Chief of Staff, Engineering - Rula

Rula is a remote-first company dedicated to treating the whole person and making mental healthcare work for everyone. We are expanding rapidly and hiring a Chief of Staff to serve as a senior organizational leader and strategic partner to the Head of Engineering and the Engineering Leadership Team.

About the Role

In this role, you will help shape how Engineering operates, makes decisions, and executes against our most critical goals. Rather than leading through formal authority, you will drive impact through influence, collaboration, and sharp organizational insight. You will own key operational rhythms while tackling ambiguous challenges, diagnosing friction, and designing actionable plans for cross-functional execution.

Beyond day-to-day operations, you will bring innovative thinking to how we work, leveraging modern tools and AI to remove toil across the department. With prior experience inside an engineering organization, you communicate as a strategic peer to senior technical leaders and are energized by turning high-level vision into sustainable organizational success.

Required Qualifications

• 12+ years of related professional experience
• Direct experience as an engineer, EM, or technical program leader inside a software organization (not purely a BizOps/consulting background)
• Demonstrated experience serving as a strategic partner or Chief of Staff to a CTO, Head of Engineering, VP of Engineering, or other senior technical executive
• Proven track record of diagnosing an organizational/operational problem, designing a plan, and handing execution to another owner while tracking progress to completion
• Exceptional communication and interpersonal skills, with demonstrated ability to influence senior leaders, facilitate complex decisions, challenge assumptions constructively, and create alignment across multiple stakeholders
• Navigated fast-moving environments with high adaptability and resourcefulness, rolling up your sleeves to turn unstructured challenges into clear, repeatable practices without relying on a pre-existing corporate playbook
• Proven ability to translate company and technology strategy into clear organizational priorities, operating plans, and measurable outcomes, moving fluidly between strategic thinking and hands-on execution
• Demonstrated personal fluency with AI tools in daily work, including experience applying AI to redesign or improve an organizational process

Preferred Qualifications

• Previous experience specifically in a Chief of Staff, Engineering Operations, or similar title reporting to a CTO/Head of Engineering/VP of Engineering
• Experience operating inside a high-growth or rapidly scaling technology company
• Experience within healthcare technology or another highly regulated or complex industry
• Experience partnering on organizational design, workforce planning, or leading significant change management/transformation initiatives
• Prior individual contributor engineering experience (has personally written and shipped code, not just adjacent program/ops experience)

Benefits & Perks

• 100% remote work environment: Working hours to support a healthy work-life balance across the U.S. (excluding Hawaii)
• Comprehensive health benefits: Medical, dental, vision, life, disability, and FSA/HSA
• 401(k) plan access: Start saving for your future
• Generous time-off policies: Including 2 company-wide shutdown weeks each year for self-care
• Paid parental leave: Available for all parents, including birthing, non-birthing, adopting, and fostering
• Employee Assistance Program (EAP): Supporting your mental and physical health
• Quarterly department stipend: Fun team-building activities or in-person gatherings
• Community and employee resource groups: Fostering a sense of community and belonging
• Home office stipend: New hire home office stipend & $50 monthly stipend to help cover internet or cell phone expenses
• Wellness at Rula program: Year-round wellness initiatives and a $50/month wellness stipend