Chief of Staff

Tebra

8d • Remote

About The Position

The Chief of Staff is a strategic force multiplier for the CEO. While our Executive Assistant (already in place) ensures the CEO’s time and logistics are optimized, the Chief of Staff ensures the CEO’s priorities are executed across the organization. You will operate as a trusted proxy for the CEO—stepping into rooms, driving decisions, and connecting dots across functions that no one else is positioned to see. This is a senior, high-altitude leadership role designed for a strategic operator who wants broad organizational impact and a seat at the table during Tebra’s next phase of growth.

Requirements

• Relevant Experience: 7 to 15+ years of professional experience, with meaningful time spent in management consulting, corporate strategy, business operations, or a prior Chief of Staff role.
• Strategic Altitude: The ability to think strategically while remaining comfortable in the "weeds" of tactical execution.
• Influence without Authority: A proven ability to drive outcomes and lead cross-functional initiatives through people who do not report to you.
• Analytical Rigor: Proficiency with financial models, operational metrics, and data-driven decision-making.
• Executive Presence: The credibility and communication skills to represent the CEO in high-stakes settings with the board, customers, or the executive team.
• Radical Candor: The ability to build a deep trust relationship with the CEO that allows for honest, two-way feedback.
• AI and automation fluency: understands how AI tools can drive operational efficiency and can credibly lead adoption across non-technical functions.

Nice To Haves

• SaaS Background: A strong track record in B2B software or SaaS environments is strongly preferred.
• Education: An MBA or equivalent advanced degree is preferred, though strong operating experience is highly valued.

Responsibilities

• Strategic Planning and Execution: Translate board and CEO priorities into company-wide operating plans and lead the quarterly/annual planning cadence.
• Executive Team Effectiveness: Design and facilitate leadership team meetings to ensure follow-through on decisions and identify organizational friction early.
• Strategic Program Management: Own the cross-functional execution of Tebra’s most critical, multi-year strategic initiatives to drive growth.
• Board and Investor Relations: Partner with the CEO and CFO to build board decks, draft investor communications, and manage the cadence of content.
• Internal Communications: Shape the CEO’s internal narrative, draft all-hands talking points, and ensure consistent messaging across the leadership team.
• Special Projects: Serve as the CEO’s “fixer” for high-stakes problems, such as competitive analysis, M&A strategy, and organizational design.
• Decision-Making Support: Synthesize complex information into clear recommendations to allow the CEO to make high-quality decisions quickly.
• Organizational Health: Keep a pulse on culture, morale, and emerging issues that may not surface through normal reporting channels.

Benefits

• United States: In addition to our healthcare benefits, we also offer amazing perks! Need work from home basics? We offer a discount through Dell! We also offer a number of resources to help you keep your mind and body healthy. Check out Gympass for a great workout, or TelusEmployee Assistance Program to find mental health resources, along with other resources for everyday occurrences.
• Costa Rica: To assist with all of life’s needs, Tebra also offers a wellness and childcare subsidy and a University/Education discount! We also offer a number of resources to help you keep your mind and body healthy. Check out Gympass for access to health and fitness apps, or Telus Employee Assistance Program to find mental health resources, along with other resources for everyday occurrences.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 11-50 employees