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Skylight

Digital consultancy for government service delivery

Vice President of Defense & Security

Full-Time
$210k - $270k/yr
Expert
Remote in USA
Remote
Business & Strategy
No H1B Sponsorship
US Citizenship Required

About the job

Requirements
  • Experience in defense, homeland security, or justice mission environments.
  • Ability to manage a multi-million-dollar profit and 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 and proposal processes.
  • Strong understanding of professional services and government contracting businesses.
  • Startup mentality, including entrepreneurialism and resourcefulness.
  • General management and leadership skills.
  • Organizational skills, including attention to detail.
  • People management skills.
  • Experience building and managing high-performing teams.
  • Commitment to diversity, equity, and inclusion.
  • Collaborative and supportive leadership style.
  • Interpersonal and problem-solving skills.
  • Business acumen.
  • Written and oral communication skills.
  • Commitment to excellence and quality.
  • Understanding of business functions such as people operations, finance, marketing, and business development.
  • Ability to collect, analyze, and derive actionable insights from financial, operational, and performance data.
  • Ability to coach and mentor other leaders and managers.
  • Ability to work successfully within a professional services environment and communicate effectively with clients.
  • Ability to travel for work from time to time.
  • All work must be conducted within the United States, excluding U.S. territories.
  • Legal authorization to work in the United States now and in the future without sponsorship.
Responsibilities
  • Own and expand Skylight’s portfolio of work with defense and security customers, managing it as an independent business.
  • Research and interpret market drivers such as policy shifts, mission priorities, funding patterns, and evolving threat landscapes, and understand customers’ 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, change agents, and vendor partners to identify and pursue new business opportunities.
  • Lead and oversee bid and proposal processes to secure client engagements.
  • Transform client objectives and constraints into customized engagement strategies and deliver efficient, impactful results.
  • Assemble and manage multidisciplinary teams, using 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 retrospectives with clients and Skylight teams to assess effectiveness, identify improvement areas, and implement actionable changes.
  • Provide hands-on client delivery support when necessary to maintain high-quality outcomes.
  • Oversee and support core operational functions, including human resource management, to enable team success and organizational effectiveness.
Desired Qualifications
  • Prior experience working in the civic technology space.
  • Experience working in a remote-team environment.

About the company

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

Grant

Total Funding

$1.9M

Headquarters

North Port, Florida

Founded

2017

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Simplify's Take

What believers are saying

  • September 30, 2026 credit expansion funds new products and broader distribution.
  • Buddy sold out within a week, signaling strong demand for kid-focused hardware.
  • Skylight said business doubled in 2026 and reached 12 million customers.

What critics are saying

  • Amazon, Apple, and Google commoditize shared-family scheduling inside household devices quickly.
  • Credit facility expansion to $75 million adds repayment pressure if product launches stall.
  • Skylight Assistant relies on sticky SMS habits; churn kills subscription economics within months.

What makes Skylight unique

  • Skylight bundles calendars, frames, and kids’ routines into one family OS.
  • Skylight Assistant runs over SMS, avoiding app fatigue for busy households.
  • Bootstrapped since 2014, Skylight reinvests profits instead of chasing VC growth.

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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

Growth & Insights

Headcount

6 month growth

24%

1 year growth

27%

2 year growth

27%