Vice President of Training Services (remote)

The Skylight
 Sarasota, FL


Skylight is at the forefront of a civic movement to reinvent how the government serves the public in a digital world.

Our talented team of designers, engineers, and more consists of former Presidential Innovation Fellows, founders of 18F, and members of the U.S. Digital Service.

We firmly believe that government success requires working closely with them to build up their internal capacity to deliver great digital services. The work is challenging, but highly rewarding: Millions of people — from veterans to immigrants — depend on government services to fulfill their needs every day.

Since launching a few 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.

Our company is organized into five main groups: Executive Office (sets and operationalizes the strategic direction of the company), Human Services (focused on clients such as the Centers for Medicare & Medicaid Services), Defense Services (focused on clients such as the U.S. Air Force), Training Services (focused on providing educational services to various government clients), and Service Excellence (focused on continually improving how we deliver client experiences and services across the company).

We’re looking for a talented executive to join our growing team and serve as Skylight’s Vice President (VP) of Training Services.


What you’ll do:

  • Manage and grow Skylight’s portfolio of work with various government agencies, as if it were an independent business
  • Research and understand the forces shaping the learning and professional development needs of government agencies
  • Translate market and customer insights into new or improved educational offerings, in alignment with Skylight’s strategy and core capabilities
  • Develop and capture business opportunities through a combination of marketing, sales funnel management, customer relationship management, vendor partnerships, and bid & proposal management
  • Oversee the planning and execution of all client engagements and student courses, including sourcing expert trainers and managing logistics
  • Oversee and provide visibility into the status, health, and performance of all client engagements and student courses
  • Gather feedback and/or conduct transparent retrospectives with clients, students, instructors, and other staff members to learn what is and isn’t working well, and formulate and implement improvement actions
  • Be willing to provide hands-on delivery support, where necessary
  • Partner closely with the VPs of Defense Services and Health Services around opportunities to improve and expand our portfolio of educational services
  • Partner closely with the VP of Service Excellence to continually improve how we deliver services to clients and students
  • Perform and support core operational functions such as human resource management

What we’re looking for:

  • Startup mentality, including a high degree of entrepreneurialism and resourcefulness
  • Ability to manage a multi-million-dollar P&L
  • Experience as an instructional designer, including multi-modal learning
  • Experience with learning management systems
  • Experience building and managing high-performing teams
  • Experience with government contracting and contract management
  • Collaborative, supporting leadership style
  • Excellent interpersonal and problem-solving skills
  • Superior written and oral communication skills
  • A mindset and work approach that aligns with our core values
  • Ability to travel (when it's safe)

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 than men to apply to jobs if they don't check every box.