People Operations Generalist

At Datarails, our people are at the heart of everything we do. We're looking for a People Operations Generalist to help deliver an exceptional employee experience across North America by owning the day-to-day operations that support our growing team.

This role serves as the primary point of contact for many employee-facing HR processes, ensuring employees receive timely support while helping maintain efficient, scalable People Operations. You'll partner closely with the Chief of Staff, Human Resources, Talent Acquisition, Finance, IT, and our global HR team to support employees throughout their lifecycle, from onboarding through career growth and beyond.

If you're someone who loves creating great employee experiences, enjoys solving problems, thrives on organization, and gets excited about building efficient processes, we'd love to meet you.

This is a 100% remote role with some travel for company and team offsites, and must be based in the US (eastern time zone). No sponsorship or relocation is offered for this position. The target salary range for this role is $85-100k per year, depending on experience, skills, and location.

• Serve as a primary point of contact for day-to-day employee questions across North America.
• Conduct employee 1:1 check-ins to gather feedback and improve the overall employee experience.
• Coordinate life event recognition, employee appreciation, holiday gifts, and engagement initiatives.
• Support employee engagement programs.
• Escalate employee relations, policy, and compliance matters as appropriate.

HR Operations

• Coordinate onboarding for new hires in HiBob and Rippling.
• Maintain employee records and ensure HR system accuracy and data integrity.
• Execute promotions, organizational changes, employee lifecycle updates, and system maintenance.
• Support annual merit review administration.
• Maintain HR documentation, workflows, and operational processes.

Benefits Administration

• Administer employee benefits programs across the U.S. and Canada, including health benefits, retirement plans, wellness offerings, and employee perks.
• Manage leave and PTO administration in partnership with internal stakeholders.
• Serve as the primary contact for employee benefit questions.
• Partner with vendors to maintain and enhance employee benefit offerings.

• Coordinate Working from Abroad requests.
• Manage office reimbursement programs.
• Coordinate team remote happy hours, in-person workdays, and employee offsite logistics.
• Manage CPA Renewals and People Operations budget tracking.
• Administer Navan and other People Operations vendors.
• Support the rollout of new employee programs and benefits.

• Continuously identify opportunities to improve, automate, and scale People Operations processes.
• Partner with internal teams to improve efficiency and the employee experience.
• Maintain clean, organized, and reliable HR systems.

• 2+ years of experience in Human Resources, People Operations, or a related field, preferably in a startup environment.
• Experience supporting employee lifecycle processes in a fast-paced environment.
• Experience administering employee benefits and HR programs.
• Experience working with HRIS platforms such as HiBob, Rippling, Workday, BambooHR, or similar systems.
• Strong organizational skills with exceptional attention to detail.
• Outstanding customer service and communication skills.
• Ability to manage multiple priorities while maintaining accuracy and responsiveness.
• Experience supporting remote and distributed teams is preferred.

Success in this role:

Success in this position will be measured by:

• Delivering a best-in-class employee experience.
• Accurate and timely execution of employee lifecycle processes.
• High-quality HRIS data integrity and system administration.
• Smooth execution of onboarding, promotions, and merit cycles.
• Effective administration of benefits and employee programs.
• Continuous improvement of People Operations processes.
• Building trusted relationships with employees across North America.

In this role, you will:

• Own the employee life cycle (onboarding through offboarding) for your assigned department. You’ll meet every employee regularly, offer coaching to managers, and provide proactive advice and feedback.
• Advise and collaborate with your department’s executives (team leads through C-level). Foster close knowledge of their teams and provide coaching and training where needed, always ensuring employee and business objectives are aligned.
• Collaborate closely with our broader HR team on company processes for your department and annual HR processes for the company (performance reviews, salary cycles, etc).
• Act as the face of the company and primary touchpoint for employees in your department, and represent the voice of the employees to leadership and the HR team.
• Take on various projects related to employee experience, people operations, and company structure in close collaboration with the Chief of Staff, Americas.

Requirements:

• 2-4 years of experience in a people-facing HR function (HR generalist, employee experience, employee relations, or similar).
• Strong communication skills and the ability to earn and keep trust at all levels. You will need to represent the company and the employees, and at all times work to align these parties.
• Ability to thrive in an environment where every day is different, priorities are constantly shifting, and ‘organized chaos’ abounds. Ability to handle everything that arises with professionalism and discretion.
• Preference for candidates experienced with working with multi-cultural teams with different backgrounds and across time zones in hypergrowth environments.
• Candidates must be willing and able to meet with the team a few times a year in NYC. All candidates will be expected to attend company off-sites throughout the year.