees to collect feedback and strengthen the employee experience.
• Help organize recognition moments such as life events, appreciation activities, holiday gifts, and engagement efforts.
• Support broader employee engagement programs.
• Raise employee relations, policy, and compliance matters to the appropriate stakeholders when needed.

HR operations

• Handle onboarding coordination for new hires in HiBob and Rippling.
• Keep employee records current and ensure HR system data remains accurate and reliable.
• Carry out promotions, org changes, employee lifecycle updates, and related system maintenance.
• Assist with annual merit review administration.
• Maintain HR documentation, workflows, and operational procedures.

Benefits administration

• Administer benefits programs in the U.S. and Canada, including health coverage, retirement plans, wellness options, and employee perks.
• Coordinate leave and PTO administration with internal partners.
• Serve as the main contact for employee benefits questions.
• Work with vendors to support and improve benefits offerings.

Programs and logistics

• Manage Working from Abroad requests.
• Oversee office reimbursement programs.
• Coordinate remote happy hours, in-person workdays, and offsite logistics for teams.
• Handle CPA renewals and track the People Operations budget.
• Administer Navan and other People Operations vendors.
• Support the launch of new employee programs and benefits.

Process improvement

• Look continuously for ways to simplify, automate, and scale People Operations work.
• Partner with internal teams to improve efficiency and strengthen the employee experience.
• Keep HR systems clean, structured, and dependable.

What success looks like

• Providing an excellent employee experience.
• Completing employee lifecycle tasks accurately and on time.
• Maintaining strong HRIS data quality and system administration.
• Running onboarding, promotions, and merit cycles smoothly.
• Administering benefits and employee programs effectively.
• Continuously improving People Operations workflows.
• Building trusted relationships with employees across North America.

Additional responsibilities

• Own the employee lifecycle for your assigned department, including onboarding and offboarding, regular employee check-ins, manager coaching, and proactive guidance.
• Partner with department leaders from team leads through executive level to understand their teams and support alignment between people goals and business goals.
• Work with the wider HR team on departmental processes and company-wide cycles such as performance reviews and salary reviews.
• Represent employee interests to leadership and act as a key contact for your department.
• Contribute to projects involving employee experience, people operations, and company structure in collaboration with the Chief of Staff for the Americas.

Qualifications

• At least 2 years of experience in Human Resources, People Operations, or a similar field, ideally in a startup environment.
• Background supporting employee lifecycle processes in a fast-moving setting.
• Experience handling employee benefits and HR programs.
• Familiarity with HRIS tools such as HiBob, Rippling, Workday, BambooHR, or comparable platforms.
• Strong organization and meticulous attention to detail.
• Excellent communication and customer service skills.
• Ability to juggle multiple priorities while staying accurate and responsive.
• Experience supporting remote or distributed teams is preferred.

Requirements

• 2 to 3 years of experience in a people-facing HR role such as HR generalist, employee experience, employee relations, or a similar function.
• Strong interpersonal communication skills and the ability to build trust at all levels of the organization.
• Comfort working in a changing environment where priorities shift often and the pace can be unpredictable.
• Professional judgment and discretion when handling sensitive matters.
• Preference for experience working with multicultural teams across time zones in a hypergrowth environment.
• Willingness and ability to meet the team in New York City several times a year and attend company offsites throughout the year.

What we offer

• Target base salary of USD 85,000 to 100,000 per year, depending on experience, skills, and location.
• Meaningful equity.
• 401(k) plan with up to 4% employer match.
• High-quality medical, vision, and dental coverage, with 100% employer-paid coverage for employees and generous support for dependents.
• Parental leave.
• Flexible PTO plus 12 paid company holidays.
• Life insurance.
• Additional benefits and employee offerings.

Equal opportunity

Datarails is committed to equal employment opportunity and building a diverse, inclusive workplace. Hiring and employment decisions are made without discrimination based on race, color, religion, national origin, gender, age, sexual orientation, disability, genetic information, gender identity or expression, veteran status, or any other legally protected characteristic. The company follows all applicable anti-discrimination and equal opportunity laws across recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leave, compensation, and training.