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

She will pick the best candidates from Jack’s network.

The next step is to speak to Jack.

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.

Who are Jack & Jill?

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.

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.

How does this work?

• 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 it’s a match and the company wants to meet you, they’ll make the intro. In the meantime, if you’d like, Jack will send you excellent alternatives.

We never post fake jobs

This isn’t a trick. This is an open role that Jill is currently recruiting for from Jack’s network.

Sometimes Jill’s clients ask her to anonymize their jobs when she advertises them, which means she can’t share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn’t much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we’re giving his services away for free.