Kaizen

Chief of Staff (to CEO)

Remote Full-time

As a Chief of Staff to the CEO, you’ll work directly with the founders on Kaizen’s most important strategic and operational initiatives — spanning go-to-market, strategic finance, business operations, and company building. You’ll act as a force multiplier for the CEO(s): helping turn ideas into plans, plans into execution, and execution into real outcomes.

This is a highly dynamic role at the center of the company. One week you might be analyzing revenue performance or digging into our financials. The next you might be organizing a customer event, preparing materials for investor meetings, or jumping into a GTM initiative to help drive pipeline.

You’re an operator at heart — someone who enjoys rolling up your sleeves and doing whatever it takes to move the company forward.

What You'll Build

  • Strategic initiatives that shape the company — partner with the founders to scope, analyze, and drive projects that materially impact Kaizen’s trajectory (market expansion, partnerships, internal operations, and company strategy).
  • Strategic finance and business insight — help the founders understand how the business is performing by analyzing revenue, pipeline, unit economics, and operational metrics.
  • Business operations infrastructure — design lightweight systems that help the company run smoothly: planning processes, internal dashboards, key metrics, and decision frameworks.
  • Founder leverage — turn high-level ideas or conversations into clear plans, research, and execution. Prepare materials for customer meetings, investors, and internal decision-making.
  • Hands-on GTM support — jump in wherever needed to help grow the business: organizing customer events, supporting outbound campaigns, researching target accounts, preparing sales materials, and refining messaging based on customer conversations.
  • Special projects — own important initiatives end-to-end as they arise, from early exploration to execution.

We're Looking For

  • 1–4 years of experience in consulting, banking, BizOps, strategy, VC, or operating roles at high-growth startups.
  • Operator mindset — you enjoy rolling up your sleeves and solving problems directly, not just advising from the sidelines.
  • Structured thinker — you break down ambiguous problems, build frameworks, and move quickly toward decisions.
  • Analytical — comfortable working with financials, metrics, and data to understand how the business is performing.
  • Exceptional communicator — clear writing and concise thinking. You can distill complex ideas into simple narratives.
  • High agency — you identify problems, take ownership, and push things across the finish line.
  • Comfortable with ambiguity — priorities shift as the company evolves, and you thrive in fast-moving environments.
  • Startup mindset — you’re excited to work closely with founders and help build something from the ground up.

Bonus Points

  • Experience at an early-stage startup (Seed → Series A)
  • Background in consulting, investment banking, venture capital, or strategy roles
  • Experience working closely with founders or senior executives
  • Experience with financial modeling, forecasting, or market analysis
  • Experience organizing events or supporting go-to-market efforts
  • Strong AI fluency — you actively use AI tools to think, analyze, and move faster

What We Offer

  • Meaningful equity in a fast-growing company attacking a massive market
  • Direct exposure to founders and the company’s most important decisions
  • Fast learning environment — see how a company is built from the ground up
  • Competitive compensation — $140K–$190K base salary plus equity
  • Full benefits — health, dental, vision, unlimited PTO
  • San Francisco office — collaborate in-person with the team

🚀 Y Combinator Company Info

Y Combinator Batch: P25
Team Size: 6 employees
Industry: B2B Software and Services
Company Description: Automate anything on the web.

💰 Compensation

Salary Range: $140,000 - $190,000
Equity Range: 0.25% - 0.75%

📋 Job Details

Job Type: Full-time
Experience Level: 1+ years
Engineering Type: Full stack