Chief of Staff

About the role

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 accountants 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.

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.

Why Cranston

• Founders who have built in this market before.
• $4M+ raised from top investors.
• Dozens of customers, with revenue growing quickly.
• A huge, messy market where the right AI-native company can become very large.

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 for accounting firms.
• 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.

Who we are looking for

• You have 3+ years of 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.

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.

Compensation

• The compensation range for this role is $140,000-$200,000 base + equity.