Head of Compliance

Shift5 is redefining the future of onboard operational technology (OT). As a fast-growing scale-up, we specialize in cutting-edge cybersecurity, predictive maintenance, and compliance for OT systems across defense, aerospace, and rail. We are a team of passionate, innovative professionals who thrive in a collaborative environment, driven by a shared mission to revolutionize how fleets operate. By unlocking and democratizing the vast potential of onboard OT data, we help our customers’ fleets run smarter, safer, and more efficiently. Ready to be part of the next frontier in transportation and critical infrastructure? Come join us.

• Mission First Mindset: We exist to protect the service members who defend our nation and secure the critical systems that keep our economy moving.
• Relentless Innovation: We are motivated by the challenge of solving the toughest problems facing transportation and defense industries.
• Data Driven Decisions: We make decisions rooted in data. Giving our team and stakeholders a more informed perspective possible when lives and missions are on the line.

Shift5 is seeking a Head of Compliance to join our growing Product/Engineering team. In this role, your primary responsibility will be to serve as the strategic lead for all DoD compliance initiatives, ensuring our hardware and software solutions meet the rigorous standards of the Army, Navy, and Air Force. You will lead and scale a dedicated compliance function, providing direct management and mentorship to technical staff while establishing the "gold standard" for our internal compliance roadmap.

Who You Are

• A Seasoned Expert: You have navigated the complexities of large-scale federal programs and can leverage that "been there, done that" perspective to challenge our current processes and implement industry-leading best practices.
• Technically Grounded: You have a strong background in software compliance (STIGs, CDRLs) and are comfortable with automation. Bonus points if you’ve reviewed code or managed security engineers in the past.
• Adaptable & Scrappy: You understand the difference between a legacy defense giant and a fast-moving scale-up. You know how to achieve "best of the best" results without the infinite resources of a Tier 1 Prime.
• A Natural Leader: You are experienced in managing and mentoring people, specifically technical compliance and security engineering talent.

• Strategic Oversight: Own the top-level DoD compliance strategy, navigating the unique software and hardware requirements for each military branch. Build and formalize a scalable compliance governance program, including policy development, review boards, documentation standards, and audit preparation processes.
• Team Leadership: Manage and grow a compliance team responsible for documentation, control validation, and program-level coordination.
• Proactive Compliance: Establish structured compliance review gates prior to product release to ensure contractual and regulatory requirements are satisfied. Ensure appropriate technical controls are defined and implemented by engineering teams, and validate their effectiveness through structured review and audit processes. 
• Customer Engagement: Travel up to 30% to customer sites to interface with DoD stakeholders and ensure seamless delivery of compliant systems. Serve as the primary compliance representative to DoD stakeholders, auditors, and accreditation authorities.
• Cross-Functional Collaboration: Partner closely with the broader engineering team to integrate compliance into the development lifecycle. Maintain risk registers and POA&M tracking, providing executive-level reporting on compliance posture and risk burn-down across programs.

Compensation & Benefits:

• Base Salary: $180,000-$210,000
• Bonus program and equity in a fast-growing startup
• Competitive salary and stock options in a fast-growing startup
• Employer-paid medical, dental and vision coverage
• Health Savings Account with annual employer contributions
• Life Insurance
• Uncapped paid time off policy
• Flexible work & remote work policy
• Tax-deferred public transit benefits with Metro SmartBenefits (DC/MD/VA)

We are committed to building an inclusive culture of belonging that embraces the diversity of our people and represents the communities in which we work and the customers we serve. We know the happiest and highest performing teams include people with diverse perspectives and ways of solving problems. We strive to attract and retain talent from all backgrounds and create workplaces where everyone feels empowered to bring their full, authentic selves to work.

Shift5 is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sexual orientation, gender identify, national origin, disability, age, marital status, ancestry, projected veteran status, or any other protected group or class.