Chief of Staff

Workhelix • San Francisco, CA

18d

About The Position

Workhelix is seeking a hands-on Chief of Staff to work closely with the CEO and help the company operate effectively as it grows. Reporting directly to the CEO, this person will serve as a trusted thought partner and proxy, turning the CEO’s intent into scoped workstreams with clear ownership, timelines, and follow-through. The role oversees Business Operations, establishes the company’s operating rhythm, and drives high-priority initiatives from start to finish. Administrative support remains with the CEO’s Executive Assistant.

The work spans executive alignment, strategic project leadership, and confidential communications. The Chief of Staff will collaborate with the leadership team and customers and, in some cases, investors. The role requires sound judgment, discretion, initiative, and the ability to create structure and make progress in ambiguous situations.

Workhelix is an enterprise SaaS company focused on helping organizations realize value from AI investments through expertise in economics, AI, and data science, including methods for identifying GenAI opportunities and monitoring their return on investment.

Requirements

• At least 5 years in a high-agency role such as startup operations, management consulting, investment banking, venture capital, or strategy and business operations, with ownership of ambiguous, high-stakes work from start to finish.
• Strong analytical and data fluency, including comfort with spreadsheets, model building, and data-based reasoning.
• Ability to collaborate across functions and earn trust without formal authority.
• Strong written and verbal communication skills, including the ability to write concise memos and represent the CEO in meetings.
• High ownership, sound judgment with sensitive information, and discretion.
• Ability to work in ambiguity, create structure, and build repeatable processes for recurring work.
• Candor and a low-ego approach focused on improving the CEO’s and team’s effectiveness.
• Enthusiasm for startup ambiguity, variety, and building culture through operating rituals, communication, and follow-through.

Nice To Haves

• Early-stage startup operating experience.
• Founder experience.
• Prior Chief of Staff experience at a venture-backed startup.
• Experience at a B2B or enterprise software company, ideally in AI.
• Exposure to board meetings, fundraising, or investor relations.
• Technology startup founder experience.
• Experience with M&A, corporate development, or executive recruiting.
• Interest in how AI changes the way companies work.

Responsibilities

• Act as an extension of the CEO and trusted sounding board, represent the CEO when needed, make decisions on the CEO’s behalf, and translate the CEO’s intent into workstreams with owners, timelines, and follow-through.
• Determine what requires the CEO’s attention and handle other matters, while preparing the CEO for board meetings, investor conversations, and high-stakes decisions.
• Gather and synthesize metrics, initiative updates, and team input into a clear view of priorities.
• Own leadership meetings, weekly business reviews, and OKR planning cycles; set agendas, surface relevant data, and drive decisions to completion.
• Own internal and investor communications, including running All Hands, drafting quarterly investor updates, and preparing board materials with the CEO.
• Temporarily own high-priority cross-functional problems and work across Sales, Marketing, Forward-Deployed Teams, Product, and Engineering until lasting fixes and permanent owners are established.
• Deliver special projects end to end.
• Develop and maintain operating processes and materials, including meeting cadence, templates, and a decision log.

Benefits

• Competitive compensation package and benefits.
• Opportunity to learn and collaborate with researchers in AI and the digital economy.
• Opportunity to help build a company, culture, and products from the ground up.
• High-trust, high-autonomy work environment.
• Team that values healthy working practices.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed