Senior Director of Engineering

Sr. Director of Engineering, RegScale 

RegScale is a purpose-built cyber GRC platform designed to enable the CISO to track and monitor security controls. We help organizations break out of the slow and expensive realities that plague legacy GRC tools by bridging security, risk, and compliance through controls lifecycle management. By leveraging RegScale’s Continuous Control Monitoring (CCM) instrumentation, organizations experience massive compliance process improvements like 90% faster certification times, and 60% less audit prep time. Today's expansive security and compliance requirements can only be met with a modern, CCM-based approach, and RegScale is the market leader in that space. 

Position 

Are you an engineering leader who thrives on transformation? Do you get excited when you see an opportunity to take good engineering teams and make them great? We're seeking an exceptional Senior Director of Engineering who has a proven track record of driving measurable improvements in delivery velocity, software development processes, Git Flow, code quality, and team performance. 

If you are looking for a comfortable 9 – 5 job, this isn’t it.  This is a unique opportunity for a proven leader who loves the challenge of modernizing development practices, implementing agile methodologies at scale, and building high-performing engineering cultures within a high-paced startup environment. If you have a history of coming into organizations and elevating their engineering execution—with the KPIs and success stories to prove it—we want to meet you. 

This role offers the autonomy to implement the processes, practices, and cultural changes needed to build a world-class engineering organization. You'll work closely with our Chief Product Officer and CEO to ensure our technical execution matches the strength of our product vision and market opportunity. We offer a compensation package including competitive base salary and stock options because we know that exceptional leadership at this level is transformational for the entire company. 

This position can be filled remotely and requires US Citizenship. Our team is distributed, but our central office is in Knoxville, TN and travel to this office on occasion is expected in this role. Candidates must pass a background check to be eligible for employment.  

What You'll Accomplish 

• Engineering Excellence & Delivery:
  • Lead the way to fully transition from informal current development practices to modern agile/scrum methodologies with measurable velocity improvements and a rigorous process orientation
  • Establish and drive KPIs including sprint completion rates, deployment frequency, defect escape rates, code coverage, and technical debt reduction
  • Implement code quality standards and CI/CD pipelines that enable reliable, secure, and predictable delivery
  • Monitor pipeline telemetry and outputs to continuously improve software quality, security, and performance
  • Balance driving new feature development with bug fixes, product stabilization, and strategic technical debt management 
• Team Development & Performance:
  • Build a high-performing engineering culture through coaching, mentoring, and developing talent
  • Serve as a player/coach who can help solve the hardest problems with hands on-engineering excellence while conducting knowledge transfer to the team
  • Make strategic hiring decisions to strengthen team capabilities and address skill gaps
  • Conduct weekly 1-on-1 sessions focused on growth, removing blockers, and driving accountability
  • Establish clear performance expectations and provide direct feedback that helps team members excel
  • Set annual employee goals, conduct performance reviews, and partner with HR on talent management 
• Operational Leadership:
  • Troubleshoot complex code issues and guide the team through refactoring efforts
  • Lead daily Scrum/Stand Up meetings that drive action and accountability
  • Ensure sprint activities directly support and align with the CEO and Chief Product Officer's vision and product roadmap
  • Conduct thorough code reviews of Pull Requests in GitHub, enforcing quality standards
  • Ensure comprehensive documentation is available on regscale.readme.io for customer support
  • Manage training, travel, and discretionary R&D budgets as approved/delegated by the CPO
  • Complete additional management duties as assigned by the CEO and CPO 

Candidate Requirements 

• Minimum of 7 years of progressive software engineering management experience in a technical role
• Expert-level knowledge of Agile/Scrum processes (certifications such as CSM, PSM, or SAFe a plus)
• Demonstrated experience leading agile/scrum transformations with measurable improvements in team delivery (Jira experience a plus)
• Deep experience with modern GitOps, branching strategies, CI/CD pipelines, and DevOps processes (GitHub experience a plus)
• Strong code review capabilities with ability to ensure quality across multiple programming languages
• Understanding of quality metrics, testing strategies, and architectural decisions that reduce technical debt while supporting extreme scale
• Proven ability to develop employee goals, provide constructive feedback, and address performance issues
• Have a passion for leveraging the latest AI tools to drive developer productivity and engineering effectiveness
• Experience making data-driven decisions about team composition and hiring
• Strong written and verbal communication skills 

Preferred Experience 

• Experience establishing engineering standards, procedures, and tools that scale
• Specific experience with Angular, .NET Core C#, and Python
• Business analyst capabilities to progressively elaborate requirements and user stories
• Familiarity with ITIL processes for Incident, Problem, and Change Management and meeting customer support Service Level Agreements (SLAs)
• Track record of successfully recruiting and onboarding exceptional engineering talent
• Agile/Scrum and/or Project Management certifications desired (CSM, PSM, SAFe, or similar) 

Education/Training, Qualifications, and Certification 

• Minimum of a Bachelor's Degree in Computer Science or similar technical/engineering degree and 15 years experience, OR
• Minimum of Master's Degree in Computer Science or similar technical/engineering degree with 12 years of professional experience, OR
• Non-degree - minimum of 20 years experience in IT
• Must be a US Citizen and capable of passing a background check and random periodic drug testing 

Why Join RegScale? 

This is a career-defining opportunity for an engineering leader who wants to make a significant impact. You'll have the autonomy to implement the changes needed to build an elite engineering organization, backed by leadership support and the resources to succeed. Our equity package reflects the transformational impact this role will have on the company's trajectory. 

If you're passionate about taking engineering teams to the next level, love seeing measurable improvements in delivery and quality, and want to be part of a fast-growing cybersecurity startup disrupting the risk and compliance industry—we're excited to have you on our team.