Chief of Staff

Cranston AI is building AI-native software for accounting.

We are hiring a Chief of Staff to work directly with the founders across operations, go-to-market, customer onboarding, and whatever else most urgently needs to get done. This is a high-ownership role for someone who wants to sit close to the center of a fast-moving company and turn ambiguity into shipped work.

This is not a note-taking job. You will own messy, important projects from first principles: customer discovery, sales ops, onboarding workflows, internal systems, GTM experiments, hiring processes, founder follow-through, and operational fire drills. Some weeks you will be talking to accounting firms and helping shape our GTM motion. Other weeks you will be turning a broken internal workflow into a reliable process, driving a customer implementation forward, or building the operating cadence that keeps the company moving.

We work in accounting, which is a large and tricky professional-services market. The work is operationally dense, detail-heavy, and full of judgment calls. That makes it a strong fit for AI, but only if the company has the taste and execution discipline to build around the real workflow instead of shipping demos. Your job is to help us move faster without letting important things fall through the cracks.

You will be effective here if you are sharp, organized, direct, and allergic to vague ownership. You should be comfortable jumping between sales calls, customer context, spreadsheets, AI tools, product feedback, hiring funnels, and founder priorities without needing a perfect playbook.

What You Will Do

• Work directly with the founders on the highest-priority operational and GTM projects.
• Help build and run our go-to-market motion.
• Own customer onboarding and implementation projects from kickoff to successful usage.
• Run research, outreach, sales ops, CRM hygiene, follow-ups, and pipeline process.
• Turn founder intent into written plans, operating systems, dashboards, and executed work.
• Identify bottlenecks across product, sales, support, and operations, then fix them.
• Build lightweight internal processes that make the company faster instead of more bureaucratic.
• Use AI tools aggressively to create leverage in research, ops, analysis, documentation, and implementation.

You Might Be a Fit If

• You have experience in operations, consulting, startups, GTM, finance, accounting, customer success, or a similarly execution-heavy role.
• You are unusually good at taking a vague problem and producing a concrete next action.
• You can write clearly, follow up relentlessly, and keep track of details without needing to be managed.
• You are comfortable talking to customers and asking specific questions until the real problem is obvious.
• You are analytical enough to work with spreadsheets, metrics, workflows, and operational systems.
• You are high-agency: when something is broken, you do not wait around for someone to assign you the fix.
• You like early-stage startup intensity and understand that the job changes as the company changes.
• You have strong judgment about when to move fast, when to be precise, and when to escalate.

Bonus Points

• You have worked at an early-stage startup.
• You have experience in accounting, finance, bookkeeping, tax, audit, or professional services.
• You have helped build or run a B2B sales or customer onboarding motion.
• You are very good with AI tools and can use them to move substantially faster.
• You have been a founder, operator, consultant, investor, or chief-of-staff type before.

Compensation

Salary: $90,000 - $150,000, based on experience and scope.

We care less about polished credentials and more about whether you can take ownership, communicate clearly, and drive important work to completion.

Interview Process

1. Intro call with a founder focused on your background, judgment, and what kind of operating work you have owned before.
2. Practical work sample based on a real Cranston problem, likely involving customer context, GTM process, or operational prioritization.
3. Founder working session.
4. References and offer.