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. What You'll Do 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)