Jobs at Cranston AI (YC F25) (Now Hiring) — 2 open

About Cranston

Cranston builds AI that does tax and accounting work for CPA firms, inside the software those firms already run. Accounting firms use Cranston today for tax preparation, bookkeeping, and client work.

We're a small team in San Francisco, backed by Y Combinator. Demand has grown past what we can handle while also building the product. We're hiring our first account executive to turn that demand into durable growth and help define how Cranston sells.

Role Overview

You'll step into an active inbound motion and own relationships from the first conversation through signed contract, onboarding, and expansion. This role is a mixture of consultative selling, product fluency, industry curiosity, and relentless follow-through.

Our buyers are owners and partners of CPA firms. They have been pitched bad software for years, and they buy from people who understand their work and earn their trust. You'll learn accounting deeply, demo Cranston with credibility, and become a partner to firms as they adopt AI.

This role is ideal for someone who thrives in early-stage environments, loves building from zero, and wants to help shape the sales motion, product, and customer experience.

What You'll Do

Own the full customer journey — from the first inbound demo to signed contract, onboarding, and a customer confidently running Cranston.

Convert real demand into revenue. Run 15-25 demos a week with owners and partners of accounting firms, understand what matters, and move good opportunities forward with urgency.

Become a product and accounting expert. Demo Cranston credibly, understand the workflows it changes, and translate capability into a clear business case.

Earn trust with skeptical buyers. Listen closely, communicate plainly, and show firms how Cranston fits the way they already work.

Inform the roadmap. Synthesize objections, customer feedback, and market signals. What you learn in the field will shape what we build.

Represent Cranston in the industry. Attend 4-6 accounting conferences a year and build lasting relationships across the profession.

Work AI-native. Use Claude or ChatGPT to prepare calls, draft follow-ups, and keep the CRM current so your time stays focused on customers.

Who You Are

Exceptional on sales calls. You ask sharp questions, listen well, and make buyers feel understood.

A proven closer. You've carried a quota and hit it, with 2-5 years selling B2B software to small or mid-market companies.

High ownership. You follow up the same day, every time, and you don't wait to be told what to do next.

A sharp communicator. You write clearly, present with confidence, and adapt from a working accountant to a firm owner.

AI-native. You already use AI tools in your daily work and keep finding better ways to use them.

Curious about accounting. You're interested in the profession, or willing to get deep into it fast.

Why Cranston

You'll sell a product that accounting firms use today for real tax preparation, bookkeeping, and client work.

You'll inherit real demand and have unusual ownership as the first sales hire.

You'll work directly with the founders and product team. Customer conversations will translate quickly into product decisions.

You'll join a small team at the moment AI is changing how accounting work gets done.

Compensation

• $125-145k base, $180-230k OTE, uncapped

• 0.25-0.5% equity depending on experience

• Variable compensation is guaranteed for the first 90 days and ramps through day 180. We'll set a real quota together once we have six months of data.

• Health, dental, and vision

Process

• 30-minute call with a founder

• 90-minute session where you demo Cranston to us and we play a tough prospect

• A short take-home: turn a call transcript into a follow-up email and deal notes

• Reference checks, where we verify quota numbers

• Offer within two weeks of applying