---
title: 'Vice President of Defense & Security at Skylight'
canonical: 'https://feeny.ai/job/vice-president-of-defense-security-skylight-united-states-6aac443akrjh'
type: 'job'
last_seen: '2026-09-10'
---

# Vice President of Defense & Security at Skylight

- **Company:** Skylight
- **Location:** United States
- **Work type:** remote
- **Posted:** 2026-02-07
- **Last confirmed live:** 2026-09-10
- **Apply:** https://job-boards.greenhouse.io/skylighthq/jobs/4654607005

## 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 the Vice President (VP) of Defense & Security, you’ll own the overall success of Skylight’s defense & security business — including full accountability for profit and loss (P&L), strategic growth, and exceptional client outcomes. This portfolio includes U.S. Department of Defense (DoD) components and security-mission agencies, for example the Department of Justice (DOJ) and the Department of Homeland Security (DHS).

## What you’ll do

- Own and expand Skylight’s portfolio of work with defense and security customers, managing it as an independent business.
- Research and interpret key market drivers (such as policy shifts, mission priorities, funding patterns, and evolving threat landscapes), and proactively understand each defense and security customer’s goals, challenges, and requirements
- Translate market insights and customer feedback into innovative or enhanced service offerings, aligned with Skylight’s strategy and core capabilities
- Build strategic relationships with government stakeholders, mission leadership (military and civilian), change agents, and vendor partners to identify and pursue new business opportunities
- Lead and oversee bid & proposal processes to successfully secure client engagements
- Transform each client’s objectives and constraints into customized engagement strategies, delivering unique experiences and impactful results efficiently
- Assemble and manage multi-disciplinary teams — leveraging talent sourcing and subcontracting with vendor partners — to ensure successful client outcomes
- Provide transparent oversight and ongoing visibility into the status, health, and effectiveness of each client engagement
- Facilitate open retrospectives with clients and Skylight teams to assess effectiveness, identify improvement areas, and implement actionable changes
- Step in with hands-on client delivery support whenever necessary to maintain high-quality outcomes
- Oversee and support core operational functions, including human resource management, to enable team success and organizational effectiveness

## What we're looking for

## Minimum qualifications

- Experience in defense, homeland security, or justice mission environments
- Ability to manage a multi-million-dollar profit & loss business, including multiple client engagements with multiple subcontractors
- Ability to sustain and grow a professional services business through business development, opportunity capture, and bid & proposal
- Strong understanding of how a professional services and government contracting business works
- Startup mentality, including a high degree of entrepreneurialism and resourcefulness
- Excellent general management and leadership skills
- Outstanding organizational skills, including attention to detail
- Excellent people management skills
- Experience building and managing high-performing teams
- Relentless commitment to diversity, equity, and inclusion
- Collaborative, supportive leadership style
- Excellent interpersonal and problem-solving skills
- Strong business acumen
- Superb written and oral communication skills
- Relentless commitment to excellence and quality in everything we do
- Strong understanding of business functions such as people ops, finance, marketing, business development, etc.
- Ability to collect, analyze, and derive actionable insights from financial, operational, and performance data
- Ability to serve as a coach/mentor to other leaders and managers
- Ability to work successfully within a professional services environment (e.g., can communicate effectively with clients)
- Passionate about creating better public outcomes through great government services
- A mindset and work approach that aligns with [our core values](https://skylight.digital/company/values/)
- Ability to travel for work from time to time

Nice-to-have qualifications

- Prior experience working in the civic tech space
- Experience working in a remote-team environment

Don’t meet every qualification but think you can do the job? We’d still love to hear from you. If you’re excited about the role, apply. We consider candidates with a range of backgrounds and experiences.

Other requirements

- All work must be conducted within the U.S., excluding U.S. territories. Some federal contracts require U.S. citizenship to be eligible for employment.
- 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 complete a company background check successfully.
- Some of our available roles are on federal contracts that require a degree or additional years of experience as a substitute.

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 between $210,000 and $270,000, 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
- Flexible paid-time-off policy (generally around 25 days per year), plus 11 paid federal holidays
- 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
- Company performance and growth 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 are an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, national origin, sex, religion, age, disability, veteran status, or any other category protected by applicable law.

## 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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