Chief of Staff, Second Front Systems
To the President / Chief Legal Officer
$160-176k
+ Equity
More information about location
Security software solutions company
Open for applications
Security software solutions company
101-200 employees
Open for applications
$160-176k
+ Equity
More information about location
101-200 employees
Company mission
To accelerate the delivery of emerging technologies to U.S. and Allied warfighters.
Role
Who you are
- If you’re ready to contribute to a team that values ingenuity, collaboration, and impact, we want to hear from you
- 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
What the job involves
- Second Front Systems (2F) is seeking an ambitious, strong, and hard working Chief of Staff 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
- 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
- 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
Our take
It goes without saying that national security is of extremely high importance and billions of relevant currencies are fuelled into achieving the highest standards each year. Second Front Systems fast-tracks government access to disruptive, commercially-proven, SaaS applications for national security missions.
Founded in 2014 by two former U.S. Marines, they used experience of outdated technology and systems to power the company's national security mission. Since its founding, Second Front has developed a DevSecOps platform and several AWS GovCloud solutions.
2023-24 funding rounds mean the company can now look to expand into the UK market and position its DevSecOps platform Game Warden as a software bridge between the two nations. The current operations and software used by the two countries are not matched and this ironing out could be transformational for the progress of joint security. The company is described as a market leader and it’s clear it is making huge progress in sectors of great importance.
Steph
Company Specialist at Welcome to the Jungle
Insights
61% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Sep 2024
$70m
SERIES C
Nov 2023
$40m
SERIES B
Total funding: $152.1m
Company benefits
- Health - Receive medical, dental, and vision coverage with a significant company contribution to premiums for both the employee and family members. Additionally, wellness services are provided for physical exercise through ClassPass and mental health through Talkspace.
- 401k - We offer a 401k program with a range of high-quality investment options. Your eligibility begins after 90 days and the company makes an automatic 3% monthly contribution regardless of how much you contribute from your salary.
- Health - Receive medical, dental, and vision coverage with a significant company contribution to premiums for both the employee and family members. Additionally, wellness services are provided for physical exercise through ClassPass and mental health through Talkspace.
- Equity - Gain ownership in the company as you work to grow it alongside your teammates with our equity incentive plan managed through Carta. As the company’s success grows, yours will too
- Additional Benefits (Company Funded) - Life Insurance Short-Term Disability Long-Term Disability
- Work From Anywhere - We operate as a remote-first and collaboration-driven company with operations that span the globe. We ensure you have access to the best tools to do your job from home and provide an annual office stipend.
- Flexible PTO - We provide flexible time off, recognise 11 federal holidays, and offer 12 weeks of parental leave.
- Professional Development - We value your drive to grow and provide an annual stipend for self-directed professional development.
Company HQ
Trolley Square, Wilmington, DE
Leadership
Tyler Sweatt
(CEO (not founder))Currently Partner at the Silicon Valley Defense Group, Technical Advisor at Pallas Advisors, Advisory Board Member at Calypso AI and Advisor at GovCity.
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