Vice President Of Training Services

Skylight Sarasota , FL 34236

Posted 7 days ago

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).

Were looking for a talented executive to join our growing team and serve as Skylights Vice President (VP) of Training Services.


What youll do:

  • Manage and grow Skylights 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 Skylights 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 isnt 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 were 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)


We focus on supporting you in a variety of ways:

  • Competitive salary
  • Ownership in the company through stock options
  • 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
  • Flexible paid-time-off policy (minimum of 29 days), which covers any type of leave (such as holiday, sick, and vacation) that you need or want to take
  • Minimum of 9 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 additional stock options
  • Business development / sales bonuses
  • Annual $2,000 allowance for professional development
  • Annual $750 allowance for tech-related purchases
  • Annual swag budget of $50 to display your Skylight pride with some merchandise (hoodies, hats, and more)
  • Dollar-for-dollar charity donation matching, up to $500 per year
  • Access up to $1,000 before payday to cover emergency expenses
  • Remote-friendly work environment
  • An environment that empowers you to unleash your superpowers for public good

We participate in E-Verify and upon hire, will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S.

We're an Equal Opportunity/Affirmative Action Employer. All qualified applicants will receive consideration for employment without regard to race, color, national origin, ancestry, sex, sexual orientation, gender identity or expression, religion, age, pregnancy, disability, work-related injury, covered veteran status, political ideology, marital status, or any other factor that the law protects from employment discrimination.

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Vice President Of Training Services