---
title: 'Head of People Operations at Skylight'
canonical: 'https://feeny.ai/job/head-of-people-operations-skylight-united-states-9zcjxz1hxyqe'
type: 'job'
last_seen: '2026-10-15'
---

# Head of People Operations at Skylight

- **Company:** Skylight
- **Location:** United States
- **Posted:** 2026-07-15
- **Last confirmed live:** 2026-10-15
- **Apply:** https://job-boards.greenhouse.io/skylighthq/jobs/4715704005

## 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 our Head of People Operations, you’ll be responsible for leading people operations across the company so we can continue to attract, empower, and retain amazing public interest technologists. Your work will be central to improving and scaling our ability to make a genuine difference in the world. Our Head of People Operations must have proven experience navigating the evolving legal, regulatory, and social landscapes while preserving organizational values and maintaining trusted relationships with employees, leaders, customers, and government stakeholders.

## What you’ll do

Talent acquisition

- Manage the talent life cycle, from workforce planning through onboarding, as part of the broader employee life cycle
- Provide leadership to the Head of Recruiting, who reports to this role, and grow the talent function over time
- Understand the current and future talent needs of the organization, and build and maintain a strategic talent pipeline
- Manage the onboarding process

HR

- Ensure awareness of and compliance with relevant labor laws, and lead employee relations, including sensitive and legal matters
- Perform benchmark research on compensation and benefits, and partner on HR functions such as payroll
- Manage and optimize our HRIS (Rippling)
- Create organizational charts and define each position’s responsibilities
- Manage the offboarding process

People & culture

- Own company-wide employee engagement: design and run engagement programs that reach across business units
- Manage our performance management system (e.g., individual performance planning, performance evaluation, internal promotions, continuous feedback)
- Support the development and ongoing improvement of a professional capability framework for describing and measuring how to progress and be successful in various roles at Skylight
- Discuss career-pathing options with high-potential employees and their team leaders
- Organize and oversee individual and team training programs (both internal and external)
- Design programs that build culture, drive engagement, and retain great people as we scale
- Create and implement succession plans

Across all three pillars

- Partner closely with business unit leaders and the executive team to align people strategy with the needs of the business
- Build fair, consistent people practices that reach a broad range of talent pools, reduce bias in how we evaluate candidates, and partner with organizations that widen our candidate reach
- Implement data-driven approaches to continually improving our people operations and talent outcomes
- Understand and drive the adoption of emerging best practices related to people operations

## What we're looking for

## Minimum qualifications

- Experience as a people operations leader or similar role
- Experience scaling people operations in a fast-growing organization
- Demonstrated experience building high-performing, mission-driven workplace cultures where employees feel respected, supported, and empowered to do their best work
- Sound judgment balancing transparency and visibility with confidentiality, privacy, and risk
- Experience recruiting design and technology professionals, such as product managers, product designers, user researchers, content strategists, software engineers, and DevOps engineers
- Experience working with remote teams
- Awareness of relevant labor laws and how to comply with them
- Ability to operate at strategic and tactical levels
- Excellent interpersonal, motivational, and relationship management skills
- Organized, detail-oriented, and quality-minded
- Superior written and oral communication skills
- Strong data and analytical skills
- Comfortable navigating Human Resources Information Systems, Applicant Tracking Systems, and tools that support performance management and other HR functions
- 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

Don’t meet 100% of the criteria but think you can do the job? We’d love to chat anyway! We’re on a mission to build diverse teams, and studies have shown that women and marginalized folks are less likely to apply to jobs if they don’t check every box.

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.

Care package

Salary

The salary range for this position is $170,000 to $240,000, based on experience and qualifications.

## Benefits

Your well-being is important to us, so we focus on supporting you in a variety of ways:

- 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](https://skylight.digital/careers/join/) to learn more about how our interview process works.
- Check out our [Career Pathways framework](https://skylight.digital/careers/career-pathways/) to learn more about the different roles within Skylight and the skills needed to do them.
- If you’d like to request reasonable accommodations during the application or interviewing process, please contact our recruiting team at recruiting@skylight.digital.

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.

## About Skylight

## Company Overview
- **One-liner**: Skylight is a digital consultancy that helps government agencies deliver better public services through human-centered design, lean-agile engineering, and digital transformation.
- **Entity Type**: Private (startup stage; offers stock options)
- **Headquarters**: Sarasota, Florida, USA (distributed/remote team across 34 states)
- **Founded**: June 2017
- **Founders**: Chris Cairns (President, co-founder of 18F and Technology Transformation Services)

## Core Business
- **Primary industry/industries**: Digital government consulting; public sector digital transformation
- **Target customers**: U.S. federal, state, and local government agencies (e.g., Veterans Affairs, immigration services)
- **Mission or purpose statement**: “Make government work in a digital world” – helping agencies become digital-first through culture change, modern practices, and empowered talent.

## Products & Services
Skylight offers professional services, not packaged products. Key service areas:
- **Digital Strategy & Transformation**: Roadmaps, operating model design, and organizational change management.
- **Human-Centered Design & Research**: User research, service design, and accessible interface design.
- **Lean-Agile Engineering**: Custom software development, DevOps, cloud migration, and modern infrastructure.
- **Data Science & Engineering**: Data pipelines, analytics, and machine learning for public-sector use cases.
- **Security & Compliance**: Security engineering, FedRAMP readiness, and zero-trust architecture.
- **Procurement & Acquisition**: Helping agencies buy digital services effectively using modern contracting methods.

## Market Standing
- **Valuation/Market Cap**: Not publicly available
- **Key Metric**: Team size of 164 people (as of latest update); no public revenue or funding data
- **Notable Investors/Partners**: Co-founded the **Digital Services Coalition**; no external investors disclosed (appears bootstrapped)
- **Growth Signals**: Growing headcount (164 people across 34 states), expanding client base to include Canadian government (Ottawa), active hiring for multiple senior/staff roles

## Competitive Advantages
- **Deep government DNA**: Leadership and many team members came from 18F, U.S. Digital Service, and Presidential Innovation Fellows – giving them insider knowledge of how government works.
- **Culture-first approach**: Openly shares knowledge, treats every interaction as a teaching opportunity, and prioritizes culture change as a core part of transformation.
- **Distributed & remote-native**: Built as a remote-first company from the start, allowing them to attract top talent nationwide.
- **Public-service mission**: Employees are driven by impact, not profit – creating strong alignment with government clients.

## Strategic Focus
- **Scaling digital mastery**: Helping agencies institutionalize modern practices (human-centered design, lean-agile) rather than just delivering projects.
- **Expanding into defense & security**: Actively hiring a Vice President of Defense & Security, indicating a push into national security clients.
- **Building the talent pipeline**: Offering paid internships and apprenticeships to grow the next generation of civic tech practitioners.

## Why Work Here
- **Mission-driven work**: Directly improve public services for veterans, immigrants, and millions of other citizens.
- **Remote-friendly & flexible**: Distributed team across 34 states; decide when, where, and how to work.
- **Competitive compensation**: Salary, stock options (stake in company), performance rewards, referral bonuses.
- **Benefits**: 401(k) match up to 10% of salary; up to $2,000/year professional development budget; up to 12 weeks paid parental leave; medical/dental/vision with significant premium coverage; life insurance; HSA/FSA.
- **Time off**: Flexible PTO (≈25 days/year) plus 11 paid federal holidays.
- **Tech & swag**: Annual tech budget up to $750; $100 swag budget.
- **Culture**: Strong emphasis on growth mindset, inclusivity, and continuous improvement; code of conduct; community involvement (charitable donation match up to $500/year).
- **Hiring process**: All interviews via video; focuses on getting to know you, not trick questions; accommodations available.

## Sources
1. [skylight.digital - Home](https://skylight.digital/)
2. [skylight.digital - Join Us](https://skylight.digital/careers/join/)
3. [skylight.digital - Team](https://skylight.digital/company/about/)
4. [Greenhouse - Jobs at Skylight](https://job-boards.greenhouse.io/skylighthq)

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