People Operations Manager

Skylight; Oregon; Hybrid; USD 100,000 - 130,000; Full time

Benefits offered by this job

Medical insurance

Dental & Vision insurance

Disability & life insurance

401(k) with company match

Paid time off & holidays

Professional development allowance

Job summary

Skylight is seeking a seasoned People Operations Manager to oversee benefits and leave programs, manage the HRIS, and guide the employee lifecycle from onboarding to offboarding. You will partner with leaders to ensure compliant, scalable processes for a distributed workforce working fully remotely.

In this role, you will own vendor relationships, drive process improvements, and support employee relations with a focus on transparency, privacy, and policy accuracy.

Qualifications

• Five+ years in an HR generalist, people operations, or benefits/leave role.
• End‑to‑end benefits administration ownership, including broker management, renewals, and open enrollment.
• End‑to‑end leave administration across multiple states with policy and compliance awareness.
• Experience supporting employee relations matters, including documentation and correspondence.
• Knowledge of federal and multi‑state employment law as it applies to leave, classification, and pay practices.

Responsibilities

• Administer benefits programs end to end (medical, dental, vision, disability, life, FSA/HSA, 401(k)).
• Run annual open enrollment and coordinate with carriers and HRIS configurations.
• Administer leaves of absence across states and ensure compliant payroll adjustments.
• Oversee onboarding and offboarding end to end, including I-9/E-Verify where applicable.
• Support employee relations and provide documentation and communications as needed.
• Maintain HR policies, training, and communications to ensure compliance and clarity.

Skills

Benefits administration

Leave administration

HRIS administration

Onboarding & offboarding

Employee relations

Policy communication

Remote workforce experience

Cross‑functional collaboration

Education

PHR/SPHR/SHRM-CP/SHRM-SCP

Tools

Rippling

Job description

About Skylight

Skylight is a digital consultancy using design and technology to help government agencies deliver better public services. We're at the forefront of a civic movement to reinvent how all levels of government serve families, patients, and many others in today's digital world. If you want to play a part in driving this critical movement forward, we'd love for you to join our growing team of public interest technologists. The work we do matters.

About the job

Since launching several years ago, our team has grown rapidly. We find ourselves in an exciting position to further deepen our partnerships within the government contracting space, to continue to attract and retain amazing teammates, and to scale our capacity to make an even bigger difference in the world. Currently, our company is organized into three main groups: Executive Office (sets and operationalizes the strategic direction of the company), Federal Health & Civilian (focused on federal health and civilian missions), and Defense & Security (focused on defense, national security, and public safety missions). As Skylight's People Operations Manager, you'll report directly to the Head of People Operations and play a vital role in running the people programs our team relies on every day. In this hands-on position, you'll focus on administering benefits and leave, managing the employee life cycle from onboarding through offboarding, and keeping our people systems, records, and policies accurate and current. The work you do will have a direct impact on our ability to attract, support, and retain amazing public interest technologists.

What you'll do

Benefits and leave

• Administer our benefits programs end to end, including medical, dental, vision, disability, life, FSA, HSA, and 401(k)
• Own the working relationship with our benefits broker and carriers, including renewals, plan design discussions, and issue escalation
• Run annual open enrollment, from communications and employee education through system configuration and post-enrollment reconciliation
• Administer all leaves of absence, including parental, medical, FMLA, short-term disability, and state paid family and medical leave programs
• Maintain leave tracking and reporting so business unit leaders have the staffing visibility they need without exposing confidential detail
• Partner with Finance on payroll inputs, leave-related pay adjustments, and benefits reconciliation

Employee lifecycle

• Run onboarding end to end, including the preboarding checklist, new employee orientation, I-9 verification meetings, and E-Verify submissions, and coordinate with IT so system and equipment access is ready on day one
• Run manager onboarding for employees stepping into people-management roles
• Run offboarding end to end, including the checklist, exit surveys, and state compliant final pay and benefits steps, and confirm with IT that access is revoked and equipment is returned
• Process role, project, and reporting-line transitions, keeping employee records and timekeeping assignments aligned and routing access changes to IT
• Maintain employee data across our people systems, including address and status changes that carry tax or compliance implications

People systems and data

• Serve as the administrator for our HRIS (Rippling), covering configuration, data integrity, reporting, and integrations with our timekeeping and payroll systems
• Build and maintain automated workflows in the HRIS so routine people processes run without manual intervention
• Run HRIS and people-system implementations and migrations, including vendor coordination, data validation, go-live readiness, and post-launch stabilization

Employee relations and performance

• Support employee relations matters by conducting intake, maintaining documentation, preparing correspondence, and coordinating with the Head of People Operations and outside counsel where needed
• Support managers through performance conversations and performance improvement plans, including template preparation, documentation standards, and follow-up tracking
• Run the mechanics of our compensation and promotion cycles, including packet assembly, tracker maintenance, letter generation, and system updates

