Full-Time

Staff/Principal Security Engineer

Hhs

Posted on 2/23/2026

Skylight

Skylight

201-500 employees

Digital consultancy for government service delivery

Compensation Overview

$135k - $160k/yr

No H1B Sponsorship

Remote in USA

Remote

Travel to Washington, DC periodically for in-person collaboration.

US Citizenship, US Top Secret Clearance, Canada Citizenship, UK Top Secret Clearance Required

Category
IT & Security (1)
Required Skills
PowerShell
Bash
Fedramp
Python
Threat modeling
Infrastructure as Code (IaC)
Terraform
DevOps
Requirements
  • Experience identifying, prioritizing, and mitigating security risks across applications, infrastructure, and cloud environments
  • Familiarity with embedding security practices throughout product development and delivery
  • Ability to script or use automation tools (e.g., Python, Bash, PowerShell, Terraform) to implement security and compliance controls
  • Understanding of regulatory and compliance contexts such as the Federal Risk and Authorization Management Program (FedRAMP), the Federal Information Security Modernization Act (FISMA), or the Health Insurance Portability and Accountability Act (HIPAA)
  • Clear communication skills to explain risks, tradeoffs, and recommendations across technical and non-technical audiences
  • Commitment to equipping federal teams with documentation, training, and mentoring so improvements last beyond the contract
  • Ability to work effectively in a professional services environment
  • Passion for improving public outcomes through secure, resilient government services
  • A mindset and work approach that align with Skylight’s core values
Responsibilities
  • Lead threat modeling, security design reviews, and risk analyses that shape enterprise platforms and services
  • Implement remediations and automation that strengthen resilience across infrastructure, cloud environments, and applications
  • Define and evolve secure defaults and guardrails — including CI/CD templates, policy as code, and infrastructure as code (IaC) modules
  • Partner with product, design, and engineering teams to embed security throughout the delivery lifecycle
  • Establish meaningful security metrics (e.g., time-to-remediate, mean time to detect/respond, control coverage) and use them to guide decisions
  • Strengthen incident readiness through tabletop exercises, playbooks, and continuous improvement of runbooks and controls
  • Advise leadership on tradeoffs and strategies for scaling security in multi-team environments
  • Help federal teams sustain improvements by delivering training and enablement, and by leaving behind reusable resources such as templates, playbooks, and decision records
Desired Qualifications
  • Deep knowledge of identity and access management (IAM), zero-trust architectures, or continuous Authority to Operate (cATO) practices
  • Experience leading large-scale cloud modernization efforts on platforms such as Amazon Web Services (AWS) or Microsoft Azure
  • Track record of mentoring engineers and building security practices across organizations
  • Experience in civic tech, government, or other highly regulated environments
  • Experience working effectively on hybrid or distributed teams
  • Ability to spend time on-site at HHS in Washington, DC — either by being based locally or by traveling periodically for in-person collaboration

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

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

INACTIVE