Chief of Staff ($140k-$200k + Equity) at Cranston AI

Job Title

Chief of Staff

$140k-$200k Equity

Cranston AI is a YC F25 startup that has raised $4M to build AI-native software for the massive and complex accounting industry.

As employee #3 at Cranston AI, you will work directly with the founders to scale operations, go-to-market motions, and customer onboarding. This high-leverage role is designed for a high-agency operator ready to turn ambiguity into execution while building the foundational systems for an AI-native accounting platform that already generates significant MRR.

San Francisco, USA

• Work as employee #3 alongside founders from Stanford CS and successful accounting backgrounds, gaining front-row access to early-stage scaling.
• Join a YC F25 startup with exceptional momentum, having reached over $21k MRR within its first 60 days of operation.
• Participate in the massive transformation of the accounting industry using AI-native tools, backed by over $4M in seed funding.

• Lead customer onboarding and implementation projects from initial kickoff through successful product adoption and usage.
• Build and manage the company’s go-to-market motion, including research, sales operations, and CRM pipeline management.
• Translate founder vision into concrete operating systems, written plans, and dashboards to resolve organizational bottlenecks.

• Proven track record in operations, consulting, or high-growth startups with a focus on execution and process development.
• Exceptional analytical skills with the ability to manage complex workflows, spreadsheets, and AI-driven productivity tools.
• High-agency mindset characterized by relentless follow-through and the ability to solve problems without needing a predefined playbook.