Cranston AI

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

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. About the role 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. What you will do Own core product workflows for tax prep, tax review, bookkeeping, client requests, and practice-management operations. Design and build product abstractions that turn messy accounting work into repeatable, reviewable systems. Use Cranston's internal agent platform to move from product context to working software quickly, then inspect the result until it is right. Build interfaces, workflow states, data models, and agent behavior that hold up in live customer usage. Codify repeatable patterns from customer deployments back into the main product. Use the product yourself, inspect logs and data when needed, notice what is wrong, and push until the details are right. What you will do in your first 30 days Learn how CPA firms move work from source documents to reviewed tax packages, books, and client follow-ups. Shadow existing Cranston workflows and identify places where better product behavior would remove real manual work. Pick workflows and turn them into a concrete product plan: inputs, user-facing states, edge cases, success criteria, and verification steps. Drive an AI-agent implementation loop from product plan to working feature. Test the workflow yourself against real or realistic data, fix the rough edges, and help ship it into a live customer or internal operator workflow. You may be a good fit if you have strong programming skills and have shipped production applications, serious internal tools, or customer-facing automation. high agency and can navigate ambiguity in messy customer environments where the problem is not handed to you cleanly. an ownership mentality and are willing to do whatever it takes to make something work good communication skills - to clearly enough to explain technical tradeoffs, or earn trust with non-technical stakeholders comfort using AI coding agents as your main implementation tool and holding their output to a high bar. Nice to have Experience in accounting, finance, tax, audit, professional services, or another workflow-heavy enterprise vertical. Previous founder experience or meaningful ownership at an early-stage startup. 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 and at ReMatter and Databricks, seeing how much labor still sits on top of even the best systems of record. Max ran an accounting firm that filed 10,000+ tax returns and saw the same problem from inside the work itself: firms losing their best hours to document chasing, data entry, reconciliations, cleanup, and handoffs. Our view is that the