Customer Implementation Lead

ABOUT CRANSTON Cranston builds AI that does tax and accounting work for CPA firms, inside the software those firms already use. Accounting firms use Cranston today for tax preparation, bookkeeping, document collection, review, and client work. We are a small team in San Francisco. Dozens of firms already use the product, and demand is growing quickly. We need someone to make every new customer successful and build the operating system for repeatable onboarding. ABOUT THE ROLE As a Customer Implementation Lead, you will own the customer journey from signed contract through confident daily use. You will be the quarterback for each launch: turn customer goals into a clear plan, keep internal and external teams aligned, lead training, and make sure the workflow works in real firm work. You do not need to be an accounting expert on day one. You do need to be organized, curious, comfortable with software, and willing to learn how accounting firms work. You will partner closely with Cranston's Forward Deployed Accountants when a workflow calls for deeper accounting judgment. WHAT YOU'LL DO - Own onboarding for new accounting-firm customers, from discovery and kickoff through go-live and early adoption. - Run discovery sessions, define scope, map milestones, assign owners, and set clear success measures. - Build practical implementation plans that keep customer and Cranston teams moving together. - Coordinate configuration, data collection, testing, training, and launch readiness across multiple concurrent projects. - Lead customer kickoffs, working sessions, status updates, and training for partners, managers, preparers, bookkeepers, and administrative staff. - Track risks, dependencies, and open questions. Surface problems early and drive them to resolution. - Work inside the product with customers. Diagnose workflow issues, find practical workarounds, and coordinate with product and engineering when the product needs to improve. - Create onboarding playbooks, templates, training materials, and repeatable operating rhythms as we scale. - Bring the customer's voice to product and engineering with specific examples, patterns, and recommendations. - Support a smooth transition from onboarding into ongoing customer success, adoption, and expansion. - Travel occasionally when being in the room will make customer work better. YOUR FIRST 90 DAYS - Learn Cranston deeply enough to run a customer workflow yourself, from source documents through review and delivery. - Shadow current onboarding work, then take ownership of new firm launches. - Build a clear implementation plan and training approach that customers can reuse. - Create a practical feedback loop between customers and the product team, with examples engineers can reproduce. - Help several firms reach confident, repeatable use of Cranston in live client work. WHO WE'RE LOOKING FOR - You have 3+ years of experience in implementation, onboarding, customer success, professional services, consulting, operations, or project management for B2B software. - You can manage several customer projects at once without dropping details or losing momentum. - You are a clear, thoughtful communicator who can work with executives, operators, and technical teammates. - You are comfortable learning software quickly and turning an unfamiliar workflow into a simple plan. - You are good at teaching. You notice when someone is stuck and help them move forward without making them feel behind. - You have high ownership, strong follow-through, and the judgment to escalate risks early. - You are curious about accounting and finance, even if you have not worked in the profession before. - You are excited to work in person with the team in San Francisco and travel occasionally when customer work calls for it. BONUS POINTS - Experience in accounting, finance, tax, audit, payroll, ERP, or another workflow-heavy industry. - Experience implementing accounting, tax, or practice-management software. - Experience leading change management, training, or process improvement. - Experience at an early-stage company where you built the playbook while doing the work. - Experience using AI tools to move faster and improve customer outcomes. COMPENSATION - $120K-$160K base salary - 0.05%-0.20% equity depending on experience - Health, dental, and vision benefits