Chief of Staff

Workhelix · Greater San Francisco Area · $150,000–$215,000 (stated in the posting)

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Role

This is a highly hands-on role for someone who has worked closely with a founder or senior executive and knows how to bring structure, accountability, and operational discipline to a fast-growing business.

Reporting directly to our CEO, you'll be the CEO's right hand and primary thought partner, with full access to our decision-making and internal thinking. You'll own how Workhelix operates by setting the operating rhythm, overseeing Business Operations, and driving our highest-priority initiatives from start to finish. In short, you'll extend the CEO's reach, turning strategy into plans, plans into accountable owners, and owners into results, with administrative support continuing to sit with the CEO's Executive Assistant.

The work spans executive alignment, strategic project leadership, and confidential communications. You'll work closely with our leadership team and customers and, in some cases, our investors.

You're a problem solver and self-organizer who thrives in ambiguity. You want ambitious goals and the freedom to figure out how to reach them. We're looking for a high-drive, high-horsepower operator who is excited to help take Workhelix to the next level.

Key responsibilities

• Turn founder intent into results. Act as a true extension of the CEO: a trusted sounding board and proxy who represents the CEO in rooms he can't be in, makes decisions on their behalf, and turns their intent into scoped workstreams with clear owners, timelines, and follow-through.
• Protect the CEO's focus. Decide what needs the CEO's attention and quietly handle what doesn't. Prepare him for board meetings, investor conversations, and high-stakes decisions.
• Give the CEO a clear picture to act on. Gather and synthesize metrics, initiative updates, and team input into a view that drives priorities.
• Run the operating rhythm. Own leadership meetings, weekly business reviews, and OKR planning cycles. Set agendas, surface the right data, and drive every decision to close.
• Own internal and investor communications. Run All Hands, draft the quarterly investor update, and prepare board materials with the CEO.
• Close the gap between strategy and execution. Step in as temporary owner of the highest-priority cross-functional problems, working across Sales, Marketing, Forward- Deployed Teams, Product, and Engineering until each has a lasting fix and a permanent owner.
• Deliver special projects end to end. 

What we value

• Judgment and discretion. You'll see sensitive information before almost anyone else. People trust you because you protect it.
• Ownership. You notice what's broken and fix it without being asked.
• Clarity. You turn messy inputs into a crisp memo, agenda, or recommendation.
• Comfort with ambiguity. Part of the job is defining the job. You create order instead of waiting for it.
• Systems-first mentality. When something recurs, you build a process so it runs without you.
• Low ego. Your work makes the CEO and the team better. Credit is not the point.
• Candor. You tell the CEO what they need to hear, not what they want to hear.

What you bring

• 5+ years in a high-agency role, such as startup operations, management consulting, investment banking, venture capital, or strategy and business operations, where you owned ambiguous, high-stakes work end to end.
• Early-stage startup operating experience is strongly preferred. Founder experience is a strong plus.
• A track record of growing your own mandate. You've walked into an undefined problem and walked out with a system, decision, or outcome the team now relies on.
• Strong analytical and data fluency. You're comfortable in spreadsheets, building models, and reasoning from data, and you're AI-native, using modern AI tools to move faster and go deeper.
• A track record of collaborating across functions and earning trust without formal authority.
• Energy for building culture through rituals, operating cadence, communication, and follow-through.
• High ownership, sound judgment with sensitive information, and real enthusiasm for startup ambiguity and variety. No two weeks look the same.
• Sharp written and verbal communication. You can write a crisp memo one day and represent the CEO in the room the next.

Nice to have

• 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.

What success looks like

First 30 days

• You've met every leader and understand their goals, metrics, and blockers.
• You've shadowed the CEO across internal meetings, board materials, and customer conversations.
• You've delivered your first synthesis of company priorities and metrics, and the CEO has acted on your recommendations.
• You own the weekly leadership meeting agenda, notes, and action items.
• You and the CEO have agreed in writing on your top priorities for the next 90 days.
• You send the CEO a weekly update on what's done, what's in progress, and what's blocked.

By 60 days

• You run the weekly business review and OKR cycle end to end, and leadership decisions close on schedule.
• You own prep for the next board meeting and the quarterly investor update.
• You're leading your first special project with a clear scope, owner, and deadline.

By 90 days

• Your first special project has delivered a result the team now relies on.
• The operating playbook (meeting cadence, templates, decision log) is documented and runs without you.
• You and the CEO have reviewed the role's scope and agreed on priorities for the next quarter.

Pay range and compensation package $150,000- $215,000 + Equity + Health Benefits

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