Deputy Chief of Staff

Deputy Chief of Staff

Location

Remote Position Type: 1099 Independent Contractor

About the Opportunity

We are seeking an experienced and highly accomplished Deputy Chief of Staff to partner with executive leadership on strategic initiatives, operational excellence, and organizational growth.

This is a unique opportunity for a seasoned professional who enjoys solving complex problems, building scalable processes, and driving meaningful results. The ideal candidate is a self-starter who thrives in fast-paced environments, operates with a high degree of autonomy, and serves as a trusted strategic partner to leadership.

As an independent contractor, you will work closely with executive leadership to help execute high-impact initiatives, improve operations, and support key business objectives while maintaining the flexibility and independence expected of a contractor relationship.

What You'll Be Responsible For

• Partner with executive leadership on strategic initiatives and organizational priorities.
• Lead high-impact projects from planning through execution.
• Identify opportunities to improve operational efficiency and implement scalable solutions.
• Coordinate cross-functional initiatives and ensure projects continue moving forward.
• Develop processes, workflows, and documentation that improve organizational effectiveness.
• Conduct research, gather data, and provide recommendations to support executive decision-making.
• Prepare executive reports, presentations, and strategic planning materials.
• Monitor project milestones, identify potential risks, and proactively recommend solutions.
• Assist with executive-level planning, special projects, and business initiatives.
• Serve as a trusted advisor while maintaining the highest level of professionalism and confidentiality.
• Build strong working relationships across departments and help ensure alignment on organizational priorities.

What We're Looking For

• 7+ years of executive operations, business operations, project management, consulting, or leadership experience.
• Experience supporting founders, CEOs, executives, or senior leadership teams.
• Strong business acumen and exceptional problem-solving skills.
• Outstanding organizational and project management abilities.
• Excellent written and verbal communication skills.
• Ability to manage multiple priorities with minimal oversight.
• High level of discretion and sound judgment.
• Experience improving processes and driving operational efficiency.
• Advanced proficiency with Google Workspace and modern project management platforms.
• A proactive mindset with the ability to anticipate needs and execute independently.

Ideal Candidate

The successful candidate is someone who naturally takes ownership, enjoys building systems, and has the confidence to lead initiatives while collaborating effectively with executive leadership.

We're looking for someone who:

• Thinks strategically and executes effectively.
• Is resourceful and solutions-oriented.
• Brings structure to complex projects.
• Communicates professionally and confidently.
• Operates with integrity and discretion.
• Takes initiative without waiting to be directed.
• Enjoys creating order, improving processes, and driving results.

Independent Contractor Relationship

This opportunity is offered as a 1099 independent contractor position. As an independent contractor, you will be responsible for your own tax reporting, insurance, and business-related expenses in accordance with applicable laws and regulations. While this engagement does not constitute employment, we value our independent contractors as trusted partners and look forward to working together in a collaborative and professional relationship.

Why This Opportunity?

This role offers the opportunity to work directly alongside executive leadership, contribute to meaningful organizational initiatives, and make a measurable impact on the continued growth and success of the organization. If you are a strategic thinker who enjoys building, improving, and executing at a high level, we'd love to hear from you.

Pay: $75,000.00 - $80,000.00 per year

Application Question(s)

• How many years of experience do you have supporting C-suite executives or senior leadership?
• How many years of project management experience do you have?
• Have you led cross-functional initiatives involving multiple departments?
• Have you developed or improved operational processes that increased efficiency or productivity?
• Briefly describe the highest-level executive you've directly supported and your primary responsibilities.
• Tell us about a project you're most proud of leading. What was your role, and what was the outcome?
• What project management platforms, CRMs, or operational software are you proficient in?

Work Location: Remote