Chief of Staff to the President / Chief Legal Officer

ABOUT THE ROLE

Second Front Systems (2F) is seeking an ambitious, strong, and hard working Chief of Staff to the President/CLO to join our mission-driven team. We are a dynamic, fast-growing entrepreneurial company at the intersection of cutting-edge technology and national security, committed to delivering transformative solutions that empower our nation’s defenders. This is an opportunity to play a pivotal role in shaping the future of a company that is redefining the way software is delivered and secured in the defense sector.

At 2F, we thrive on innovation and purpose, combining a startup’s agility with a clear mission to support national security. You will be at the forefront of driving the strategic alignment, operational efficiency, and execution support behind the deployment and scaling of our 2F Suite of Products including our revolutionary Game Warden platform—an industry-leading tool that is accelerating the secure adoption of mission-critical SaaS solutions for the U.S. government. If you’re ready to contribute to a team that values ingenuity, collaboration, and impact, we want to hear from you.

As Chief of Staff, you will serve as a trusted partner and right hand to the President/Chief Legal Officer helping manage and prioritize strategic initiatives, operations, internal communications, legal and compliance coordination, and cross-functional execution. You’ll play a critical role in enabling effective leadership, facilitating cross-team alignment, and ensuring the leadership office operates with clarity and impact.

Note: This position requires U.S. citizenship due to government contract requirements.

• You’ll 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.

• 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.

• 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.

• 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.

Perks & Benefits

This role is full time.  As a public benefit corporation, we’re a team of purpose-driven trailblazers transforming the future of U.S. national security. We hire the best to do their best and, as such, we are committed to providing the perks and benefits you need to be successful—both in- and outside the workplace.

We offer you:

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

Visit our careers page to learn more.

Please note that all official communications will come from @secondfront.com email addresses. If you are contacted by anyone claiming to represent Second Front and are unsure of their authenticity, please do not provide any personal/financial information and contact us immediately at security@secondfront.com.

If you believe you are the target of a scam in the US, please report it to the Federal Trade Commission at: https://reportfraud.ftc.gov/#/. In Europe, please contact the European Anti-Fraud Office at: https://anti-fraud.ec.europa.eu/olaf-and-you/report-fraud_en

WHO WE ARE

At Second Front Systems (2F), we equip defense and national security professionals for long-term, continuous competition for access to emerging technologies. Founded by two former U.S. Marines with firsthand experience of the dangers outdated technology poses in combat, our team is dedicated to fast-tracking government access to disruptive, commercially-proven technology for U.S. national security missions. 

Our Game Warden product, a fully managed and compliant DevSecOps platform, accelerates the process for accrediting software as a service (SaaS) applications for government use.

Learn how 2F can help you make an impact on national security missions at www.secondfront.com

ONE LAST THING…

We are an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other characteristic protected by law.

Are you ready to join our team?

To apply, click the “Apply for This Job” button at the top or bottom of this page and complete the application form.

This position will remain open until filled, and applications will be reviewed on a rolling basis.

STATE NOTICES

Colorado:

In accordance with Colorado law, applicants may redact their date of birth, dates of attendance, and dates of graduation from any uploaded documents.

Maryland:

UNDER MARYLAND LAW, AN EMPLOYER MAY NOT REQUIRE OR DEMAND, AS A CONDITION OF EMPLOYMENT, PROSPECTIVE EMPLOYMENT, OR CONTINUED EMPLOYMENT, THAT AN INDIVIDUAL SUBMIT TO OR TAKE A POLYGRAPH EXAMINATION OR SIMILAR TEST. AN EMPLOYER WHO VIOLATES THIS LAW IS GUILTY OF A MISDEMEANOR AND SUBJECT TO A FINE NOT EXCEEDING $100.