Remote Second Jobs in Silver Spring, MD (NOW HIRING)

Second Front Systems (2F) is seeking an IT Engineer to help build, automate, and scale the internal technology ecosystem that powers our mission. As a fast-growing defense technology company operating at the intersection of national security and commercial innovation, we rely on secure, reliable, and efficient internal systems to enable our employees to deliver mission-critical capabilities to our government customers.

As an IT Engineer, you will own and evolve the identity, endpoint, and business systems that support our remote-first workforce. You'll partner closely with Security, Engineering, and People Operations to deliver a seamless employee technology experience while ensuring our internal infrastructure remains secure, compliant, and scalable. This role is ideal for engineers who enjoy automating repetitive work, solving complex technical challenges, and building systems that enable organizational growth.

Beyond day-to-day operations, you'll help shape the future of IT at 2F by driving automation, improving operational processes, and implementing scalable solutions that reduce manual effort and strengthen security across the organization.

Note: This position is open to U.S.-based candidates and is fully remote, with occasional travel for company offsites and team events. Candidates must reside in one of our approved hiring hubs:

• DC/Maryland/Virginia

• Raleigh/Durham/Chapel Hill, NC

• Denver/Colorado Springs, CO

• Dallas/Fort Worth, TX

• Own identity and access management across core enterprise platforms, including Okta and Google Workspace, administering user lifecycle management, Single Sign-On (SSO), Multi-Factor Authentication (MFA), and role-based access controls.

• Lead endpoint management for company devices, primarily macOS systems managed through Jamf, developing secure endpoint baselines, software deployment workflows, and lifecycle management processes.

• Design and build automation using APIs and scripting languages such as Python, Bash, or PowerShell to streamline IT operations, eliminate repetitive tasks, and improve operational efficiency.

• Administer and support business-critical SaaS applications and collaboration platforms, ensuring secure, reliable, and scalable services that enable employees to work effectively.

• Partner closely with Security to support access reviews, vulnerability remediation, asset management, and compliance initiatives across frameworks including FedRAMP, SOC 2, ISO 27001, and CMMC.

• Serve as the senior escalation point for complex employee technology issues, major incidents, and advanced troubleshooting across identity, endpoint, and SaaS platforms.

• Continuously improve IT operations through process optimization, documentation, self-service capabilities, and scalable infrastructure that supports company growth.

• Collaborate across Engineering, Security, and People Operations to ensure internal technology solutions align with business needs while maintaining a secure and exceptional employee experience.

• 3–5+ years of experience in IT Engineering, Systems Administration, Enterprise IT, or a related technical discipline supporting cloud-first organizations.

• Hands-on experience administering identity platforms such as Okta and Google Workspace, with strong knowledge of identity lifecycle management, authentication, and enterprise access controls.

• Experience managing Apple device fleets using Jamf, including device provisioning, endpoint security, software deployment, and lifecycle management.

• Proficiency developing automation through scripting languages such as Python, Bash, or PowerShell, along with experience leveraging APIs and workflow automation tools.

• Strong understanding of SaaS administration, endpoint management, enterprise productivity platforms, and modern cloud-based IT infrastructure.

• Excellent troubleshooting and problem-solving skills with experience supporting distributed, remote-first workforces in fast-paced environments.

• Strong written and verbal communication skills with the ability to translate technical concepts for both technical and non-technical stakeholders.

• A continuous improvement mindset with a passion for automation, operational excellence, and building scalable internal technology solutions.

• Experience working in high-growth startups or rapidly scaling technology organizations.

• Familiarity with security and compliance frameworks such as FedRAMP, SOC 2, ISO 27001, and CMMC.

• Experience supporting remote-first organizations and designing employee technology experiences that scale effectively.

• Relevant certifications such as Okta Certified Professional, Jamf Certified Tech, Google Workspace Administrator, Security+, or comparable enterprise IT certifications.

• Experience partnering closely with Security teams to strengthen organizational security posture through automation, identity governance, and endpoint management.

The base salary for this position will fall between $95,000-110,000 Your ultimate compensation will be determined by professional background, technical proficiency, seniority, and regional cost factors. Furthermore, this opportunity includes potential eligibility for equity awards and discretionary bonuses, rounding out a comprehensive total rewards offering.

• Viewing obstacles as opportunities for growth

• Having a bias toward action and tangible, measurable results

• Striving to be both compassionate and direct with your feedback

• Being team-oriented and inclusive with your action

This role is a full time position. 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

• Additional benefit perks (One Medical membership, mental health resources and family planning assistance)

• Equity incentive plan

• Tech + office supplies stipend

• Annual professional development stipend

• Flexible paid time off + federal holidays off

• Parental leave

• Work virtually, near one of our hub locations

• Referral Bonus

Visit our careers page to learn more.

Second Front Systems (2F) is a public-benefit software company powering software for the free world. We eliminate the friction that slows innovation, enabling faster, more secure development and deployment of software across government and regulated networks. Built by national security veterans and backed by top-tier venture capital, our platform is trusted by the world’s leading organizations to cut deployment timelines from years to weeks. We move fast, solve hard problems, and deliver trusted capabilities where they’re needed most. Our work strengthens global security and gives the United States and its allies a lasting competitive advantage. Learn more at secondfront.com.

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.

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.

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.

Compensation Range: $95K - $110K