Chief of Staff

Summary

Join Second Front Systems (2F) as their Chief of Staff and become a pivotal part of a mission-driven team at the intersection of cutting-edge technology and national security. This role offers the chance to shape the future of a company redefining software delivery and security in the defense sector. As Chief of Staff, you will partner with the President/Chief Legal Officer, managing strategic initiatives, operations, internal communications, legal and compliance coordination, and cross-functional execution. You will drive operational clarity, strategic focus, and effective leadership across the organization. This position requires U.S. citizenship due to government contract requirements. The role involves translating vision into actionable plans, facilitating communication, managing priorities for leadership meetings, and driving follow-through on cross-functional initiatives. You will also serve as a point of contact for stakeholders and support legal and compliance processes.

Requirements

• Ability to synthesize complex information and communicate clearly across stakeholders
• Strong organizational skills and a bias toward action—able to manage multiple priorities with minimal oversight
• High emotional intelligence and the ability to work with executive discretion and confidentiality
• A strategic mindset with exceptional attention to detail and follow-through
• Strong writing, presentation, and analytical skills
• Strength of character and willingness to go the extra mile and push through obstacles when necessary
• Experience in…Getting the job done
• Supporting senior executives in a Chief of Staff, strategy, ops, or project management capacity
• Managing cross-functional initiatives in a fast-paced, high-growth startup or government/defense tech environment
• Handling confidential or sensitive information with discretion
• Navigating high-stakes internal and external stakeholder relationships

Responsibilities

• Act as a force multiplier for the President/CLO, driving operational clarity and strategic focus across the organization
• Serve as a strategic advisor and sounding board to the President/CLO, helping translate vision into actionable plans
• Coordinate and support the execution of key operational and strategic initiatives
• Facilitate communication and alignment across leadership and internal teams
• Manage priorities, agendas, and prep for leadership meetings, board updates, and strategic planning sessions
• Drive follow-through on cross-functional initiatives by owning project plans, tracking milestones, and removing roadblocks
• Serve as a point of contact for high-priority internal and external stakeholders
• Support legal, compliance and governance processes (legal experience not required.)
• Draft executive communications, presentations, and summaries to ensure crisp and effective messaging
• Help manage and triage incoming requests to the President/CLO, ensuring strategic focus is maintained
• Continuously identify process improvements to increase effectiveness and operational tempo

Preferred Qualifications

• 5–8 years of experience in operations, strategic initiatives, or legal/business support roles
• Previous experience in a venture-backed startup or in the national security sector
• Familiarity with legal operations, government contracting, or SaaS compliance frameworks
• Strong project management background (e.g., PMP, Agile practices, or similar.)
• Have a strong interest in matters of national security

Benefits

• Competitive Salary
• 100% Healthcare, vision and dental coverage
• 401(k) + 3% company contribution
• Wellness perks (Fitness classes, mental health resources)
• Equity incentive plan
• Tech + office supplies stipend
• Annual professional development stipend
• Flexible paid time off + federal holidays off
• Parental leave
• Work from anywhere
• Referral Bonus