Senior Engagement Manager

Summary

Join Skylight's cross-functional team supporting a high-impact Department of Defense (DoD) digital modernization effort. This initiative focuses on strengthening product leadership, human-centered design, and systems engineering across multiple agile product lines. As a member, you'll help stand up a team that brings unbiased product strategy, scalable service design practices, and rigorous systems thinking to the federal government. Your work will shape how this organization aligns its value streams to customer needs, improves enterprise architecture and planning, and builds internal capacity. Skylight's team will support multiple agile product lines and deliver measurable improvements in team alignment, efficiency, and delivery outcomes. This is a unique opportunity to help modernize how the government builds and scales software, with direct impact on national security outcomes.

Requirements

• Experience managing agile digital delivery in a consulting or professional services environment
• Ability to translate client goals into actionable strategies and build lasting relationships based on trust and impact
• Ability to grow Skylight’s business through business development activities
• Track record of fostering high-performing, collaborative teams—especially in distributed, cross-functional settings
• Familiarity with government delivery environments and the ability to ensure contractual compliance
• Strong communication skills, including the ability to mediate between technical and non-technical stakeholders
• 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
• Ability to obtain a Common Access Card (CAC), including successful completion of a DoD background investigation
• 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

Responsibilities

• Translate the client’s objectives and constraints into an engagement approach that'll deliver a unique experience and impactful results in the shortest amount of time possible
• Assemble a multi-disciplinary team of experts from a variety of backgrounds to deliver the engagement
• Manage multiple projects aimed at delivering transformation or a specific product using the appropriate methodologies (e.g., Scrum or kanban)
• Set up the team for successful delivery by removing obstacles, coaching them on how to become more collaborative and self-organizing, and enabling the work they do rather than impose how it’s done
• Conduct retrospectives with both the client and Skylight team to learn what is and isn’t working well, and formulate and implement improvement actions
• Provide management- and team-level visibility into the status and health of the engagement

Preferred Qualifications

• Ability to support capacity-building through enablement, documentation, and knowledge transfer
• Federal systems experience supporting large-scale, modular DoD systems or DevSecOps platforms
• Civic tech background. Prior involvement in the civic tech space
• Remote teamwork. Experience collaborating effectively with distributed teams
• Ability to obtain a Common Access Card (CAC), including successful completion of a DoD background investigation
• Existing or prior possession of a CAC with completed DoD background check

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