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.
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Chief of Staff at Cranston AI
Cranston AI is looking for its third employee to join as Chief of Staff. Working directly with founders from Stanford CS and the accounting industry, you'll help scale a YC F25 startup that hit $21.5K MRR in its first 60 days. If you thrive in fast-paced, ambiguous environments and want to own GTM and operations, this is your chance to join a high-growth team at the ground floor.
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Location
San Francisco, United States
Compensation
$140k-$200k + Equity
Company
Cranston AI
About this role
Role overview
About the company
Cranston AI is a full‑stack AI accounting firm that provides AI software and managed back‑office capacity for CPA firms and accounting teams. Its platform automates key accounting and tax workflows including tax preparation and review, bookkeeping, client requests and follow‑up, practice management, and broader financial analysis. Cranston connects to a firm’s existing systems of record and ingests data from company apps to handle repetitive accounting and compliance work, aiming to replace traditional accounting labor with autonomous AI systems supervised by licensed CPAs. The company focuses on running the back office for CPA firms and for startups and SMBs, helping them reduce accounting costs while increasing speed and accuracy in reconciliation, tax compliance, and ongoing accounting operations.
What you'll do
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.
Who you are
Who this is a fit for
- 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.
Why this role
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.
Jack & Jill
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.
I recruit from Jack’s network and make the intro when I spot a great match.And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
Meet Jack
What happens next?
Jack’s an AI agent for job searching and career coaching. He works for you.
Jill is the AI recruiter working for the company. She recruits from Jack’s network.
If your profile’s a match and Cranston AI wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.