Chief of Staff

Workhelix • San Francisco, CA

14h

About The Position

Workhelix is an enterprise SaaS company focused on helping organizations maximize the value of their AI investments. The Chief of Staff is a highly hands-on role for someone experienced in working closely with a founder or senior executive and bringing structure, accountability, and operational discipline to a fast-growing business.

Reporting directly to the CEO, the Chief of Staff acts as the CEO’s right hand, primary thought partner, and extension. The role owns how Workhelix operates by establishing its operating rhythm, overseeing Business Operations, and driving high-priority initiatives from start to finish. It translates strategy into plans, accountable owners, and results. Administrative support remains with the CEO’s Executive Assistant.

The work spans executive alignment, strategic project leadership, and confidential communications. The Chief of Staff works closely with the leadership team and customers, and sometimes with investors. The role calls for a high-drive, resourceful operator who can solve problems, organize independently, thrive amid ambiguity, and help Workhelix advance to its next stage.

Success includes building strong relationships with leaders and understanding their goals, metrics, and blockers; taking ownership of leadership meetings, business reviews, OKR cycles, board preparation, and investor communications; and delivering special projects with lasting results. The role also establishes an operating playbook—including meeting cadence, templates, and a decision log—that can run without the Chief of Staff.

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 end to end.
• Strong analytical and data fluency, including comfort with spreadsheets, building models, and reasoning from data.
• AI-native approach, using modern AI tools to work faster and go deeper.
• Track record of collaborating across functions and earning trust without formal authority.
• Strong written and verbal communication skills, including the ability to write crisp memos and represent the CEO in meetings.
• High ownership, sound judgment and discretion with sensitive information, and enthusiasm for startup ambiguity and variety.
• Ability to grow one’s mandate by turning undefined problems into systems, decisions, or outcomes the team relies on.
• Ability to build culture through rituals, operating cadence, communication, and follow-through.
• Ability to exercise candor, low ego, clarity, and a systems-first mentality.

Nice To Haves

• Early-stage startup operating experience is strongly preferred.
• Founder experience is a strong plus.
• 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 a trusted sounding board and proxy for the CEO, represent the CEO when needed, make decisions on the CEO’s behalf, and turn the CEO’s intent into scoped workstreams with owners, timelines, and follow-through.
• Protect the CEO’s focus by determining what requires the CEO’s attention, handling other matters, and 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 that informs priorities.
• Own the operating rhythm, including leadership meetings, weekly business reviews, and OKR planning cycles; set agendas, surface relevant data, and drive decisions to closure.
• 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 each has a lasting fix and permanent owner.
• Deliver special projects end to end.
• Build and document operating systems, including meeting cadence, templates, and a decision log.
• Collaborate with the leadership team and customers and, in some cases, investors.

Benefits

• Competitive compensation package and benefits.
• Opportunity to learn and collaborate with researchers in AI and the digital economy, including Andrew Ng, Erik Brynjolfsson, Andy McAfee, and Daniel Rock.
• Opportunity to help build a company, culture, and products from the ground up with a team that values healthy working practices.
• High-trust, high-autonomy work environment.

What This Job Offers

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