Full-Time

Head of People Operations

Skylight

Skylight

201-500 employees

Digital consultancy for government service delivery

Compensation Overview

$170k - $240k/yr

+ Stock options + Annual performance bonus + Spot bonuses + Annual salary increase

No H1B Sponsorship

Remote in USA

Remote

Remote within the United States.

Category
People & HR (1)
Required Skills
Human Resources Information System (HRIS)
Data Analysis

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Requirements
  • 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
  • Passionately 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
  • Experience with Rippling or a comparable HRIS
  • Experience in a government contracting, consulting, or professional services environment
Responsibilities
  • 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
  • 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
  • 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
  • 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
Desired Qualifications
  • Experience with Rippling or a comparable HRIS
  • Experience in a government contracting, consulting, or professional services environment

Skylight is a digital consultancy that helps government agencies improve public services by combining design and technology. It works by offering services that blend user-centered design with technology implementation, helping agencies plan, build, and enhance digital services that citizens interact with. The company differentiates itself by focusing specifically on the public sector and partnering with government clients to deliver practical, service-oriented solutions rather than generic tech products. Skylight’s goal is to make public services easier to use, more efficient, and more accessible for citizens.

Company Size

201-500

Company Stage

N/A

Total Funding

N/A

Headquarters

North Port, Florida

Founded

2017

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Simplify Jobs

Simplify's Take

What believers are saying

  • Wired recognition and millions of families confirm strong product-market fit.
  • Profitable operations enable accelerated expansion in family tech.
  • Founders like Michael Segal drive toward $1B+ business.

What critics are saying

  • Amazon Echo Show's 10x larger base erodes Skylight's premium margins by Q3 2026.
  • Google Calendar's 500M users lock in families against Skylight switching.
  • Apple HomeHub Family launch destroys Skylight Frame's value in 12-24 months.

What makes Skylight unique

  • Skylight Calendar Max offers 27-inch touchscreen focused solely on family scheduling.
  • Seamless syncs with Google, Apple, Outlook, Yahoo, and Cozi calendars.
  • Bootstrapped to $350M+ revenue without external funding.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

Health Savings Account/Flexible Spending Account

401(k) Company Match

Unlimited Paid Time Off

Paid Vacation

Paid Sick Leave

Paid Holidays

Family Planning Benefits

Fertility Treatment Support

Professional Development Budget

Conference Attendance Budget

Wellness Program

Mental Health Support

Phone/Internet Stipend

Home Office Stipend

Stock Options

Growth & Insights

Headcount

6 month growth

23%

1 year growth

23%

2 year growth

23%