Remote Chief of Staff

Summary

Join our growing team of public interest technologists as Skylight's Chief of Staff and report directly to the CEO. As a strategic partner, you'll provide advice and counsel, set priorities, manage projects, and build relationships with key stakeholders.

Requirements

• 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
• Passionate about creating better public outcomes through great government services
• A mindset and work approach that aligns with our core values
• Ability to travel for work from time to time

Responsibilities

• Be a strategic partner to the CEO and other executives, including providing strategic advice and counsel, setting and managing strategic priorities
• Preparing for and following up on meetings, reviewing internal and external communications, and managing the flow of information
• Assume day-to-day responsibility for projects and tasks, including serving as the strategic lead on high-priority initiatives
• Bringing together multiple stakeholders to help drive decisions, unblocking issues affecting the performance of teams or the organization
• Making informed recommendations based on data, streamlining operations, and hiring key personnel
• Build a diverse, inclusive, equitable, and performance-oriented culture, ensuring that team members thrive and organizational outcomes are met
• Ensure executive leaders and the Board of Directors have ongoing visibility into the financial, operational, and performance health of the company
• Lead the company’s annual and cyclical strategic planning processes
• Develop and maintain cross-organizational relationships to enable leadership success
• Build and maintain trusted relationships with key customers, partners, stakeholders, vendors, and banks

Benefits

• 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
• Paid time off, including 20 vacation days, 11 federal holidays, and flexible sick leave
• 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
• Business development / sales 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)
• Dollar-for-dollar charity donation matching, up to $500 per year
• Access up to $1,000 before payday to cover emergency expenses
• Flexible, remote-friendly work environment