Chief of Staff, Engineering (Remote)

Rula; Northern (KY); Hybrid; USD 150,000 - 210,000; Full time

Benefits offered by this job

100% remote work environment

Attractive pay and benefits

Comprehensive health benefits

401(k) plan access

Generous time-off policies

Paid parental leave

Employee Assistance Program (EAP)

Quarterly department stipend

Community and ERGs

Home office stipend: $50 monthly

Wellness program stipend

Job summary

Rula is a remote-first company hiring a Chief of Staff to the Head of Engineering. You will shape how the Engineering org operates, make strategy actionable, and drive cross-functional execution.

You will partner with senior technical leaders to translate vision into concrete priorities and measurable outcomes. You will bring deep engineering experience, executive communication skills, and a track record of diagnosing organizational challenges and delivering impact, including applying AI to

Qualifications

• 12+ years of related professional experience in software
• Direct engineering/EM/technical program leadership experience
• Experience as Chief of Staff to a CTO/Head of Engineering or similar
• Proven ability to diagnose problems and drive execution
• Outstanding communication and ability to influence senior leaders
• Turn unstructured challenges into repeatable practices
• Translate company and technology strategy into priorities and plans
• Fluent with AI tools and applying AI to processes

Responsibilities

• Shape how Engineering operates, decisions, and goals
• Own key operational rhythms and cross-functional execution
• Drive execution by turning high-level vision into plans
• Leverage AI to reduce toil and improve efficiency across the department

Skills

Engineering leadership

Executive communication

Strategic partnering

Cross-functional collaboration

Org design

Execution ownership

CTO liaison

Software engineering

AI tooling

Job description

We believe that mental health is just as important as physical health. We recognize that mental health issues can be complex and multifaceted, and we are dedicated to treating the whole person, not just the symptoms.

We aim to create a world where mental health is no longer stigmatized or marginalized, but rather is embraced as an integral part of one's overall well-being.

We believe that by providing quality care that is both evidence-based and compassionate, we can empower individuals to take charge of their mental health and achieve their full potential. We are passionate about making a positive impact on the lives of those struggling with mental health issues and we strive to be a force for positive change in the field of mental healthcare.

Rula is a remote-first company. We currently hire in most U.S. states, with the exception of Hawaii.

About the Role

As Rula enters a pivotal phase of growth, our Engineering organization is expanding and scaling rapidly this year. To guide this evolution, we are 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.

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

While having the preferred qualifications enhances your candidacy, having all of them is not mandatory. We encourage all interested applicants to apply, even those who may not meet every preferred requirement.

• 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)

We're serious about your well-being! As part of our team, full-time employees receive:

• 100% remote work environment: Working hours to support a healthy work-life balance, ensuring you can meet both professional and personal commitments (must be based in United States, currently not hiring in Hawaii)
• Attractive pay and benefits: Full transparency of pay ranges regardless of where you live in the United States
• 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 (for most employees)
• 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: Participate in groups that celebrate employee identity and lived experiences, fostering a sense of community and belonging for all
• 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

Our team

We believe that diversity, equity, and inclusion are fundamental to our mission of making mental healthcare work for everyone. We are dedicated to having a culture of inclusion that will support our employees in feeling safe, seen, heard, and valued.