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

Job Title Chief of Staff Salary $140k-$200k Equity Company Description Cranston AI is a YC F25 startup that has raised $4M to build AI-native software for the massive and complex accounting industry. Job Description 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. Location San Francisco, USA Why this role is remarkable 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. What You Will Do 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. The ideal candidate 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. #J-18808-Ljbffr Jack & Jill