Founding Strategy & Operations

Founding Strategy & Operations

Cranston · San Francisco · In person

Compensation: $160,000–$190,000 base + equity

Cranston is building AI tax-preparation and review software for CPA firms. We’re a seven-person startup looking for an exceptional generalist to work directly with our founders and own how customers put our product to work.

This role requires someone who learns quickly, asks sharp questions, earns people’s trust, and follows through. You’ll get deeply familiar with our customers’ businesses, solve unfamiliar problems, and turn what you learn into better software and better ways of operating.

You don’t need to have worked in customer success, implementation, or tax. You do need a track record of taking on difficult work and making things happen.

Your first major responsibility will be helping accounting firms successfully adopt Cranston. You’ll work directly with firm owners and their teams, understand their workflows, guide them through the product, and resolve the obstacles that stand between a signed contract and productive use. Along the way, you’ll help shape our product and build the processes that allow us to grow.

• Own customer outcomes. Understand what each firm needs, build a practical plan, and drive it through to completion.

• Solve messy problems. Investigate issues, distinguish symptoms from root causes, and work with engineering to get the right things fixed.

• Build trust. Run thoughtful customer conversations, explain complicated ideas clearly, and follow through on commitments.

• Make the product better. Recognize patterns across customers and translate them into clear product recommendations.

• Build how we operate. Create useful tools, processes, and documentation that make the next customer’s experience better.

• Take on emerging priorities. Work with the founders on important operational problems as the company’s needs evolve.

Early on, a substantial majority of your time will involve customers directly: calls, training, troubleshooting, and keeping projects moving. You should enjoy that work and be excited to improve how it gets done.

• You get up to speed quickly in unfamiliar domains.

• You can break an ambiguous problem into concrete steps and start making progress.

• You’ve owned something difficult and can explain what you personally did, what changed, and what you learned.

• You communicate clearly and listen carefully. You can build credibility with a business owner and collaborate effectively with an engineer.

• You’re comfortable with numbers, spreadsheets, new software, and AI tools.

• You take initiative, care about details, and finish what you start.

• You’re equally willing to make an important decision and handle the small task needed to move things forward.

Your background might include consulting, startup operations, product, investment banking, private equity, venture capital, or building something yourself. We expect many candidates to have roughly 2–5 years of professional experience, but we care most about your accomplishments and how you work.

You’ll work directly with the founders in a small team where your judgment and execution matter. You’ll have ownership of an essential part of the business, direct exposure to customers, and meaningful influence on what we build.

As you deliver results, your responsibilities can grow with the company. This is an opportunity to help build a business from an early stage and develop the judgment that comes from owning real outcomes.

To apply, tell us about something difficult you took ownership of: the problem, what you did, and the result.