12+ years of experience in operations, strategy, or chief of staff roles in high-growth tech environments.
Experience as a CEO's chief of staff or leading organizational transformations is a strong plus.
Proven track record of driving complex, cross-functional initiatives without direct authority.
Ability to operate as an intellectual peer to senior executives and challenge the CEO when necessary.
Exceptional written and verbal communication skills, with a knack for simplifying complexity.
Strong organizational skills and resilience in managing ambiguity and shifting priorities.
Fluency in AI applications and insights on its impact on company operations.
Responsibilities
Translate leadership decisions into coordinated actions and track execution.
Identify and surface key questions, risks, and organizational constraints early.
Resolve duplicated work and cross-functional conflicts by ensuring clear ownership.
Enhance the senior leadership team's operating rhythm and decision-making processes.
Improve information flow to and from the CEO for better context and action.
Lead priority initiatives without a designated functional home, collaborating with accountable leaders.
Benefits
Opportunity to work closely with the CEO and senior leadership team.
Engagement in high-stakes, impactful projects that shape company direction.
Dynamic work environment in a high-growth technology setting.
Potential for professional growth and development in a strategic role.
Full Job Description
About the role
As Chief of Staff to the CEO, you will be a second set of eyes on the whole business and close the gap between leadership decisions and organizational action. You will identify consequential questions, emerging risks, and conflicts across teams early, form a point of view, and ensure they are addressed by the right leaders. You will also help the company act on leadership decisions quickly, consistently, and with clear ownership. This is neither an administrative role nor the owner of company strategy; you will sharpen and pressure-test the senior leadership team's direction while improving how the company acts on it.
What you'll do
Translate senior leadership decisions into coordinated action by clarifying what was decided, identifying the teams affected, sequencing communication, and tracking execution.
Surface consequential questions, organizational constraints, and emerging risks early, and persist until the appropriate leaders address them.
Identify duplicated work, conflicting roadmaps, and cross-functional problems that lack clear ownership, then ensure they are resolved by the right teams.
Own and continually improve the senior leadership team's operating rhythm, including how priorities are reviewed, decisions are made, and commitments are tracked.
Improve the quality and flow of information to and from the CEO so leaders have the context they need to act.
Lead a small number of CEO-priority efforts without a natural functional home, partnering with accountable leaders to move them through completion.
In order to be successful, you must bring
12+ years of experience across operations, business operations, strategy, general management, or a chief of staff function in high-growth technology environments. Prior experience as a CEO's chief of staff, leading an integration or organizational transformation, or scaling operations through a significant period of growth is a strong plus.
Evidence of entrepreneurial ownership, whether as a founder, early-stage operator, or internal builder who has led an ambiguous, high-stakes mandate from definition through execution.
A track record of driving complex, cross-functional initiatives to completion without relying on direct authority, title, or headcount.
The credibility, judgment, and low ego to operate as an intellectual peer to senior executives, form and press a clear point of view, challenge the CEO, and deliver difficult messages directly.
Exceptional written and verbal communication, with the ability to compress complexity into clear, actionable direction quickly.
Exceptional organization, resilience, discretion, and follow-through, with the ability to create structure amid ambiguity and changing priorities.
Fluency using AI in your own work and a well-developed perspective on how AI should change the way a company like Thumbtack operates.
Expected salary ranges
For candidates living in San Francisco / Bay Area, San Jose, New York City, or Seattle metros, the expected salary range for the role is currently $338,000 - $413,000.
For candidates living in Austin, TX or Washington DC metros or in California, Massachusetts, New Jersey, or Washington states, the expected salary range for the role is currently $304,000 - $371,000.
For candidates living in all other US locations, the expected salary range for this role is currently $287,000 - $351,000.
Actual offered salaries will vary and will be based on various factors, such as calibrated job level, qualifications, skills, competencies, and proficiency for the role.
About Thumbtack, Inc.
Thumbtack is an online marketplace that connects consumers with local professionals for various services, such as home improvement, events, and wellness. The company was founded in 2008 by Marco Zappacosta, Jonathan Swanson, and Sander Daniels, and has since grown to serve millions of customers across the United States. Thumbtack uses a proprietary matching algorithm to connect customers with the best professionals for their needs, and offers a range of tools to help professionals manage their businesses. The company has raised over $400 million in funding from investors such as Sequoia Capital, Google Capital, and Tiger Global Management.