Policy, compliance, and communications

• Serve as the first point of contact for employee questions on benefits, leave, pay, and policy, through our People Operations inbox and our internal request channels
• Maintain our people policies and knowledge base, keep the policy backlog current, and flag where a policy is missing, stale, no longer compliant, or contradicted by practice
• Deploy and track mandatory compliance training, such as anti-harassment and security awareness, and follow up on non-completions
• Monitor multi-state employment compliance obligations and surface changes that affect our policies or practices
• Write and publish company-wide people communications, including benefits deadlines, policy changes, and process updates
• Maintain the SOPs, templates, and checklists behind our people workflows so the process survives any one person
• Identify manual processes worth automating and use our tools, including AI, to reduce the administrative load on the function
• Contribute to a work environment where people feel supported, informed, and treated consistently

What we're looking for

Minimum qualifications

• Five or more years of progressive experience in an HR generalist, people operations, or benefits and leave role
• Demonstrated ownership of benefits administration end to end, including broker management, renewals, and open enrollment
• Demonstrated ownership of leave administration across multiple states, including interaction between company policy, federal leave law, and state paid leave programs
• Experience supporting employee relations matters, including documentation, correspondence, and knowing when to
• Working knowledge of federal and multi-state employment law as it applies to leave, accommodation, classification, and pay practices
• Sound judgment balancing transparency and visibility with confidentiality, privacy, and risk
• Proven ability to collaborate across the business, partnering openly with leaders and teams rather than working in a silo
• Hands‑on administration of an HRIS, including reporting, configuration, workflow automation, and data integrity
• Experience running onboarding and offboarding end to end, including I-9 and E-Verify compliance
• Experience working with remote and distributed teams
• Organized, detail-oriented, and quality-minded, with the follow-through to close items rather than route them
• Superior written and oral communication skills, including the ability to explain a policy clearly to someone who is frustrated
• Comfort working without a playbook, and the instinct to write one afterward
• Passionate about creating better public outcomes through great government services
• A mindset and work approach that aligns with our core values
• Ability to travel for work from time to time

Nice-to-have qualifications

• Experience with Rippling or a comparable HRIS
• Experience in a government contracting, consulting, or professional services environment
• Experience administering benefits and leave through a company's growth from roughly 100 to 300 employees
• Experience implementing a leave management platform, a benefits administration system, or an HRIS migration
• Experience deploying and tracking mandatory compliance training across a distributed workforce
• Familiarity with government contractor compliance obligations, such as EEO reporting, affirmative action planning, or Service Contract Act requirements
• Professional certification such as PHR, SPHR, SHRM-CP, or SHRM-SCP

We consider candidates with a range of backgrounds and experiences.

Other requirements

• All work must be conducted within the U.S.
• You must be legally authorized to work in the U.S. now and in the future without sponsorship.
• As a government contractor, you may be required to obtain a public trust or security clearance.
• You may be required to successfully complete a company background check.

Position type

This is a full-time, exempt position.

Location

This is a fully remote position.

Salary

The salary range for this position is $100,000 - $130,000 based on experience and qualifications.

Benefits

• Medical insurance, dental insurance, vision insurance
• Short-term and long-term disability insurance
• Life and AD&D insurance
• Dependent care FSA, healthcare FSA, health savings account
• Dollar-for-dollar 401(k) match up to 10% of your salary with no vesting period
• Paid time off, including 20 vacation days, 11 federal holidays, and flexible sick leave
• Up to 12 weeks paid time off for all eligible new birth, adoption, or foster parents
• Performance rewards, including annual salary increase, annual performance bonus, spot bonuses, and stock options
• Business development / sales bonuses
• Referral bonuses
• Annual $2,000 allowance for professional development
• Annual $750 allowance for tech-related purchases
• Annual swag budget of $100 to display your Skylight pride with some merchandise (hoodies, hats, and more)
• Flexible, remote-friendly work environment
• An environment that empowers you to unleash your superpowers for public good

Interview tips

• Visit our join page to learn more about how our interview process works.
• Check out our Career Pathways framework to learn more about the different roles within Skylight and the skills needed to do them.

We participate in E-Verify and upon hire, will provide the federal government with your Form I-9 information to confirm that you're authorized to work in the U.S.

We're an Equal Opportunity/Affirmative Action Employer. All qualified applicants will receive consideration for employment without regard to race, color, national origin, ancestry, sex, sexual orientation, gender identity or expression, religion, age, pregnancy, disability, work-related injury, covered veteran status, political ideology, marital status, or any other factor that the law protects from employment discrimination.