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About the role

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 important projects from first principles: customer discovery, sales ops, onboarding workflows, internal systems, GTM experiments, and hiring processes. Some weeks you will be talking to accounting firms and helping shape our GTM motion. Other weeks you will be turning an overwhelmed 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. 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 naturally command ownership. You should be comfortable jumping between sales calls, customer context, spreadsheets, AI tools, product feedback, hiring funnels, and founder priorities without needing a predefined 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.
About the role
Cranston is building the AI back office for accounting firms, combining the judgment of experienced operators with the leverage of AI agents and reliable software.
We automate the most complex manual workflows inside CPA firms: tax preparation, bookkeeping, document collection, cleanup, review, close, and client operations.
Cranston is already deployed with accounting firms across the country, helping them serve more clients, reduce bottlenecks, and give their best people time back for higher-value work.
You will work across product, design, engineering, and implementation. Some days that means mapping how tax packages move through a firm. Other days it means building a review workflow, designing an agent loop, tightening data models, or debugging why a customer workflow failed in production.
This is a product engineering role for someone who wants to build the system, not just spec it. You will turn what we learn from firms into durable product: interfaces, automations, review loops, workflow primitives, data models, and agent behavior that work across customers.
Cranston is vertically integrated across software, AI agents, and managed back-office operations. That makes the problems unusually concrete: if the product is wrong, the work breaks. If the product is right, firms can take on more clients without adding headcount.
Why Cranston
- Cranston was founded by Sean O'Bannon and Max Minsker to rebuild the accounting firm back office from the ground up.
- Sean previously built ERP and ML systems at ReMatter and Databricks, seeing how much labor still sits on top of even the best systems of record. Max ran an accounting firm t","datePosted":"2026-07-07","employmentType":"FULL_TIME","hiringOrganization":{"@type":"Organization","name":"Cranston AI","sameAs":"https://www.cranstonai.com/"},"url":"https://jobs.ashbyhq.com/cranston/1498c493-e1ef-4fb6-98a0-e97cf8fa0808","jobLocationType":"TELECOMMUTE","jobLocation":{"@type":"Place","address":{"@type":"PostalAddress","addressLocality":"San Francisco"}}}]

About the role

What you will do

Why Cranston

Cranston AI

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